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Check prices for these dates

Next weekend
May 22 - May 24
In two weeks
May 29 - May 31

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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, (417 reviews)
"Clean, good breakfast, friendly staff"
United States
Debra
The price is ￥16,668
￥19,168 total
includes taxes & fees
May 17 - May 18
Locust Tree Bed and Breakfast LLC
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,004 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
The price is ￥13,421
￥14,991 total
includes taxes & fees
May 19 - May 20
Quality Inn Great Barrington
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (48 reviews)
"Very comfortable bed, that was mostly what I cared about. I got my beauty sleep)"
United States
Maria
The price is ￥26,263
￥29,336 total
includes taxes & fees
May 20 - May 21
Wilder House Berkshires
Property entrance

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (106 reviews)
"Room was spotless and hospitality was outstanding. Had great breakfast and was very welcoming. "
United States
Desiree
The price is ￥22,224
￥24,669 total
includes taxes & fees
May 18 - May 19
Truman Gillet House Bed & Breakfast
Exterior

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 ￥22,065
￥25,375 total
includes taxes & fees
May 25 - May 26
Home2 Suites by Hilton Bristol
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, (854 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is ￥10,833
￥12,100 total
includes taxes & fees
May 25 - May 26
Monument Mountain Motel
Restaurant

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 ￥29,645
￥34,091 total
includes taxes & fees
Jun 16 - Jun 17
The Abner Hotel
Room, 2 Queen Beds, Refrigerator | Premium bedding, desk, laptop workspace, blackout drapes

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very Good, (856 reviews)
"very friendly, room was nice and breakfast was great"
United States
Lawrence
The price is ￥19,390
￥21,659 total
includes taxes & fees
May 28 - May 29
Hampton Inn Westfield
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (178 reviews)
"Great staff. "
United States
wesley
The price is ￥22,244
￥25,581 total
includes taxes & fees
May 25 - May 26
Blackberry River Inn
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (559 reviews)
"A nice safe and quiet place to stay. Park right in front of your door. My dog loved the large grass area. The room was large and the beds very comfortable. The heat was on when we arrived which was great . It was cold and snowy that day. I loved having the self check-in and check out. We plan on going back the next time we are in the area. "
United States
SUSAN
The price is ￥15,080
￥16,845 total
includes taxes & fees
Jun 11 - Jun 12
The Little Lion
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)
"Rooms were fresh and clean, staff is very friendly and accommodating!"
United States
Amanda
The price is ￥14,301
￥16,446 total
includes taxes & fees
May 25 - May 26
Days Inn by Wyndham Torrington
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, (1,150 reviews)
" Clean room, nice staff, good breakfast."
United States
Yvan
The price is ￥19,322
￥22,221 total
includes taxes & fees
Jun 14 - Jun 15
Holiday Inn Express & Suites Bradley Airport by IHG
Free daily buffet breakfast

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (927 reviews)
"Very clean& maintained. Most comfortable bed I've slept in"
United States
Keith
The price is ￥16,057
￥17,936 total
includes taxes & fees
Jun 10 - Jun 11
Quality Inn Westfield - Springfield
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
9.4 out of 10, Exceptional, (44 reviews)
"The East Rock Inn is great. It's comfortable, clean and close to downtown Great Barrington. This was my second time staying here."
United States
Laura
The price is ￥20,980
￥23,435 total
includes taxes & fees
May 17 - May 18
East Rock Inn
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, (578 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
The price is ￥11,879
￥13,270 total
includes taxes & fees
May 25 - May 26
Travelodge by Wyndham Great Barrington Berkshires
Exterior

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.8 out of 10, Exceptional, (6 reviews)
"The new owners have done a great job. The place is immaculate, the room was very comfortable and well appointed, the common areas charming. Highly recommended."
United States
Robert
The price is ￥30,121
￥33,647 total
includes taxes & fees
May 20 - May 21
The Berkshire Mountain Inn
Front of property

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (137 reviews)
"Beautiful property and rooms."
United States
Kara
The price is ￥23,801
￥26,110 total
includes taxes & fees
May 17 - May 18
Gedney Farm
Exterior

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington
2.5 star property
Farmington
9.0 out of 10, Wonderful, (1,000 reviews)
"Clean room, friendly staff and quiet grounds."
United States
shaneice
The price is ￥21,478
￥24,700 total
includes taxes & fees
Jun 1 - Jun 2
Hampton Inn & Suites Hartford/Farmington
Exterior

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.4 out of 10, Very Good, (26 reviews)
"Nice staff, great restaurant at the inn. Very cute town. "
United States
Valerie
The price is ￥36,587
￥41,389 total
includes taxes & fees
Jun 4 - Jun 5
The Millerton Inn
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, (780 reviews)
"Staff was lovely, everything was easy, clean and comfortable"
United States
Helena
The price is ￥30,899
￥34,513 total
includes taxes & fees
Jun 1 - Jun 2
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.
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
Old houses in the Old Salem Historic District, in downtown Winst

Top Winsted Hotel Reviews

Avon Old Farms Hotel

Avon Old Farms Hotel

10/10 Excellent
"A great location, with great amenities. Staff at desk, housekeeping and breakfast was excellent. Comfortable bed and linens, with real towel. Perfect for a multiday business stay and saw a number of families getting together for weddings."
Andy 2-night trip
Posted 11 hours ago
Avon Old Farms Hotel

More cheap stays in Winsted

Quality Inn Great Barrington

Quality Inn Great Barrington

372 Main Street Great Barrington MA
The price is ￥13,421 per night from May 19 to May 20
￥13,421
￥14,991 total
May 19 - May 20
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)

Frequently asked questions

Where is the best place to stay in Winsted?
The Farmington Inn & Suites, located 18 mi (29 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 Sheraton Hartford Hotel at Bradley Airport and Hampton Inn & Suites Hartford/Farmington. 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 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?
Hampton Inn & Suites Hartford/Farmington: Features daily, an indoor pool, and complimentary wired internet access. Avon Old Farms Hotel and Homewood Suites by Hilton Hartford-Farmington 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 20 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 The Marina at Highland Lake. A couple of additional sights to add to your agenda are Northwestern Connecticut Community College Library and American Mural Project. 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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