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Check prices for these dates

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Feb 22 - Feb 23
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Feb 23 - Feb 24
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Feb 27 - Mar 1
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Mar 6 - Mar 8

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Our top choices for Winsted 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, (415 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is ₩151,858
₩174,637 total
includes taxes & fees
Feb 23 - Feb 24
Locust Tree Bed and Breakfast LLC
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (824 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
Monument Mountain Motel
Terrace/patio

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (192 reviews)
"Clean room, great staff"
United States
Tamiya
The price is ₩188,015
₩216,217 total
includes taxes & fees
Mar 1 - Mar 2
Home2 Suites by Hilton Bristol
Property entrance

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (104 reviews)
"Room was spotless and hospitality was outstanding. Had great breakfast and was very welcoming. "
United States
Desiree
The price is ₩202,478
₩224,751 total
includes taxes & fees
Feb 23 - Feb 24
Truman Gillet House Bed & Breakfast
In-room safe, desk, free cribs/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (571 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is ₩108,470
₩121,168 total
includes taxes & fees
Feb 23 - Feb 24
Travelodge by Wyndham Great Barrington Berkshires
Exterior

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, (1,174 reviews)
"Always my go to hotel when I come home for visits, friendly staff, clean hotel. "
United States
Kathleen
The price is ₩149,255
₩171,643 total
includes taxes & fees
Mar 2 - Mar 3
Holiday Inn Express & Suites Bradley Airport by IHG
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1,004 reviews)
"Clean room, great location"
United States
Andrea
The price is ₩95,772
₩106,977 total
includes taxes & fees
Mar 23 - Mar 24
Quality Inn Great Barrington
Exterior

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.2 out of 10, Very Good, (16 reviews)
"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 ₩233,124
₩263,721 total
includes taxes & fees
Feb 24 - Feb 25
The Millerton Inn
50-inch flat-screen TV with digital channels, Netflix, toys

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
The price is ₩289,254
₩323,097 total
includes taxes & fees
Feb 23 - Feb 24
The Berkshire Mountain Inn
Lobby

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very Good, (828 reviews)
"I will stay again"
United States
Jailene
The price is ₩157,730
₩176,185 total
includes taxes & fees
Mar 1 - Mar 2
Hampton Inn Westfield
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (43 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is ₩278,812
₩311,432 total
includes taxes & fees
Feb 25 - Feb 26
Wilder House Berkshires
Pet-friendly

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (553 reviews)
"Great friendly staff"
United States
Pablo
The price is ₩159,090
₩177,703 total
includes taxes & fees
Feb 23 - Feb 24
The Little Lion
Free daily buffet breakfast

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (917 reviews)
"Staff was very friendly. Everything was clean and well kept. Small hotel but very cozy and quiet."
United States
Gloria
The price is ₩133,635
₩149,271 total
includes taxes & fees
Mar 11 - Mar 12
Quality Inn Westfield - Springfield
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, (1,004 reviews)
"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 ₩117,133
₩134,705 total
includes taxes & fees
Feb 23 - Feb 24
Extended Stay America Suites Hartford Farmington
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, (1,001 reviews)
"Staff was very friendly, room was clean. Overall great stay, thanks!"
United States
Nathaniel
The price is ₩131,538
₩151,268 total
includes taxes & fees
Mar 16 - Mar 17
Days Inn by Wyndham Torrington
Exterior

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, (736 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is ₩149,255
₩166,717 total
includes taxes & fees
Mar 1 - Mar 2
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (38 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is ₩181,332
₩202,547 total
includes taxes & fees
Mar 20 - Mar 21
East Rock Inn
Staircase

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,004 reviews)
"This place is like a warm hug from your favorite auntie. "
United States
kieran
The price is ₩156,689
₩205,139 total
includes taxes & fees
Feb 25 - Feb 26
The Farmington Inn & Suites
Restaurant

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (51 reviews)
"My stay was flawless. From staff to the clean room and comfortable bedding all made for an amazing experience."
United States
Francis
The Abner Hotel
Exterior

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (767 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is ₩232,849
₩260,092 total
includes taxes & fees
Feb 26 - Feb 27
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

Highland Lake's crystal-clear waters span 445 acres across three bays, perfect for boating and fishing enthusiasts. Enjoy smallmouth bass fishing or kayak along Connecticut's scenic shoreline.
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Ledgebrook Plaza

This neighborhood shopping center offers convenient retail options anchored by Stop & Shop supermarket. Visit on weekday mornings for a relaxed experience and look forward to the addition of a Marshalls store in 2025.
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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
Old houses in the Old Salem Historic District, in downtown Winst

Top Winsted Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Great location, amenities, pool and hot tub for the kids, friendly staff, comfortable room."
Jennifer 2-night trip
Posted 3 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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 ₩117,133 per night from Feb 23 to Feb 24
₩117,133
₩134,705 total
Feb 23 - Feb 24
includes taxes & fees
7.8/10 Good! (999 reviews)

Frequently asked questions

Where is the best place to stay in Winsted?
Extended Stay America Suites Hartford Farmington, located 20 mi (32.2 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 Delamar West Hartford and Hampton Inn & Suites Hartford/Farmington. See all available top hotels, or 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?
Hampton Inn & Suites Hartford/Farmington: Features daily, an indoor pool, and complimentary wired internet access. Holiday Inn Express & Suites Bradley Airport by IHG and Springhill Suites Marriott 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 The Marina at Highland Lake, Highland Lake, and Burr Pond State Park. A couple of additional sights to add to your agenda are Ledgebrook Plaza and Platt Hill State Park. 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.