Find the best place to stay — Winchester

Where to stay around Winchester?

Our 2018 property listings offer a large selection of 50 vacation rentals near Winchester. From 19 houses to 11 cottages, 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 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:

  • United States Navy Seabee Bridge: 454 vacation rentals
  • Spofford Lake: 116 vacation rentals
  • Mount Wachusett Community College: 43 vacation rentals
  • Monadnock State Park: 91 vacation rentals
  • Vermont Jazz Center: 358 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 houses in Winchester?

Yes, of course. HomeAway has 19 houses in Winchester. Our other popular types of vacation rentals in Winchester include:

  • Cottages: 11 rentals available
  • Apartments: 9 rentals available
  • Cabins: 4 rentals available

Can I rent skiing rentals in Winchester?

Absolutely, HomeAway has 24 skiing rentals in Winchester. You have also many other possibilities in Winchester area, including:

  • Golf rentals: 22 rentals
  • Waterfront rentals: 17 rentals
  • Lake rentals: 16 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 3 vacation rentals with pool available in Winchester. Please use our search bar to access the selection of vacation rentals available.

    Choose a Vacation Rental for Your Winchester Getaway

    Learn about the unique charm of Winchester with a stay in a vacation home rental. This city has something for everyone. 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? Enjoy a visit to Schell Bridge, Asbury United Methodist Church and Madame Sherri Forest during your stay. Also a trip to Madame Sherris Castle Ruins, Guilford Welcome Center or Vermont Jazz Center might be a nice excursion.