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Next weekend
Jun 19 - Jun 21
In two weeks
Jun 26 - Jun 28

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Our top choices for Winchester hotels

Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (420 reviews)
"Below average B&B"
United States
Larry
The price is ￥16,801
￥19,321 total
includes taxes & fees
Jun 15 - Jun 16
Locust Tree Bed and Breakfast LLC
Property entrance

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (109 reviews)
"Very nice and comfortable place to stay. I’d definitely return. Breakfast was great."
United States
Lawrence
The price is ￥22,434
￥24,902 total
includes taxes & fees
Jun 16 - Jun 17
Truman Gillet House Bed & Breakfast
Desk, free cribs/infant beds, rollaway beds, free WiFi

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1,010 reviews)
"Good clean place to stay "
United States
keith
The price is ￥15,663
￥18,012 total
includes taxes & fees
Jun 28 - Jun 29
Days Inn by Wyndham Torrington
Terrace/patio

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (227 reviews)
"Overall good stay"
United States
Susan
The price is ￥24,038
￥27,643 total
includes taxes & fees
Jul 1 - Jul 2
Home2 Suites by Hilton Bristol
Free WiFi, bed sheets

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.8 out of 10, (87 reviews)
"A little dated but clean. A room for the night for when I race at lime rock"
United States
William
The price is ￥20,801
￥23,921 total
includes taxes & fees
Jun 18 - Jun 19
Hitching Post Country Motel
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (53 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is ￥29,764
￥33,247 total
includes taxes & fees
Jul 12 - Jul 13
Wilder House Berkshires
Combined shower/tub, rainfall showerhead, towels, soap

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.6 out of 10, Good, (194 reviews)
"Clean"
United States
Young Hwan
The price is ￥13,102
￥15,068 total
includes taxes & fees
Jun 15 - Jun 16
PLYMOUTH MOTOR LODGE
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (186 reviews)
"beautiful inn"
United States
Maura
The price is ￥23,827
￥27,401 total
includes taxes & fees
Jun 21 - Jun 22
Blackberry River Inn
Exterior

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
9.0 out of 10, Wonderful, (1,012 reviews)
"Lovely hotel with great breakfast."
United States
Thomas
The price is ￥21,966
￥25,261 total
includes taxes & fees
Jul 2 - Jul 3
Hampton Inn & Suites Hartford/Farmington
Restaurant

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (68 reviews)
"This is my litchfield go to spot. The location is spectacular the staff is so friendly and professional the rooms are comfortable and well appointed. Breakfast is not to be missed and the restaurant is comfortable savvy . The rooftop is amazing (when open). "
United States
laura
The price is ￥39,235
￥45,121 total
includes taxes & fees
Jul 13 - Jul 14
The Abner Hotel
Staircase

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,004 reviews)
"Staff was very friendly accommodating and helpful"
United States
alecia
The price is ￥21,990
￥28,053 total
includes taxes & fees
Jun 21 - Jun 22
The Farmington Inn & Suites
Premium bedding, down comforters, Select Comfort beds, in-room safe

Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT
2.5 star property
Torrington
5.6 out of 10, (794 reviews)
"Great hotel. Good service."
United States
Anisha
The price is ￥20,429
￥23,493 total
includes taxes & fees
Jun 15 - Jun 16
Americas Best Value Inn Torrington CT
Bar (on property)

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport
3.5 star property
Windsor Locks
9.2 out of 10, Wonderful, (1,009 reviews)
"Great location right outside the airport. Food reasonably priced and delicious."
United States
Stacy
The price is ￥43,105
￥49,571 total
includes taxes & fees
Jul 5 - Jul 6
Sheraton Hartford Hotel at Bradley Airport
Free daily continental breakfast

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (165 reviews)
"A charming stopover on our weekend travels. Small, quiet and lovely. Nice conversation with the host over breakfast too."
United States
Janice
The price is ￥34,828
￥40,052 total
includes taxes & fees
Jun 14 - Jun 15
Cornwall Inn and Lodge
Exterior

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.6 out of 10, Excellent, (29 reviews)
"We had a beautiful experience, staff was very accommodating."
United States
Bernadette
The price is ￥40,236
￥45,517 total
includes taxes & fees
Jun 14 - Jun 15
The Millerton Inn
Desk, iron/ironing board, free WiFi, bed sheets

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington
2.5 star property
Farmington
8.0 out of 10, Very Good, (1,001 reviews)
"Room was clean and location in good area"
United States
Keith
The price is ￥18,722
￥21,530 total
includes taxes & fees
Jun 21 - Jun 22
Extended Stay America Suites Hartford Farmington
Lobby lounge

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
3.0 star property
Plainville
8.4 out of 10, Very Good, (989 reviews)
"Great Service and food was decent."
United States
Sy A
The price is ￥18,267
￥21,007 total
includes taxes & fees
Jul 1 - Jul 2
Fairfield Inn & Suites by Marriott Plainville
Front of property

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (137 reviews)
"Had a great stay. Beautiful location."
United States
Joan
The price is ￥28,979
￥31,790 total
includes taxes & fees
Jun 25 - Jun 26
Gedney Farm
Terrace/patio

DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut
4.0 star property
Bristol
9.0 out of 10, Wonderful, (1,008 reviews)
"Great place"
United States
Karuna
The price is ￥27,545
￥31,677 total
includes taxes & fees
Jun 28 - Jun 29
DoubleTree by Hilton Hotel Bristol, Connecticut
Porch

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very Good, (301 reviews)
"Great staff and location!"
United States
Stacie
The price is ￥35,910
￥41,297 total
includes taxes & fees
Jun 15 - Jun 16
Interlaken Inn & Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Stay near popular Winchester attractions

Highland Lake

Commune with nature and explore the great outdoors at Highland Lake during your travels in Winchester.
See properties

Top Winchester Hotel Reviews

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"Great location if you’re flying out of Hartford"
eilene 1-night trip
Posted less than an hour ago
Sheraton Hartford Hotel at Bradley Airport

More cheap stays in Winchester

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE

325 Main St Terryville CT
The price is ￥13,102 per night from Jun 15 to Jun 16
￥13,102
￥15,068 total
Jun 15 - Jun 16
includes taxes & fees
7.6/10 Good! (194 reviews)

Frequently asked questions

What's the best place for a stay in Winchester?
The Farmington Inn & Suites, located 20.6 mi (33.1 km) from the heart of Winchester, is a top choice for your stay based on our traveler data. Other good choices for your visit to the area are Sheraton Hartford Hotel at Bradley Airport and Avon Old Farms Hotel. See all available top hotels, or vacation rentals in Winchester.
What's the top vacation rental in Winchester?
Beautiful retreat in a lake community to the enjoy the summer season.: This vacation home rental outside of Winchester is located on a lake and offers a barbecue grill, laundry facilities, and a Smart TV to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. See all vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes! You'll find that most hotel reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you booked a non-refundable reservation, it might still be possible to cancel it and be given a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
Where can I learn more about changing or cancelling my trip to Winchester?
To access more information about picking new dates or cancelling your trip to Winchester, head over to our customer service page.
What are some hotels with pools in Winchester?
Avon Old Farms Hotel: Features a sauna, a seasonal outdoor pool, and buffet. Hampton Inn & Suites Hartford/Farmington and DoubleTree by Hilton Hotel Bristol, Connecticut are two additional hotels with an onsite pool. View all hotels with pools in Winchester.
What is staying in Winchester like?
Visitors to Winchester are sure to find plenty to explore and enjoy. In Winchester, there are 17 hotels and other accommodations to choose from. Find out more about Winchester.
What should I do while I'm visiting Winchester?
Favorite places to visit include Highland Lake, Burr Pond State Park, and The Marina at Highland Lake. A couple of additional sights to add to your agenda are Laurel Lanes and Winchester Historical Society. Check out what more to see and do in Expedia's Winchester guide.
What's the seasonal weather like in Winchester?
The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.

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