Discover a selection of 141 vacation rentals in Winchester, NH that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and outdoor grills and BBQs. Prices start at $121 per night, and houses and condos are popular options for a stay in Winchester. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Winchester
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Destination guide

Why people love visiting tranquil Winchester

The lake and forests provide a pleasant backdrop to your vacation home in Winchester. This city's canoeing, boating and kayaking attract many visitors, and its relaxing and scenic location add to the charm. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities

Activities and attractions in Winchester

Are you hoping to discover attractions to visit while you're in the area? Venture out of your cozy vacation rental and experience everything that makes Winchester a one-of-a-kind vacation spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Madame Sherri Forest (9.3 mi / 15 km)
  • Chesterfield Gorge Natural Area (9.8 mi / 15.7 km)
  • Rhododendron State Park (9.9 mi / 15.9 km)
  • Brattleboro Country Club (12.2 mi / 19.6 km)
  • Brentwood Golf Course (14.9 mi / 23.9 km)
  • Monadnock State Park (15.8 mi / 25.4 km)
Natural features

Exploring the natural landscape of Winchester

Whether you're an active traveler or just want to appreciate the scenery, Winchester is a great place to get outside. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Madame Sherri Forest (9.3 mi / 15 km)
  • Chesterfield Gorge Natural Area (9.8 mi / 15.7 km)
  • Rhododendron State Park (9.9 mi / 15.9 km)
  • Fort Dummer State Park (10 mi / 16 km)
  • Wantastiquet Mountain (10 mi / 16.1 km)
  • Brattleboro Common (10.7 mi / 17.2 km)

How many vacation rentals are available around Winchester, NH?

Our 2021 property listings offer a large selection of 141 vacation rentals around Winchester. From 96 house rentals to 26 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Winchester?

Yes, of course. Vrbo has 96 Houses in Winchester. Our other popular types of vacation rentals in Winchester include:

  • Condos/Apartments: 26 rentals available
  • Cabins: 24 rentals available
  • Cottages: 24 rentals available

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

Can I find a vacation rental with pool in Winchester?

Yes, you can select your preferred vacation rental with pool among our 15 vacation rentals with pool available in Winchester. Please use our search bar to access the selection of vacation rentals available.