HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag

Make a holiday rental houses or villa in Massachusetts your home away from home

Right in the heart of New England, Massachusetts is a wonderfully endearing state, attracting visitors throughout the year, but especially during the hot summer months. Everything you could wish for from a holiday can be found in abundance from a Massachusetts property, from glorious landscapes rich in nature to a coastline lined with stunning beaches, lively cities and excellent sporting facilities.

Things to do in Massachusetts

The mountain resorts of the Berkshire Mountains are hugely attractive, with tourists flocking to ski in Massachusetts during the winter and to walk, ride and mountain bike during the summer. Skiing in Massachusetts is hugely popular, especially in the Berkshire Mountains, where cold winters can usually be guaranteed. Conditions for skiing in Massachusetts are best in February, and although many of the ski resorts are quite small, there is a great range of pistes allowing everyone from advanced skiers to complete beginners to have a wonderful holiday skiing in Massachusetts.

Coastal Massachusetts is attracts many visitors each year, boasting some of New England’s best beaches. There are a huge range of magnificent saltwater fishing spots in Massachusetts, from the Gloucester in the north to Plymouth in the south. It is hard to pick the best beaches in Massachusetts, such is the variety and range of beaches available, but, with 40 miles of beaches, scenic walks and wild nature, Cape Cod has to appear high on the list of the best beaches in Massachusetts. Ipswich Beach, Horseneck Beach and Nantucket Beach would also need a mention on the list of best beaches in Massachusetts too though. Those with a love of nature must take one of the many whale watching trips available from the coastal resorts. A breeching whale is certainly one of the most impressive and awe-inspiring sights in Massachusetts, and one that you will never forget.

The stunning landscapes of Massachusetts are awash with national parks, protecting the rich nature and beautiful sights of Massachusetts for generations to come. There are many miles of walking and hiking routes to take through the countryside, and if you travel to explore the coastal parks, you can find some of the best canoeing, sailing and saltwater fishing spots in Massachusetts. The famous Freedom Trail is the most celebrated walking and hiking route you can tackle from a Massachusetts holiday rental, taking in a range of historic sights in Massachusetts including the Feneuil Marketplace, Paul Revere House and Boston Common.

Golf also thrives in Massachusetts. Golf is one of the most popular sports in Massachusetts, and the excellent courses reflect this. Whether you are a seasoned professional or an absolute beginner, you will easily be able to find a challenging and enjoyable course to play, as well as all the help you can hope for.

When taking a self catering Massachusetts property, it is always a great idea to investigate the events calendar, as there is almost something of interest to investigate in the state. The Theatre Festival in June, Pittsfield Ethnic Fair in August and the Berkshire Summer Arts Festival in July are the most popular events to enjoy from Massachusetts accommodation, but there are many to choose from.

Places to visit on holiday in Massachusetts

Eastern Massachusetts is the jewel in the crown. It is here that the most important cities and sights in Massachusetts are located, including Boston and Cambridge, as well as the parks of the famous Freedom Trail, Fenway Park and the Boston Common.

Martha’s Vineyard offers a little of everything that makes Massachusetts such a popular destination. The beaches are sensational, covered in fine, golden sand, with excellent sailing credentials and some of the best saltwater fishing spots in Massachusetts.

Weather in Massachusetts

The weather in Massachusetts varies greatly from season to season. If you are hoping to ski in Massachusetts, February is the best month as temperatures drop to an average of -6°C, and conditions are sublime. The summer months are hot, with average temperatures reaching around 26°C. This is the time when most visitors travel to Massachusetts accommodation for their holidays, and when the vast majority of events, festivals and fairs are held. The best beaches in Massachusetts can become crowded during this time, but there are plenty to choose from!

Airports in Massachusetts

Although there are many airports in Massachusetts, those travelling from the UK will only be interested in one, Boston International Airport (BOS). Virgin Atlantic, British Airways and Aer Lingus all provide direct flights from the UK to Boston.

Cancel Clear Filters Apply Filters

Property Type

Popular Searches

Payment Options

Facilities

Managed By

Local Area

Property Details

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Massachusetts Holiday Homes & Cottages (300+)

  • 1 - 50 of 300+
Additional service fee may apply.
    Wonderful! 4.8/5
    (81 reviews)
    avg/night
    • 2 BR
    • 2 BA
    • Sleeps 5
    Apartment #3920062
    81
    Viewed 137 times in the last 48 hours
      Wonderful! 4.9/5
      (32 reviews)
      avg/night
      • 2 BR
      • 2 BA
      • Sleeps 5
      Apartment #4025774
      32
      Viewed 12 times in the last 48 hours
        Excellent! 4.7/5
        (27 reviews)
        avg/night
        • 3 BR
        • 2 BA
        • Separate Toilet
        • Sleeps 7
        Apartment #4055099
        27
        Viewed 18 times in the last 48 hours
          Wonderful! 4.8/5
          (13 reviews)
          avg/night
          • 1 BR
          • 1 BA
          • Sleeps 2
          Cottage #3926632
          13
          Viewed 5 times in the last 48 hours
            Wonderful! 4.9/5
            (54 reviews)
            avg/night
            • 2 BR
            • 2 BA
            • Sleeps 5
            Apartment #3960471
            54
            Viewed 27 times in the last 48 hours
              Wonderful! 4.8/5
              (19 reviews)
              avg/night
              • 2 BR
              • 2 BA
              • Sleeps 6
              Yacht #3962573
              19
              Viewed 44 times in the last 48 hours
                Wonderful! 4.9/5
                (54 reviews)
                avg/night
                • 2 BR
                • 1 BA
                • Separate Toilet
                • Sleeps 6
                Condo #3893669
                54
                Viewed 382 times in the last 48 hours
                  Wonderful! 4.9/5
                  (34 reviews)
                  avg/night
                  • 2 BR
                  • 2 BA
                  • Sleeps 5
                  Apartment #3970888
                  34
                  Viewed 44 times in the last 48 hours
                    Exceptional! 5.0/5
                    (8 reviews)
                    avg/night
                    • 1 BR
                    • 1 BA
                    • Sleeps 4
                    Apartment #4069856
                    8
                    Viewed 8 times in the last 48 hours
                      Wonderful! 4.8/5
                      (13 reviews)
                      avg/night
                      • 1 BR
                      • 1 BA
                      • Sleeps 4
                      Cottage #3736260
                      13
                      Viewed 9 times in the last 48 hours
                        Wonderful! 4.9/5
                        (35 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Sleeps 7
                        Apartment #3960472
                        35
                        Viewed 53 times in the last 48 hours
                          Exceptional! 5.0/5
                          (47 reviews)
                          avg/night
                          • 2 BR
                          • 1 BA
                          • Sleeps 6
                          Apartment #3928905
                          47
                          Viewed 17 times in the last 48 hours
                            Wonderful! 4.8/5
                            (47 reviews)
                            avg/night
                            • 2 BR
                            • 1 BA
                            • Sleeps 6
                            Apartment #3661758
                            47
                            Viewed 28 times in the last 48 hours
                              Exceptional! 5.0/5
                              (14 reviews)
                              avg/night
                              • 2 BR
                              • 1 BA
                              • Sleeps 5
                              Cottage #564192vb
                              14
                              Viewed 18 times in the last 48 hours
                                Exceptional! 5.0/5
                                (42 reviews)
                                avg/night
                                • 2 BR
                                • 1 BA
                                • Sleeps 6
                                Cottage #512709vb
                                42
                                Viewed 14 times in the last 48 hours
                                  Excellent! 4.6/5
                                  (39 reviews)
                                  avg/night
                                  • 3 BR
                                  • 3 BA
                                  • Sleeps 6
                                  House #792735vb
                                  39
                                  Viewed 25 times in the last 48 hours
                                    Exceptional! 5.0/5
                                    (12 reviews)
                                    avg/night
                                    • 6 BR
                                    • 5 BA
                                    • Sleeps 20
                                    Estate #4258796
                                    12
                                    Viewed 127 times in the last 48 hours
                                      Excellent! 4.7/5
                                      (22 reviews)
                                      avg/night
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 5
                                      Apartment #4096548
                                      22
                                      Viewed 15 times in the last 48 hours
                                        Excellent! 4.6/5
                                        (47 reviews)
                                        avg/night
                                        • 1 BR
                                        • 1 BA
                                        • Sleeps 4
                                        Condo #386075
                                        47
                                        Viewed 15 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (17 reviews)
                                          avg/night
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 4
                                          Apartment #181404
                                          17
                                          Viewed 5 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (55 reviews)
                                            avg/night
                                            • 1 BR
                                            • 1 BA
                                            • Separate Toilet
                                            • Sleeps 2
                                            House #443453vb
                                            55
                                            Viewed 24 times in the last 48 hours
                                              Wonderful! 4.8/5
                                              (33 reviews)
                                              avg/night
                                              • 2 BR
                                              • 1 BA
                                              • Sleeps 5
                                              Cottage #176726
                                              33
                                              Viewed 8 times in the last 48 hours
                                                Excellent! 4.5/5
                                                (11 reviews)
                                                avg/night
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 5
                                                Apartment #4105862
                                                11
                                                Viewed 26 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (33 reviews)
                                                  avg/night
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  House #367873
                                                  33
                                                  Viewed 39 times in the last 48 hours
                                                    Wonderful! 4.9/5
                                                    (61 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 5
                                                    Townhome #247506vb
                                                    61
                                                    Viewed 29 times in the last 48 hours
                                                      Excellent! 4.6/5
                                                      (32 reviews)
                                                      avg/night
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 4
                                                      Cottage #592845vb
                                                      32
                                                      Viewed 13 times in the last 48 hours
                                                        Excellent! 4.7/5
                                                        (21 reviews)
                                                        avg/night
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 6
                                                        Apartment #4108939
                                                        21
                                                        Viewed 39 times in the last 48 hours
                                                          Wonderful! 4.8/5
                                                          (25 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          Apartment #3968741
                                                          25
                                                          Viewed 25 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (87 reviews)
                                                            avg/night
                                                            • 3 BR
                                                            • 1 BA
                                                            • Sleeps 8
                                                            Apartment #286323
                                                            87
                                                            Viewed 8 times in the last 48 hours
                                                              Wonderful! 4.8/5
                                                              (25 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 1 BA
                                                              • Sleeps 8
                                                              Cottage #3004281
                                                              25
                                                              Viewed 15 times in the last 48 hours
                                                                Wonderful! 4.8/5
                                                                (39 reviews)
                                                                avg/night
                                                                • 1 BR
                                                                • 1 BA
                                                                • Sleeps 2
                                                                Apartment #739050vb
                                                                39
                                                                Viewed 24 times in the last 48 hours
                                                                  Wonderful! 4.8/5
                                                                  (26 reviews)
                                                                  avg/night
                                                                  • 4 BR
                                                                  • 2 BA
                                                                  • Separate Toilet
                                                                  • Sleeps 10
                                                                  House #554204vb
                                                                  26
                                                                  Viewed 39 times in the last 48 hours
                                                                    Wonderful! 4.8/5
                                                                    (23 reviews)
                                                                    avg/night
                                                                    • Studio
                                                                    • 1 BA
                                                                    • Sleeps 2
                                                                    Studio #605387vb
                                                                    23
                                                                    Viewed 17 times in the last 48 hours
                                                                      Exceptional! 5.0/5
                                                                      (15 reviews)
                                                                      avg/night
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      Apartment #609643vb
                                                                      15
                                                                      Viewed 16 times in the last 48 hours
                                                                        • 5 BR
                                                                        • 2 BA
                                                                        • Sleeps 12
                                                                        House #3895901
                                                                        28
                                                                        Viewed 30 times in the last 48 hours
                                                                          Excellent! 4.6/5
                                                                          (28 reviews)
                                                                          avg/night
                                                                          • 4 BR
                                                                          • 2 BA
                                                                          • Sleeps 8
                                                                          Apartment #3944808
                                                                          28
                                                                          Viewed 10 times in the last 48 hours
                                                                            Wonderful! 4.9/5
                                                                            (9 reviews)
                                                                            avg/night
                                                                            • 1 BR
                                                                            • 1 BA
                                                                            • Sleeps 5
                                                                            Cottage #750340vb
                                                                            9
                                                                            Viewed 5 times in the last 48 hours
                                                                              Wonderful! 4.9/5
                                                                              (106 reviews)
                                                                              avg/night
                                                                              • 1 BR
                                                                              • 1 BA
                                                                              • Sleeps 4
                                                                              Condo #395506
                                                                              106
                                                                              Viewed 25 times in the last 48 hours
                                                                                Wonderful! 4.9/5
                                                                                (99 reviews)
                                                                                avg/night
                                                                                • 3 BR
                                                                                • 1 BA
                                                                                • Sleeps 5
                                                                                Condo #367114
                                                                                99
                                                                                Viewed 29 times in the last 48 hours
                                                                                  Exceptional! 5.0/5
                                                                                  (13 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 3 BA
                                                                                  • Sleeps 8
                                                                                  House #714244vb
                                                                                  13
                                                                                  Viewed 17 times in the last 48 hours
                                                                                    Wonderful! 4.9/5
                                                                                    (14 reviews)
                                                                                    avg/night
                                                                                    • 4 BR
                                                                                    • 2 BA
                                                                                    • Separate Toilet
                                                                                    • Sleeps 8
                                                                                    Apartment #3979912
                                                                                    14
                                                                                    Viewed 18 times in the last 48 hours
                                                                                      Excellent! 4.7/5
                                                                                      (19 reviews)
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 5
                                                                                      Apartment #132084
                                                                                      19
                                                                                      Viewed 24 times in the last 48 hours
                                                                                        Wonderful! 4.8/5
                                                                                        (41 reviews)
                                                                                        avg/night
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        Condo #685891vb
                                                                                        41
                                                                                        Viewed 15 times in the last 48 hours
                                                                                          Wonderful! 4.9/5
                                                                                          (16 reviews)
                                                                                          avg/night
                                                                                          • 3 BR
                                                                                          • 1 BA
                                                                                          • Separate Toilet
                                                                                          • Sleeps 6
                                                                                          House #4034861
                                                                                          16
                                                                                          Viewed 15 times in the last 48 hours
                                                                                            Wonderful! 4.9/5
                                                                                            (36 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 3
                                                                                            Condo #111553
                                                                                            36
                                                                                            Viewed 16 times in the last 48 hours
                                                                                              Excellent! 4.6/5
                                                                                              (43 reviews)
                                                                                              avg/night
                                                                                              • 1 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 4
                                                                                              Apartment #3836908
                                                                                              43
                                                                                              Viewed 22 times in the last 48 hours
                                                                                                Exceptional! 5.0/5
                                                                                                (23 reviews)
                                                                                                avg/night
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 2
                                                                                                Apartment #561483vb
                                                                                                23
                                                                                                Viewed 7 times in the last 48 hours
                                                                                                  Wonderful! 4.9/5
                                                                                                  (50 reviews)
                                                                                                  avg/night
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  Condo #3849683
                                                                                                  50
                                                                                                  Viewed 29 times in the last 48 hours
                                                                                                    Exceptional! 5.0/5
                                                                                                    (45 reviews)
                                                                                                    avg/night
                                                                                                    • 4 BR
                                                                                                    • 5 BA
                                                                                                    • Separate Toilet
                                                                                                    • Sleeps 11
                                                                                                    House #122422
                                                                                                    45
                                                                                                    Viewed 81 times in the last 48 hours
                                                                                                      Wonderful! 4.8/5
                                                                                                      (58 reviews)
                                                                                                      avg/night
                                                                                                      • 4 BR
                                                                                                      • 2 BA
                                                                                                      • Separate Toilet
                                                                                                      • Sleeps 8
                                                                                                      House #82301vb
                                                                                                      58
                                                                                                      Viewed 18 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      the best apartment ever

                                                                                                      5 of 5
                                                                                                      We stayed a little way out of Boston in Ashmont ant the location of the flat was perfect. It was close to the 'T' and the small town where you could have a lovely meal and do the shopping basics. We did not hire a car as we have done in previous visits to the US and found that we did not need one. If we could not get the T or a bus then we used Uber which was a simple and quick way to get a taxi. The flat itself was wonderful. Clean and with everything that you could need and plenty large enough for me and my husband and would have been big enough for a family.
                                                                                                      • Review Submitted: 28-Nov-2016
                                                                                                      • Date of Stay: Nov 2016

                                                                                                      🙂

                                                                                                      5 of 5
                                                                                                      House was brilliant. Perfect location. Ideal base for visiting Salem and Boston. Marblehead is a beautiful town. Lovely quiet street. Plenty of amenities. Grocery shop just along the road a bit. Maria is very kind and helpful. No complaints 🙂
                                                                                                      • Review Submitted: 14-Nov-2016
                                                                                                      • Date of Stay: Oct 2016

                                                                                                      Perfect location and beautiful flat.

                                                                                                      5 of 5
                                                                                                      We were attending a wedding at the Charles River museum and the location of the apartment was ideal. The flat is very well equipped and the bedrooms are spacious and comfortable. The commuter train station for Boston is very convenient and you are in the city within 20 minutes. We never met Mark but he always answered emails straightaway and tried to accommodate all our requests. Would definitely recommend this apartment.
                                                                                                      • Review Submitted: 24-Oct-2016
                                                                                                      • Date of Stay: Oct 2016