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Our top choices for Winchester hotels

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1,001 reviews)
  • cleanliness
    Modern Torrington motel offers easy access to local attractions and outdoor activities.
"Very respectable staff and clean environment "
United States
Hannah
The price is ₩121,497
₩139,722 total
includes taxes & fees
Feb 18 - Feb 19
Days Inn by Wyndham Torrington

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (415 reviews)
  • cleanliness
    Experience the charming Locust Tree B&B in East Canaan with free breakfast.
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is ₩151,601
₩174,341 total
includes taxes & fees
Feb 17 - Feb 18
Locust Tree Bed and Breakfast LLC

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.0 out of 10, Very Good, (13 reviews)
  • cleanliness
    Escape to a Mediterranean culinary gem in historic Millerton with complimentary perks.
"Antonia was wonderful and made our stay special. She was kind and warm and when we were initially unhappy with our room immediately rectified the situation and in the end our stay was perfect! It’s a charming hotel, clean and centrally located, walking distance to all the local shops in town."
United States
Jamie
The price is ₩232,729
₩263,276 total
includes taxes & fees
Feb 17 - Feb 18
The Millerton Inn

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (190 reviews)
  • cleanliness
    Comfortable suite-style rooms in Bristol with free breakfast and a relaxing hot tub.
"Clean room, great staff"
United States
Tamiya
The price is ₩187,697
₩215,852 total
includes taxes & fees
Feb 22 - Feb 23
Home2 Suites by Hilton Bristol

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (104 reviews)
  • cleanliness
    Historic Connecticut B&B surrounded by scenic trails and nature attractions.
"Room was spotless and hospitality was outstanding. Had great breakfast and was very welcoming. "
United States
Desiree
The price is ₩202,135
₩224,370 total
includes taxes & fees
Feb 17 - Feb 18
Truman Gillet House Bed & Breakfast

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Tranquil retreat with health club and complimentary breakfast in Farmington.
"This place is like a warm hug from your favorite auntie. "
United States
kieran
The price is ₩158,992
₩207,747 total
includes taxes & fees
Feb 22 - Feb 23
The Farmington Inn & Suites

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington
2.5 star property
Farmington
8.0 out of 10, Very Good, (1,002 reviews)
  • cleanliness
    Stay at a tranquil hotel with free breakfast and parking in Farmington.
"Great deal in the Hartford area. Large room, comfy bed and super nice people. Very convenient to I 95"
United States
Patricia
The price is ₩109,138
₩125,511 total
includes taxes & fees
Feb 17 - Feb 18
Extended Stay America Suites Hartford Farmington

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (168 reviews)
  • cleanliness
    Serene New England escape offers tranquil country setting with seasonal pool.
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is ₩237,292
₩272,886 total
includes taxes & fees
Feb 17 - Feb 18
Blackberry River Inn

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (43 reviews)
  • cleanliness
    Unwind in the Berkshires at this charming B&B with free weekend breakfast.
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is ₩278,339
₩310,904 total
includes taxes & fees
Feb 18 - Feb 19
Wilder House Berkshires

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
3.0 star property
Plainville
8.6 out of 10, Excellent, (933 reviews)
  • cleanliness
    Quiet haven near Crescent Lake with indoor pool and 24-hour fitness center.
"Rooms were clean and staff was courteous. "
United States
Keith
The price is ₩154,489
₩177,663 total
includes taxes & fees
Feb 20 - Feb 21
Fairfield Inn & Suites by Marriott Plainville

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
8.8 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    Experience New England comfort and amenities just 15 minutes from Hartford.
"Very comfortable room, very nice staff. Breakfast was great. "
United States
Michael
The price is ₩176,406
₩202,867 total
includes taxes & fees
Feb 28 - Mar 1
Hampton Inn & Suites Hartford/Farmington

Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very Good, (1,001 reviews)
"I love this hotel. Beds are so comfy, showers are hot with great water pressure, large bathrooms, nice amenities, friendly staff. "
United States
Ann
The price is ₩151,226
₩205,455 total
includes taxes & fees
Mar 11 - Mar 12
Avon Old Farms Hotel

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.6 out of 10, Good, (180 reviews)
  • cleanliness
    Relax in modern comfort just minutes from Terryville's top attractions.
"Good basic room, squeeky beds and the bathroom faucets doesnt turn off. Good value though for $103.50"
United States
David
The price is ₩115,506
₩132,832 total
includes taxes & fees
Feb 17 - Feb 18
PLYMOUTH MOTOR LODGE

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.6 out of 10, (81 reviews)
  • cleanliness
    Cozy Connecticut motel near hiking trails offers a gateway to outdoor adventures.
"Basic accommodation that was clean and easy."
United States
Elizabeth
The price is ₩187,697
₩215,851 total
includes taxes & fees
Feb 17 - Feb 18
Hitching Post Country Motel

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (157 reviews)
  • cleanliness
    Enjoy a refreshing country stay with a pool at this charming Cornwall Bridge inn.
"We stay here frequently…always super clean and the inn keepers are very kind."
United States
Tracy
The price is ₩305,512
₩351,339 total
includes taxes & fees
Feb 17 - Feb 18
Cornwall Inn and Lodge

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (51 reviews)
  • cleanliness
    Elevated modern hotel with a rooftop terrace near Litchfield Town Green.
"My stay was flawless. From staff to the clean room and comfortable bedding all made for an amazing experience."
United States
Francis
The price is ₩362,038
₩416,340 total
includes taxes & fees
Feb 18 - Feb 19
The Abner Hotel

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport
3.5 star property
Windsor Locks
9.2 out of 10, Wonderful, (1,004 reviews)
  • cleanliness
    Experience direct airport access with convenient 24-hour fitness at this Windsor Locks hotel.
"I love this Wonderful Location and the breakfast is astounding!"
United States
Mark
The price is ₩330,635
₩380,230 total
includes taxes & fees
Feb 28 - Mar 1
Sheraton Hartford Hotel at Bradley Airport

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very Good, (281 reviews)
  • cleanliness
    Lakeside resort with golf course access and seasonal outdoor pool offers a serene escape.
"Great"
United States
Jorge
The price is ₩258,588
₩297,376 total
includes taxes & fees
Feb 17 - Feb 18
Interlaken Inn & Resort

Elm Motel

Elm Motel
2.0 star property
Westfield
7.2 out of 10, Good, (123 reviews)
  • cleanliness
    Comfortable motel near Big E with convenient parking and 24/7 service.
"Very clean, lacking bathroom and bathroom storage. Good price."
United States
Daniel
The price is ₩142,938
₩159,657 total
includes taxes & fees
Feb 24 - Feb 25
Elm Motel

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Experience history and comfort at this restored 1820 inn with two lounges.
"Lovely staff, beautiful room, comfy bed, delicious fresh breakfast. "
United States
Debra
The price is ₩229,567
₩288,908 total
includes taxes & fees
Feb 17 - Feb 18
Simsbury 1820 House
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?
Sheraton Hartford Hotel at Bradley Airport, located 21.9 mi (35.2 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 The Farmington Inn & Suites and Extended Stay America 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. Simsbury 1820 House and Avon Old Farms Hotel 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 The Marina at Highland Lake, Highland Lake, and Burr Pond State Park. A couple of additional sights to add to your agenda are Winchester Historical Society and Platt Hill State Park. 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.