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)

Can I find a vacation rental around Winchester?

Yes, our 2019 property listings offer a large selection of 148 vacation rentals near Winchester. From 72 Houses to 24 Condos/Apartments, 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:

  • Spofford Lake: 124 vacation rentals
  • United States Navy Seabee Bridge: 554 vacation rentals
  • Mount Wachusett Community College: 35 vacation rentals
  • Monadnock State Park: 84 vacation rentals
  • Brattleboro Common: 550 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 72 Houses in Winchester. Our other popular types of vacation rentals in Winchester include:

  • Condos/Apartments: 24 rentals available
  • Cabins: 31 rentals available
  • Cottages: 31 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 10 vacation rentals with pool available in Winchester. Please use our search bar to access the selection of vacation rentals available.