Photo by Kim Knox Beckius

Find hotels in Winsted, CT from ￥13,448

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Dec 29 - Dec 30
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Dec 30 - Dec 31
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Jan 2 - Jan 4
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Our top choices for Winsted hotels

Front of property
Simsbury 1820 House

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1002)
"Very nice room, pleasant and helpful staff"
United States
Concetta
The price is ￥24,895
￥31,330 total
includes taxes & fees
Dec 30 - Dec 31
Simsbury 1820 House
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (714)
"We stay here every year and it never disappoints "
United States
Elizabeth
The price is ￥15,970
￥17,839 total
includes taxes & fees
Jan 28 - Jan 29, 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Room, 2 Queen Beds, Refrigerator | Premium bedding, desk, laptop workspace, blackout drapes
Hampton Inn Westfield

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very Good, (819)
"Very pet friendly and the night check in agent was super kind and friendly"
United States
olivia townsend
The price is ￥18,103
￥20,221 total
includes taxes & fees
Jan 21 - Jan 22, 2026
Hampton Inn Westfield
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (810)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
Lobby
Quality Inn Great Barrington

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1001)
"My go to place for my ski weekends"
United States
Ryan
The price is ￥11,845
￥13,230 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Quality Inn Great Barrington
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
The Little Lion

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (548)
"Perfect for pets "
United States
Maria
The price is ￥17,223
￥19,238 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Little Lion
Lobby
DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut
4.0 star property
Bristol
9.0 out of 10, Wonderful, (1004)
"Amazing stay"
United States
Marquise
The price is ￥22,339
￥25,690 total
includes taxes & fees
Jan 11 - Jan 12, 2026
DoubleTree by Hilton Hotel Bristol, Connecticut
Terrace/patio
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is ￥16,440
￥18,906 total
includes taxes & fees
Dec 30 - Dec 31
Locust Tree Bed and Breakfast LLC
Property grounds
Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (102)
"Pleasant hosts, quiet area, big soaking sub, we enjoyed our stay."
United States
michelle
The price is ￥21,920
￥24,331 total
includes taxes & fees
Dec 30 - Dec 31
Truman Gillet House Bed & Breakfast
Lobby
Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
2.5 star property
Plainville
8.6 out of 10, Excellent, (915)
"Great place stayed several times."
United States
Marlene D
The price is ￥16,440
￥18,906 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Fairfield Inn & Suites by Marriott Plainville
Free daily buffet breakfast
Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport
2.5 star property
Windsor
9.0 out of 10, Wonderful, (1002)
"Close to airport. "
United States
Angela
The price is ￥19,130
￥21,999 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hampton Inn Hartford/Airport
Exterior
Holiday Inn Express & Suites Bradley Airport by IHG

Holiday Inn Express & Suites Bradley Airport by IHG

Holiday Inn Express & Suites Bradley Airport by IHG
2.5 star property
Windsor Locks
9.0 out of 10, Wonderful, (1159)
"Always my go to hotel when I come home for visits, friendly staff, clean hotel. "
United States
Kathleen
The price is ￥18,475
￥21,246 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Holiday Inn Express & Suites Bradley Airport by IHG
In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (564)
"Excellent location!!"
United States
Abdul Samad
The price is ￥11,743
￥13,118 total
includes taxes & fees
Dec 30 - Dec 31
Travelodge by Wyndham Great Barrington Berkshires
Library
Blackberry River Inn

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (165)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is ￥25,733
￥29,593 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Blackberry River Inn
Lunch and dinner served
Delamar West Hartford

Delamar West Hartford

Delamar West Hartford
4.0 star property
West Hartford
9.8 out of 10, Exceptional, (1002)
"Clean room, great staff and overall warm atmosphere."
United States
Gavrosh
The price is ￥45,718
￥54,924 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Delamar West Hartford
Lobby
Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (905)
"We left too early for breakfast. Parking was fine "
United States
Virginia
The price is ￥14,639
￥16,351 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Quality Inn Westfield - Springfield
In-room safe, desk, blackout drapes, iron/ironing board
DoubleTree by Hilton Hartford - Bradley Airport

DoubleTree by Hilton Hartford - Bradley Airport

DoubleTree by Hilton Hartford - Bradley Airport
4.0 star property
Windsor Locks
8.2 out of 10, Very Good, (1003)
"Clean room, staff, amenities "
United States
Jae
The price is ￥17,968
￥20,663 total
includes taxes & fees
Jan 4 - Jan 5, 2026
DoubleTree by Hilton Hartford - Bradley Airport
Lobby sitting area
The Litchfield Inn

The Litchfield Inn

The Litchfield Inn
4.0 star property
Litchfield
9.0 out of 10, Wonderful, (963)
"A delightful stay from beginning to end - clean, bright, beautiful in a lovely are of the state. "
United States
Lori
The price is ￥45,487
￥52,310 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Litchfield Inn
Free daily buffet breakfast
Springhill Suites Marriott Airport

Springhill Suites Marriott Airport

Springhill Suites Marriott Airport
3.0 star property
Windsor Locks
8.6 out of 10, Excellent, (1004)
"Nice hotel and great staff!"
United States
Brett
The price is ￥16,753
￥19,266 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Springhill Suites Marriott Airport
Lobby
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (759)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is ￥21,137
￥23,610 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 Winsted attractions

Highland Lake

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

Northwestern Connecticut Community College

Walk around the campus at Northwestern Connecticut Community College as part of your travels around Winchester.
See properties

Learn more about Winsted

Highland Lake offers refreshing swimming and boating during summer months, with a small beach perfect for families. Explore the American Museum of Tort Law founded by Ralph Nader, then grab coffee at one of Main Street's welcoming cafes.

See all hotels in Winsted
A tractor up a tree! And, there's a picnic table underneath.
Photo by Kim Knox Beckius
Open Photo by Kim Knox Beckius

Top Winsted Hotel Reviews

Simsbury 1820 House

Simsbury 1820 House

10/10 Excellent
"Always enjoy our stay!"
Gary 5-night trip
Posted 2 days ago
Simsbury 1820 House

More cheap stays in Winsted

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

1 Batterson Park Rd Farmington CT
The price is ￥11,694 per night from Jan 1 to Jan 2
￥11,694
￥13,448 total
Jan 1 - Jan 2, 2026
includes taxes & fees
7.8/10 Good! (1,001 reviews)

Frequently asked questions

Where is the best place to stay in Winsted?
Sheraton Hartford Hotel at Bradley Airport, located 19.3 mi (31 km) from the heart of Winsted, is a top choice for your stay based on our traveler data. Two other options for your visit to the area are The Farmington Inn & Suites and Holiday Inn Express & Suites Bradley Airport by IHG. See all available top hotels, or vacation rentals in Winsted.
What are some of the best vacation home rentals in Winsted?
Peace and quiet on the lake: This vacation home rental near Winsted is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind. See all vacation rentals in Winsted.
If I need to cancel my hotel reservation in Winsted, will I receive a refund?
Yes, the majority of room reservations are fully refundable as long as you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If your reservation is non-refundable, you might be able to cancel it and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winsted.
Where can I learn more about changing or cancelling my trip to Winsted?
To access more information about changing or cancelling your trip to Winsted, head over to our customer service page.
What's the best high-end place to stay in Winsted?
Rock Hall Luxe Lodging is a luxury B&B with spa services and in-room fireplaces, and it's a popular choice for Expedia travelers looking for an elegant place to stay. Find more luxury hotels in Winsted.
What are some accommodations with pools in Winsted?
Holiday Inn Express & Suites Bradley Airport by IHG: Features daily, an indoor pool, and complimentary wired internet access. Avon Old Farms Hotel and DoubleTree by Hilton Hartford - Bradley Airport are two additional hotels that offer an onsite pool. View all hotels with pools in Winsted.
What's the best hotel for staying near Bradley International Airport (BDL)?
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport is a popular hotel, featuring free breakfast and free WiFi. It's located a short 0.8 mi (1.3 km) from Bradley Intl. Airport. Other choices within close proximity to the airport include La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport and Sheraton Hartford Hotel at Bradley Airport.
How is it staying in Winsted?
Travelers to Winsted will find plenty to explore and enjoy. In Winsted, there are 19 hotels and other accommodations to choose from. Find out more about Winsted.
What should I see while I'm in Winsted?
Favorite places to visit include Highland Lake, Burr Pond State Park, and Laurel Lanes. A couple of additional sights to add to your agenda are The Marina at Highland Lake and Northwestern Connecticut Community College Library. Check out what more to see and do in Expedia's Winsted guide.
What's the weather like in Winsted?
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 Winsted are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.

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