Winchester vacation rentals
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Find the best place to stay - Winchester
Quaint cottage located directly on Long Meadow Pond
Top rated rentals - Winchester
Photo gallery for River Overlook - Check the view from your deck!
Great 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
Find the perfect vacation rental for your Winchester getaway
Learn about the unique charm of Winchester with a stay in a private vacation home. There's no shortage of things to see and do in the area.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.
Sightseeing in and around Winchester
Are you hoping to find attractions to see in the city? Venture out of your vacation home and check out everything that makes Winchester a fun spot to vacation. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:
- Connecticut Valley Winery (8.3 mi / 13.4 km)
- Ski Sundown (9.4 mi / 15.2 km)
- Mohawk Mountain Ski Area (12.4 mi / 20 km)
- Harney and Sons Tea Tasting Room (16.2 mi / 26 km)
- Talcott Mountain State Park (17.9 mi / 28.8 km)
- Sunset Meadow Vineyards (11.1 mi / 17.9 km)
Exploring the natural landscape of Winchester
Whether you're an active traveler or just want to appreciate the scenery, Winchester is a great spot to appreciate mother nature. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:
- Highland Lake (2.6 mi / 4.3 km)
- Satan's Kingdom State Recreation Area (9.5 mi / 15.4 km)
- Woodridge Lake (11.5 mi / 18.6 km)
- Mohawk Mountain State Forest (12.2 mi / 19.6 km)
- Litchfield Town Green (13.6 mi / 22 km)
- Otis Reservoir (15.3 mi / 24.6 km)
How to get to and around Winchester
Fly into Bradley Intl. Airport (BDL), the closest airport, located 21.9 mi (35.2 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to Westfield, MA (BAF-Barnes Municipal), which is 25.8 mi (41.5 km) away.