Where to stay around Winchester?

Our 2018 accommodation listings offer a large selection of 1,437 holiday lettings near Winchester. From 955 apartments to 231 condos, find unique self catering accommodation for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay near Winchester is on HomeAway.

What is the best area to stay when travelling to Winchester?

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday accommodations for a long holiday or just a weekend break in Winchester:

  • Back Bay: 553 holiday homes
  • Jamaica Plain: 162 holiday homes
  • Beacon Hill: 416 holiday homes
  • Dorchester: 146 holiday homes
  • North End: 360 holiday homes

For other neighbourhoods, please use our search bar to access the selection of holiday rentals available.

What are the most popular points of interest and landmarks to stay near when travelling to Winchester?

HomeAway offers a large selection of holiday accommodations near great places in Winchester. From HomeAway travellers, the most popular points of interest to stay near are:

  • Winchester Wedgemere Station: 1,686 holiday lettings
  • Winchester Station: 1,683 holiday lettings
  • New England Aquarium: 1,711 holiday lettings
  • Cambridgeside Galleria: 1,704 holiday lettings
  • Salem Pioneer Village 1630: 2,009 holiday lettings

But there are many other points of interest around Winchester listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent apartments in Winchester?

Yes, of course. HomeAway offers 955 apartments in Winchester. Our other popular types of Winchester holiday rentals include:

  • Condos: 231 self catering accommodations
  • Houses: 153 self catering accommodations
  • Boats: 6 self catering accommodations

But you can also enjoy a great stay in one of our other holiday rentals including cottages and more.

Can I find a holiday accommodation with pool in Winchester?

Yes, you can select your preferred holiday accommodation with pool among our 98 holiday homes with pool available in Winchester. Please use our search bar to access the selection of holiday rentals available.

    The lakeside setting of Winchester is ready to explore

    The wildlife and lake provide a pleasant backdrop to your holiday home in Winchester. This city is well-known for its football matches and bird watching. Harvard Square and USS Constitution Museum are just a couple of the must-see attractions in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

    Activities and attractions in and around Winchester

    Are you hoping to find top things to see and do while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Winchester a fun spot to go on holiday. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

    • New England Aquarium (8.1 mi / 13 km)
    • Artisans Asylum (5.3 mi / 8.6 km)
    • Franklin Park Zoo (10.8 mi / 17.3 km)
    • Andover Bird Sanctuary (13.7 mi / 22 km)
    • Salem Toy Museum (13.8 mi / 22.2 km)
    • Salem Willows Park (15.2 mi / 24.4 km)

    Exploring the natural features in Winchester

    Whether you're an adventurous traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Winchester. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

    • Boston Public Garden (7.8 mi / 12.6 km)
    • Boston Common (7.9 mi / 12.7 km)
    • Walden Pond (10 mi / 16.1 km)
    • Royall Park (3.3 mi / 5.4 km)
    • Logan Park (3.5 mi / 5.7 km)
    • Magoun Park (3.5 mi / 5.7 km)