Winchester vacation rentals
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Find the best place to stay - Winchester
Secluded chalet on 50 acres at base of Mt Monadnock, near lakes -TESLA charger
Top rated rentals - Winchester
Photo gallery for Cozy Cottage Along Idyllic Green River
Perfect little stay!
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
Take in the lakeside beauty of Winchester
The lake and forests provide a pleasant backdrop to your vacation home in Winchester. This city is relaxing and scenic, recognized for its canoeing, boating and kayaking. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.
Sightseeing in and around Winchester
Are you hoping to find attractions to see while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Winchester has to offer. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:
- Monadnock State Park (15.8 mi / 25.4 km)
- Cathedral of the Pines (20.1 mi / 32.3 km)
- Northfield Mountain Recreation Center (12 mi / 19.3 km)
- Brattleboro Country Club (12.2 mi / 19.6 km)
- Scott Farm Orchard (13 mi / 21 km)
- Brentwood Golf Course (14.9 mi / 23.9 km)
Exploring the natural features in Winchester
Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Winchester is a great place to get outside. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:
- Spofford Lake (10 mi / 16.1 km)
- Brattleboro Common (10.7 mi / 17.2 km)
- Turner Falls (14.2 mi / 22.8 km)
- Monadnock State Park (15.8 mi / 25.4 km)
- Greenfield Beach (16.6 mi / 26.8 km)
- Lake Dennison State Recreation Area (17.3 mi / 27.9 km)