Vacation rentals in Winchester
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Winchester vacation rentals
Other great vacation rentals in Winchester
Guest favourite
Home in Cornwall
4.99 out of 5 average rating, 91 reviewsThe Brookside Barn
Guest favourite
Home in New Hartford
4.94 out of 5 average rating, 49 reviewsPrivate Woodland Sanctuary—3 mins to a lake beach!
Guest favourite
Guesthouse in Sharon
4.99 out of 5 average rating, 94 reviewsCottage with a Waterfall View
Superhost
Rental unit in Winsted
4.88 out of 5 average rating, 41 reviewsPeaceful country getaway from the hectic city life
Superhost
Home in Torrington
4.87 out of 5 average rating, 79 reviewsCharming Home in Litchfield County on a MAIN ROAD!
Guest favourite
Home in Winchester
4.88 out of 5 average rating, 25 reviewsWinchester House with wifi/high speed internet.
Guest favourite
Home in Winsted
4.95 out of 5 average rating, 22 reviewsNewly renovated lakefront home!
Guest favourite
Guest suite in Bristol
4.94 out of 5 average rating, 31 reviewsPrivate Cozy Pet friendly: Great for work/leisure
Destinations to explore
- New City Vacation rentals
- Long Island Vacation rentals
- Newark Vacation rentals
- Hoboken Vacation rentals
- Washington Vacation rentals
- Philadelphia Vacation rentals
- New York Vacation rentals
- Jersey City Vacation rentals
- Montreal Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Cape Cod Vacation rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom