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Check prices for these dates

Next weekend
Jun 5 - Jun 7
In two weeks
Jun 12 - Jun 14

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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
9.0 out of 10, Wonderful, (417 reviews)
"Great Place!!!"
United States
page
The price is NT$3,293
NT$3,787 total
includes taxes & fees
Jun 7 - Jun 8
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 NT$4,391
NT$4,874 total
includes taxes & fees
May 31 - Jun 1
Truman Gillet House Bed & Breakfast
Terrace/patio

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (224 reviews)
"Great place for a quick family getaway!!"
United States
Rosemary
The price is NT$5,614
NT$6,456 total
includes taxes & fees
Jun 1 - Jun 2
Home2 Suites by Hilton Bristol
Interior

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 NT$2,791
NT$3,210 total
includes taxes & fees
May 31 - Jun 1
PLYMOUTH MOTOR LODGE
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (183 reviews)
"beautiful inn"
United States
Maura
The price is NT$4,883
NT$5,616 total
includes taxes & fees
Jun 1 - Jun 2
Blackberry River Inn
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (50 reviews)
"My favorite place to stay! Always comfortable and breakfast was great."
United States
Allison
The price is NT$6,046
NT$6,753 total
includes taxes & fees
Jun 4 - Jun 5
Wilder House Berkshires
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 NT$4,077
NT$4,689 total
includes taxes & fees
May 31 - Jun 1
Hitching Post Country Motel
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, (1,002 reviews)
"Rooms were fresh and clean, staff is very friendly and accommodating!"
United States
Amanda
The price is NT$3,472
NT$3,992 total
includes taxes & fees
Jun 24 - Jun 25
Days Inn by Wyndham Torrington
Restaurant

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (65 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 NT$5,857
NT$6,735 total
includes taxes & fees
Jun 29 - Jun 30
The Abner Hotel
Staircase

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,001 reviews)
"Clean, friendly, accommodating"
United States
Dianne E.
The price is NT$4,009
NT$5,151 total
includes taxes & fees
Jun 7 - Jun 8
The Farmington Inn & Suites
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, (1,000 reviews)
"Good coffee at breakfast. "
United States
Janet
The price is NT$3,612
NT$4,154 total
includes taxes & fees
Jun 7 - Jun 8
Extended Stay America Suites Hartford Farmington
Reception

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1,000 reviews)
"Awesome r[m, nice breakfast, excellent staff!"
United States
Julie
The price is NT$4,359
NT$5,554 total
includes taxes & fees
Jun 1 - Jun 2
Simsbury 1820 House
Free daily continental breakfast

Cornwall Inn and Lodge

Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (164 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 NT$6,636
NT$7,632 total
includes taxes & fees
Jun 3 - Jun 4
Cornwall Inn and Lodge
Banquet hall

Avon Old Farms Hotel

Avon Old Farms Hotel
3.5 star property
Avon
8.4 out of 10, Very Good, (1,002 reviews)
"Just all around wonderful stay. Very quiet and comfortable."
United States
Grady
The price is NT$4,359
NT$5,698 total
includes taxes & fees
May 31 - Jun 1
Avon Old Farms Hotel
Exterior

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
9.0 out of 10, Wonderful, (1,002 reviews)
"Clean room, great pool area, good breakfast options."
United States
Monica
The price is NT$5,305
NT$6,101 total
includes taxes & fees
Jun 14 - Jun 15
Hampton Inn & Suites Hartford/Farmington
Exterior

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.4 out of 10, Very Good, (28 reviews)
"We had a beautiful experience, staff was very accommodating."
United States
Bernadette
The price is NT$7,875
NT$8,909 total
includes taxes & fees
May 31 - Jun 1
The Millerton Inn
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, (1,002 reviews)
"Great place"
United States
Karuna
The price is NT$5,305
NT$6,101 total
includes taxes & fees
Jun 21 - Jun 22
DoubleTree by Hilton Hotel Bristol, Connecticut
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 NT$5,817
NT$6,382 total
includes taxes & fees
Jun 18 - Jun 19
Gedney Farm
Lobby

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
3.0 star property
Plainville
8.4 out of 10, Very Good, (982 reviews)
"its was nice and cozy, the Amenities was also good. breakfast was on point and delicious, yummy .Rooms was a lil small but convenient. plenty of parking and being that it was next to the hwy, made it in my opinion, ideal. i would definitely stay there again."
United States
edgardo
The price is NT$3,826
NT$4,400 total
includes taxes & fees
Jun 10 - Jun 11
Fairfield Inn & Suites by Marriott Plainville
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, (1,001 reviews)
"Very convenient to airport when you have an early flight to catch. Parking safe and easy as well."
United States
Danielle
The price is NT$8,781
NT$10,099 total
includes taxes & fees
Jun 13 - Jun 14
Sheraton Hartford Hotel at Bradley Airport
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

The Litchfield Inn

The Litchfield Inn

8/10 Good
"Cozy and spacious"
Elsa 1-night trip
Posted 4 hours ago
The Litchfield Inn

More cheap stays in Winchester

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

492 East Main St Torrington CT
The price is NT$3,472 per night from Jun 24 to Jun 25
NT$3,472
NT$3,992 total
Jun 24 - Jun 25
includes taxes & fees
7.4/10 Good! (1,002 reviews)

Hotels in Winchester with star-rating

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.

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