Winchester, MA, USA

Winchester, MA, USA

We found 1,387 holiday rentals — enter your dates for availability

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Find the best place to stay — Winchester

Where to stay around Winchester?

Our 2018 accommodation listings offer a large selection of 1,387 holiday lettings near Winchester. From 924 apartments to 213 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: 534 holiday homes
  • Jamaica Plain: 171 holiday homes
  • Beacon Hill: 385 holiday homes
  • North End: 317 holiday homes
  • Central-Maverick Square / Paris Street: 69 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 travelers, the most popular points of interest to stay near are:

  • Winchester Wedgemere Station: 1,605 holiday lettings
  • Winchester Station: 1,609 holiday lettings
  • New England Aquarium: 1,645 holiday lettings
  • Cambridgeside Galleria: 1,651 holiday lettings
  • Salem Pioneer Village 1630: 1,952 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 924 apartments in Winchester. Our other popular types of Winchester holiday rentals include:

  • Condos: 213 self catering accommodations
  • Houses: 156 self catering accommodations
  • Boats: 7 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 105 holiday homes with pool available in Winchester. Please use our search bar to access the selection of holiday rentals available.