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Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness, and more.

Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
Rustic getaway in the beautiful Litchfield Hills of Northwestern Connecticut featuring a 2-acre pond and access to 9 miles of unique hiking trails on 450+ wooded acres. Cozy 1700's farmhouse comfortably sleeps 4 adults in 2 bedrooms, with an additional kids room that has a fold-out double futon and loft with one double air-mattress, perfect for children's sleeping bags. There is a pull out sofa in the living room. Dogs welcome! The house is next to Norbrook Farm Brewery, which you can walk to.
$264 per night
Vacation home in Torrington
Modern/Private Five ★ /Hotel quality stay/1 BR Apt
Enjoy the comfort and tranquility of this modern apt. A lovely space to relax after a busy day. This clean and bright apt offers a tranquil residential vibe alongside quick, easy access to the Torrington downtown areas, restaurants, stores and bars. It features an open-concept layout, a neutral color scheme, wood surfaces, tasteful furnishings and decor. Designed comfortably for your stay offering WiFi, Netflix, laundry, queen bed, well equipped kitchen, and clean fresh white bed sheets.
$135 per night
Cottage in Litchfield
Litchfield - Hot Tub - Mohawk Mountain - Fireplace
This vintage style cottage offers guests a comfortable and convenient stay in Litchfield with it’s range of amenities. Essential amenities include air conditioning, cooking basics, a dedicated workspace, dishes and silverware, a dryer, hair dryer, heating, hot tub, kitchen, TV, washer, and Wi-Fi. 5 Min - Litchfield Town center 9 Min - Arethusa Dairy farm- Restaurant 10 Min - White Memorial Conservation Center 8 Min - Bantam Lake 19 Min - Mohawk Mountain Ski Area
$72 per night

Stay near Winchester's top sights

Stop & Shop8 locals recommend
Kent Pizza4 locals recommend
Mario's Tuscany Grill11 locals recommend
R&B Sports World3 locals recommend
Little Red Barn Brewers5 locals recommend
Gilson Cinema & Cafe14 locals recommend

Other great vacation rentals in Winchester

Apartment in Simsbury
Ensign House Room
$124 per night
Apartment in Torrington
Apartment on Main St.
$99 per night
Cottage in Collinsville
The Carriage House
$146 per night
Guest suite in Canaan
Walk to Brewery in Historic Railroad Depot
$125 per night
Farm stay in West Simsbury
Flamig Farm Staycation
$145 per night
Apartment in Sheffield
Hideaway with Spectacular Berkshire Views
$135 per night
Guest suite in Morris
Lakeside Private Guest Suite
$90 per night
Apartment in Litchfield
Perfect, peaceful retreat
$114 per night
Guesthouse in Granby
The Loft @ Lost Acres ~ A Peaceful Rural Escape!
$129 per night
Apartment in Winsted
Haven at Highland lake
$86 per night
Guesthouse in New Hartford
Four Seasons New Hartford Airbnb
$101 per night
Apartment in Winsted
1st Floor The Inn at Highland Lake (Blue Door Inn)
$132 per night

Destinations to explore