Where to stay around Winchester?

Our 2018 accommodation listings offer a large selection of 1,374 holiday lettings near Winchester. From 933 apartments to 196 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: 518 holiday homes
  • Jamaica Plain: 157 holiday homes
  • Beacon Hill: 387 holiday homes
  • North End: 329 holiday homes
  • Central-Maverick Square / Paris Street: 83 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: 1,633 holiday lettings
  • Winchester Station: 1,627 holiday lettings
  • New England Aquarium: 1,631 holiday lettings
  • Cambridgeside Galleria: 1,614 holiday lettings
  • Salem Pioneer Village 1630: 1,934 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 933 apartments in Winchester. Our other popular types of Winchester holiday rentals include:

  • Condos: 196 self catering accommodations
  • Houses: 146 self catering accommodations
  • Boats: 8 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 88 holiday homes with pool available in Winchester. Please use our search bar to access the selection of holiday rentals available.

    Take in the lake beauty of Winchester

    The lakes, flowers and wildlife display a scene truly unique to Winchester. This family-friendly city attracts visitors thanks to its football and bird watching. Top attractions in the area include Harvard Square, USS Constitution Museum and TD Garden. Whether you're planning a family holiday, a trip with friends or a romantic retreat, consider a rental home. Many rentals come with a full kitchen and separate dining area.

    Attractions in and around Winchester

    Looking for places to see while you're in Winchester? Take the children and visit New England Aquarium, Artisans Asylum and Franklin Park Zoo. Visitors searching for nearby cultural experiences can take a trip to Harvard Square and Bunker Hill Monument, or spend an enlightening afternoon at USS Constitution Museum or Boston Museum of Fine Arts. To appreciate the outdoor scene, make time for beaches such as Revere Beach and Wollaston Beach, and green spaces such as Boston Public Garden and Boston Common. You can take a shopping trip to Faneuil Hall Marketplace, Copley Place and Burlington Mall. Plan to attend a game or event? Get tickets for TD Garden or Fenway Park. You might also want to add other must-see places in the region such as Hynes Convention Center, Boston Convention and Exhibition Center or Semitic Museum to your agenda.