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.
Verified Review icon 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 pet-dog svg-multiunit

Make a self catering cottage or holiday rental in Bolsover, Derbyshire your home away from home

Nestled amidst the pretty Derbyshire countryside, a holiday home in Bolsover makes the ideal base for exploring the area. Chesterfield is just 7 miles away and Chatsworth House, Kedleston Hall and many other attractions are close by. Bolsover actually dates back over 1000 years as it was recorded in the Domesday Book in 1086 as the property of William Peverel, a knight who fought at the Battle of Hastings. The Peverel family built Bolsover Castle in the 12th century, more as an impressive home than a defensive structure. Bolsover was once a thriving mining town and many of the homes were built for mining families. It has plenty of local shops, pubs and cafés along the pedestrianised High Street along with the local Church of St Mary.

Things to Do in Bolsover, Derbyshire Walking and Hiking

Bolsover is on the edge of the Peak District, known for its excellent walking opportunites and scenic beauty. Hiking, hill walking and mountain biking can all be enjoyed in the area and the small picturesque villages such as Bakewell make great stopping places for refreshments along the way.

Explore the Town

Bolsover town is worth exploring on foot. At the end of the High Street, with its bustling local trade, is St Mary's church which has interesting monuments of the Cavendish family who later owned and rebuilt the castle. The tomb of Charles Cavendish and his wife are worth particular attention. The town also has a memorial cross and the Hudson Bay pub has an interesting history.

Places to Visit Near Bolsover, Derbyshire Cresswell Crags

Cresswell Crags are set in a limestone gorge which is honeycombed with caves and crevices dating back to the Ice Age. This unique site is the only known example of Palaeolithic cave art in Britain and the caves are world-famous.

Bolsover Castle

The 12th century superbly maintained Bolsover Castle offers an interesting visit with elaborate fireplaces, panelled rooms and ornate wall paintings. An audio guide is available telling the life of the owners and the history of the castle itself. The Venus Garden has a restored fountain with 23 statues and the original Riding School can also be seen.

Chatsworth House and Gardens

Home to the Duke and Duchess of Devonshire, the grand stately home of Chatsworth is one of the wonders of the Peak District. Built in 1688, a tour of the house will reveal a Great Staircase, magnificent painted ceilings, fine furnishings, sculptures and artworks. The gardens were planted by Capability Brown and there is also a farmyard, garden centre, deer park and an adventure playground.

Weather in Bolsover, Derbyshire

The Bolsover area has mild winters rarely dropping below freezing, and warm summers. Temperatures in August average 21°C (70°F) and the area has moderate rainfall and some cloudy days throughout the year.

Travel to Bolsover, Derbyshire

The nearest airport to your holiday home in Bolsover is the East Midlands (EMA) Airport which is 36 miles (56km) away. Manchester Airport and the Leeds Bradford Airport are also less than 50 miles (80km) drive away. Trains frequently run to the nearby cities of Derby and Nottingham. Alternatively, consider driving to your Derbyshire holiday home which is just a few miles from the M1.

  View Map Map
  • Showing 1-50 of 300+
Additional service fee may apply.
    • 3 BR
    • Separate Toilets
    • Sleeps 5
    Cottage #1895066
      • 1 BR
      • 1 BA
      • Sleeps 2
      Cottage #1964936
        • 1 BR
        • 1 BA
        • Sleeps 2
        Cottage #6897923
          Excellent! 4.7/5
          (26 reviews)
          avg/night
          • 2 BR
          • 1 BA
          • Sleeps 4
          Bungalow #1944062
          26
          Viewed 46 times in the last 48 hours
            Exceptional! 5/5
            (13 reviews)
            avg/night
            • 3 BR
            • 1 BA
            • Separate Toilet
            • Sleeps 5
            Cottage #6065995
            13
            Viewed 58 times in the last 48 hours
              Excellent! 4.7/5
              (15 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • Sleeps 8
              Cottage #1845548
              15
              Viewed 72 times in the last 48 hours
                Excellent! 4.4/5
                (13 reviews)
                avg/night
                • 2 BR
                • 1 BA
                • Sleeps 5
                Cottage #6570111
                13
                Viewed 48 times in the last 48 hours
                  Exceptional! 5/5
                  (24 reviews)
                  avg/night
                  • 4 BR
                  • 2 BA
                  • Separate Toilet
                  • Sleeps 9
                  Cottage #1769753
                  24
                  Viewed 52 times in the last 48 hours
                    Wonderful! 4.9/5
                    (12 reviews)
                    avg/night
                    • 3 BR
                    • 1 BA
                    • Sleeps 5
                    Cottage #6735582
                    12
                    Viewed 25 times in the last 48 hours
                      Very Good! 4.1/5
                      (22 reviews)
                      avg/night
                      • 4 BR
                      • 3 BA
                      • Sleeps 9
                      Barn #402484
                      22
                      Viewed 96 times in the last 48 hours
                        Excellent! 4.5/5
                        (4 reviews)
                        avg/night
                        • 2 BR
                        • 1 BA
                        • Separate Toilet
                        • Sleeps 4
                        Cottage #8077099
                        4
                        Viewed 24 times in the last 48 hours
                          Exceptional! 5/5
                          (8 reviews)
                          avg/night
                          • 4 BR
                          • 3 BA
                          • Separate Toilet
                          • Sleeps 8
                          Cottage #8148892
                          8
                          Viewed 45 times in the last 48 hours
                            Wonderful! 4.8/5
                            (32 reviews)
                            avg/night
                            • 1 BR
                            • 1 BA
                            • Sleeps 2
                            Cottage #8117637
                            32
                            Viewed 45 times in the last 48 hours
                              Wonderful! 4.9/5
                              (8 reviews)
                              avg/night
                              • 2 BR
                              • 1 BA
                              • Sleeps 5
                              Cottage #6581460
                              8
                              Viewed 10 times in the last 48 hours
                                Excellent! 4.6/5
                                (25 reviews)
                                avg/night
                                • 2 BR
                                • 2 BA
                                • Sleeps 4
                                Cottage #8093007
                                25
                                Viewed 55 times in the last 48 hours
                                  Wonderful! 4.8/5
                                  (13 reviews)
                                  avg/night
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 8
                                  House #8113023
                                  13
                                  Viewed 15 times in the last 48 hours
                                    Wonderful! 4.8/5
                                    (4 reviews)
                                    avg/night
                                    • 4 BR
                                    • 2 BA
                                    • Separate Toilet
                                    • Sleeps 8
                                    Cottage #6856539
                                    4
                                    Viewed 59 times in the last 48 hours
                                      Wonderful! 4.8/5
                                      (25 reviews)
                                      avg/night
                                      • 2 BR
                                      • 1 BA
                                      • Sleeps 3
                                      Cottage #1860724
                                      25
                                      Viewed 32 times in the last 48 hours
                                        Wonderful! 4.9/5
                                        (12 reviews)
                                        avg/night
                                        • 2 BR
                                        • 2 BA
                                        • Sleeps 4
                                        Cottage #8143122
                                        12
                                        Viewed 21 times in the last 48 hours
                                          Wonderful! 4.8/5
                                          (5 reviews)
                                          avg/night
                                          • 1 BR
                                          • 1 BA
                                          • Sleeps 2
                                          Cottage #8158011
                                          5
                                          Viewed 8 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (34 reviews)
                                            avg/night
                                            • 4 BR
                                            • 4 BA
                                            • Sleeps 12
                                            Multiple rentals House #1011814
                                            34
                                            Viewed 38 times in the last 48 hours
                                              Wonderful! 4.8/5
                                              (6 reviews)
                                              avg/night
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 4
                                              Barn #6007285
                                              6
                                              Viewed 10 times in the last 48 hours
                                                Wonderful! 4.8/5
                                                (12 reviews)
                                                avg/night
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 4
                                                Bungalow #8158012
                                                12
                                                Viewed 15 times in the last 48 hours
                                                  Exceptional! 5/5
                                                  (19 reviews)
                                                  avg/night
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  Cottage #8164942
                                                  19
                                                  Viewed 9 times in the last 48 hours
                                                    Wonderful! 4.9/5
                                                    (28 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 1 BA
                                                    • Separate Toilet
                                                    • Sleeps 4
                                                    Cottage #8170344
                                                    28
                                                    Viewed 29 times in the last 48 hours
                                                      • 3 BR
                                                      • 1 BA
                                                      • Sleeps 6
                                                      Multiple rentals Cottage #6788213
                                                      2
                                                      Viewed 32 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (36 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 3 BA
                                                        • Sleeps 10
                                                        Bungalow #1731448
                                                        36
                                                        Viewed 30 times in the last 48 hours
                                                          Wonderful! 4.8/5
                                                          (6 reviews)
                                                          avg/night
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 2
                                                          Apartment #6117030
                                                          6
                                                          Viewed 40 times in the last 48 hours
                                                            Wonderful! 4.8/5
                                                            (11 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 4
                                                            Cottage #8088401
                                                            11
                                                            Viewed 22 times in the last 48 hours
                                                              Wonderful! 4.8/5
                                                              (4 reviews)
                                                              avg/night
                                                              • 2 BR
                                                              • 3 BA
                                                              • Sleeps 6
                                                              Cottage #6556132
                                                              4
                                                              Viewed 15 times in the last 48 hours
                                                                Wonderful! 4.8/5
                                                                (35 reviews)
                                                                avg/night
                                                                • 5 BR
                                                                • 2 BA
                                                                • Sleeps 14
                                                                Multiple rentals Farmhouse #899651
                                                                35
                                                                Viewed 19 times in the last 48 hours
                                                                  Wonderful! 4.8/5
                                                                  (16 reviews)
                                                                  avg/night
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 5
                                                                  Bungalow #8171467
                                                                  16
                                                                  Viewed 15 times in the last 48 hours
                                                                    Wonderful! 4.9/5
                                                                    (24 reviews)
                                                                    avg/night
                                                                    • 9 BR
                                                                    • 9 BA
                                                                    • Sleeps 24
                                                                    Multiple rentals Barn #1767414
                                                                    24
                                                                    Viewed 62 times in the last 48 hours
                                                                      Exceptional! 5/5
                                                                      (9 reviews)
                                                                      avg/night
                                                                      • 2 BR
                                                                      • 1 BA
                                                                      • Sleeps 4
                                                                      Multiple rentals Cottage #6788213
                                                                      9
                                                                      Viewed 18 times in the last 48 hours
                                                                        Wonderful! 4.9/5
                                                                        (26 reviews)
                                                                        avg/night
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • Separate Toilet
                                                                        • Sleeps 4
                                                                        Cottage #8128098
                                                                        26
                                                                        Viewed 20 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (19 reviews)
                                                                          avg/night
                                                                          • 4 BR
                                                                          • 2 BA
                                                                          • Separate Toilet
                                                                          • Sleeps 8
                                                                          House #8149683
                                                                          19
                                                                          Viewed 12 times in the last 48 hours
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 5
                                                                            Cottage #6019583
                                                                            3
                                                                            Viewed 40 times in the last 48 hours
                                                                              Excellent! 4.7/5
                                                                              (13 reviews)
                                                                              avg/night
                                                                              • 5 BR
                                                                              • 3 BA
                                                                              • Separate Toilet
                                                                              • Sleeps 14
                                                                              Farmhouse #8075767
                                                                              13
                                                                              Viewed 46 times in the last 48 hours
                                                                                Wonderful! 4.9/5
                                                                                (12 reviews)
                                                                                avg/night
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 2
                                                                                Cottage #8143330
                                                                                12
                                                                                Viewed 27 times in the last 48 hours
                                                                                  Wonderful! 4.8/5
                                                                                  (13 reviews)
                                                                                  avg/night
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  Barn #8137619
                                                                                  13
                                                                                  Viewed 38 times in the last 48 hours
                                                                                    Excellent! 4.4/5
                                                                                    (9 reviews)
                                                                                    avg/night
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    Cottage #8173489
                                                                                    9
                                                                                    Viewed 22 times in the last 48 hours
                                                                                      Wonderful! 4.8/5
                                                                                      (9 reviews)
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 6
                                                                                      Cottage #1887405
                                                                                      9
                                                                                      Viewed 44 times in the last 48 hours
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        Cottage #6551168
                                                                                        Viewed 10 times in the last 48 hours
                                                                                          Exceptional! 5/5
                                                                                          (4 reviews)
                                                                                          avg/night
                                                                                          • 3 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 6
                                                                                          Multiple rentals Cottage #6788213
                                                                                          4
                                                                                          Viewed 42 times in the last 48 hours
                                                                                            Excellent! 4.3/5
                                                                                            (9 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 5
                                                                                            Cottage #8149314
                                                                                            9
                                                                                            Viewed 16 times in the last 48 hours
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 4
                                                                                              Cottage #6924840
                                                                                              1
                                                                                              Viewed 65 times in the last 48 hours
                                                                                                Exceptional! 5/5
                                                                                                (5 reviews)
                                                                                                avg/night
                                                                                                • 2 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 4
                                                                                                Cottage #6541198
                                                                                                5
                                                                                                Viewed 13 times in the last 48 hours
                                                                                                  • 4 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 8
                                                                                                  House #8112385
                                                                                                  2
                                                                                                  Viewed 17 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (27 reviews)
                                                                                                    avg/night
                                                                                                    • 6 BR
                                                                                                    • 4 BA
                                                                                                    • Sleeps 16
                                                                                                    Multiple rentals Barn #1767414
                                                                                                    27
                                                                                                    Viewed 45 times in the last 48 hours
                                                                                                      Excellent! 4.7/5
                                                                                                      (7 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 4
                                                                                                      Multiple rentals Cottage #6788213
                                                                                                      7
                                                                                                      Viewed 34 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      A lovely bolthole close to good pubs

                                                                                                      5 of 5
                                                                                                      We love this cottage. It's beautifully decorated, well equipped, clean and a real home from home. You get privacy but a warm welcome. In nearby Ashover - under 2 miles away - there are great pubs and ales. You can walk there from the cottage. There is lots of room for two people but two couples could stay here as well - both rooms have ensuites. A busy bird feeder is just outside. We've seen everything from nuthatches to goldfinches coming and going. I couldn't fault this lovely place and will definitely be back.
                                                                                                      • Review Submitted: 27-Feb-2017
                                                                                                      • Date of Stay: Feb 2017

                                                                                                      Immaculate and comfortable property ,everything we hoped it would be well located will return

                                                                                                      5 of 5
                                                                                                      On the edge of the beautiful village of Ashton on the Water and less than 3/4 mile from Monsal Head the property is perfect for a walking trip. The house itself was stunning clean and well equipped. A really well converted stable. The house file pointed us to some beautiful walk and George thanks for sending us to The Manners in Bakewell great lunch.
                                                                                                      • Review Submitted: 26-Feb-2017
                                                                                                      • Date of Stay: Feb 2017

                                                                                                      Lovely setting - great property

                                                                                                      5 of 5
                                                                                                      All clean and fresh inside. Comfortable beds. Lovely games room. WiFi not available in each property if that's what you needed. Just in games room. Otherwise great.
                                                                                                      • Review Submitted: 24-Feb-2017
                                                                                                      • Date of Stay: Feb 2017