Find the best place to stay — Winchester

Where to stay around Winchester?

Our 2018 property listings offer a large selection of 1,468 vacation rentals near Winchester. From 930 apartments to 207 condos, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Winchester for a holiday or a weekend are on HomeAway.

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

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Winchester:

  • Back Bay: 535 vacation rentals
  • Downtown: 621 vacation rentals
  • Beacon Hill: 392 vacation rentals
  • North End: 322 vacation rentals
  • South End: 537 vacation rentals

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

What are the popular points of interest near where I can stay when traveling to Winchester?

HomeAway offers a large selection of vacation rentals near lovely places in Winchester. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Winchester Wedgemere Station: 1,767 vacation rentals
  • Winchester Station: 1,765 vacation rentals
  • Boston Common: 1,794 vacation rentals
  • Fenway Park: 1,770 vacation rentals
  • Boston Convention and Exhibition Center: 1,796 vacation rentals

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 vacation rentals available near the point of interest of your choice.

Can I rent apartments in Winchester?

Yes, of course. HomeAway has 930 apartments in Winchester. Our other popular types of vacation rentals in Winchester include:

  • Condos: 207 rentals available
  • Houses: 142 rentals available
  • Studios: 33 rentals available

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

Can I rent downtown rentals in Winchester?

Absolutely, HomeAway has 291 downtown rentals in Winchester. You have also many other possibilities in Winchester area, including:

  • Golf rentals: 128 rentals
  • Near the ocean rentals: 90 rentals
  • Skiing rentals: 77 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with pool in Winchester?

Yes, you can select your preferred vacation rental with pool among our 92 vacation rentals with pool available in Winchester. Please use our search bar to access the selection of vacation rentals available.

    Take in the Lakeside Beauty of Winchester

    The lake, flowers and wildlife display a scene truly unique to Winchester. This family-friendly city allures visitors with its soccer and bird watching. Top attractions in the area include Harvard Square, USS Constitution Museum and TD Garden. Whether you're planning a family vacation, friends trip or 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 kids and check out 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 like 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 like Hynes Convention Center, Boston Convention and Exhibition Center or Semitic Museum to your agenda.