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Our top choices for Winchester hotels

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (222 reviews)
"Great place for a quick family getaway!!"
United States
Rosemary
The price is ₩247,351
₩284,453 total
includes taxes & fees
Jun 3 - Jun 4
Home2 Suites by Hilton Bristol

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1,000 reviews)
"Rooms were fresh and clean, staff is very friendly and accommodating!"
United States
Amanda
The price is ₩152,219
₩175,052 total
includes taxes & fees
May 27 - May 28
Days Inn by Wyndham Torrington

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (65 reviews)
"This is a gem of a place. I have stayed at the abner many times and am delighted to say it is always a treat. The hotel is warm charming sparkling clean and perfectly located with shopping and dining just outside your doors. The rooms are comfortably appointed with all the extras of a posh stay . The breakfast is a must and don’t skip the frittata. Dinner is a cozy culinary experience with an ample menu to cover many tastes but dine exquisitely. If open do not miss out on the rooftop lounge...
United States
laura
The price is ₩283,391
₩325,896 total
includes taxes & fees
Jun 22 - Jun 23
The Abner Hotel

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 ₩211,197
₩234,429 total
includes taxes & fees
May 24 - May 25
Truman Gillet House Bed & Breakfast

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (417 reviews)
"Clean, good breakfast, friendly staff"
United States
Debra
The price is ₩158,398
₩182,158 total
includes taxes & fees
Jun 3 - Jun 4
Locust Tree Bed and Breakfast LLC

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (49 reviews)
"the breakfast is from heaven. the house is beautiful. love the stay."
United States
Catherine
The price is ₩290,818
₩324,843 total
includes taxes & fees
Jun 4 - Jun 5
Wilder House Berkshires

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (181 reviews)
"Breakfast was great"
United States
Archna
The price is ₩236,273
₩271,714 total
includes taxes & fees
May 25 - May 26
Blackberry River Inn

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.6 out of 10, Good, (192 reviews)
"Clean"
United States
Young Hwan
The price is ₩134,261
₩154,400 total
includes taxes & fees
May 25 - May 26
PLYMOUTH MOTOR LODGE

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
9.0 out of 10, Wonderful, (1,003 reviews)
"Clean room, great pool area, good breakfast options."
United States
Monica
The price is ₩235,939
₩271,327 total
includes taxes & fees
Jun 4 - Jun 5
Hampton Inn & Suites Hartford/Farmington

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1,001 reviews)
"Awesome r[m, nice breakfast, excellent staff!"
United States
Julie
The price is ₩209,688
₩267,163 total
includes taxes & fees
May 25 - May 26
Simsbury 1820 House

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington
2.5 star property
Farmington
8.0 out of 10, Very Good, (1,000 reviews)
"Good coffee at breakfast. "
United States
Janet
The price is ₩157,628
₩181,272 total
includes taxes & fees
May 31 - Jun 1
Extended Stay America Suites Hartford Farmington

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 ₩234,566
₩257,318 total
includes taxes & fees
May 25 - May 26
Gedney Farm

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,003 reviews)
"Older buildings but clean and well maintained. Breakfast was good, staff was friendly."
United States
Linda
The price is ₩223,405
₩283,088 total
includes taxes & fees
Jun 1 - Jun 2
The Farmington Inn & Suites

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.4 out of 10, Very Good, (26 reviews)
The price is ₩378,796
₩428,514 total
includes taxes & fees
Jun 3 - Jun 4
The Millerton Inn

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.8 out of 10, (86 reviews)
"A little dated but clean. A room for the night for when I race at lime rock"
United States
William
The price is ₩196,112
₩225,529 total
includes taxes & fees
Jun 1 - Jun 2
Hitching Post Country Motel

Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very Good, (1,002 reviews)
"Great place to stay"
United States
Linda
The price is ₩209,688
₩274,103 total
includes taxes & fees
Jun 1 - Jun 2
Avon Old Farms Hotel

Elm Motel

Elm Motel
2.0 star property
Westfield
7.2 out of 10, Good, (123 reviews)
"Jeannie at the front desk was helpful and very welcoming. Room was renovated since my last visit. "
United States
WAYNE
The price is ₩134,261
₩149,965 total
includes taxes & fees
May 24 - May 25
Elm Motel

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (161 reviews)
"We stay here frequently…always super clean and the inn keepers are very kind."
United States
Tracy
The price is ₩319,209
₩367,090 total
includes taxes & fees
Jun 1 - Jun 2
Cornwall Inn and Lodge

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
3.0 star property
Plainville
8.4 out of 10, Very Good, (976 reviews)
"Pool was cold and not a lot of great breakfast options other than that amazing stay "
United States
Ayanna
The price is ₩172,994
₩198,943 total
includes taxes & fees
May 28 - May 29
Fairfield Inn & Suites by Marriott Plainville

DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut
4.0 star property
Bristol
9.0 out of 10, Wonderful, (1,000 reviews)
"Great place"
United States
Karuna
The price is ₩243,785
₩280,353 total
includes taxes & fees
Jun 7 - Jun 8
DoubleTree by Hilton Hotel Bristol, Connecticut
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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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 Hampton Inn & Suites Hartford/Farmington. See all available top hotels, or 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?
Hampton Inn & Suites Hartford/Farmington: Features daily, an indoor pool, and complimentary wired internet access. Avon Old Farms Hotel 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 16 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 Platt Hill State Park. A couple of additional sights to add to your agenda are The Marina at Highland Lake 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.