Winchester holiday lettings
Find the best place to stay - Winchester
Quaint cottage located directly on Long Meadow Pond
Find spaces that suit your style
Top rated rentals - Winchester
Photo gallery for Cozy house with waterfall view!
Canton house
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Find the perfect holiday rental for your Winchester getaway
Learn about the unique charm of Winchester with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.
Sightseeing in and around Winchester
Do you want to discover top things to see and do in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Winchester a fun place to get away to. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:
- 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 looking for exciting outdoor activities or just want to appreciate the scenery, Winchester is a great place to spend some time outside. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:
- 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 Hartford, CT (BDL-Bradley Intl.), the closest airport, located 21.9 mi (35.2 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Westfield, MA (BAF-Barnes Municipal), which is 25.8 mi (41.5 km) away.