Photo by Kim Knox Beckius

Winsted Hotels

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Winsted hotels

Simsbury 1820 House

Simsbury 1820 House
4.0 star property
Simsbury Center
9.2 out of 10, Wonderful, (1004)
Immerse yourself in the historic charm of this restored inn, offering a peaceful atmosphere with an indoor pool and fitness centre. Enjoy free breakfast, then explore nearby attractions or rent bikes to discover the area's vineyards and performing arts venues.

"Friendly, welcoming, and helpful staff. The room was beautiful and clean. The bar and restaurant were cozy; drinks and food delicious. "
United States
Christina
The price is €170
includes taxes & fees
6 Jan - 7 Jan 2026
Simsbury 1820 House

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)
Experience comfort in Great Barrington at this welcoming hotel with clean rooms and attentive service. Visit nearby Lake Mansfield Park or explore the Housatonic River after enjoying the indoor pool, fitness centre, and complimentary WiFi.

"We stay here every year and it never disappoints "
United States
Elizabeth
The price is €93
includes taxes & fees
25 Jan - 26 Jan 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (819)
Located in Westfield, this hotel offers a complimentary breakfast that guests rave about. Take a refreshing dip in the indoor pool, work out in the fitness centre, or visit nearby General Wareham Park. Free WiFi and parking add convenience.

"Very pet friendly and the night check in agent was super kind and friendly"
United States
olivia townsend
The price is €111
includes taxes & fees
21 Jan - 22 Jan 2026
Hampton Inn Westfield

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (811)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very good, (1000)
Set in a serene location near Housatonic River Walk, this hotel offers free breakfast, WiFi, and parking. Enjoy the fitness centre or explore nearby trails for hiking and skiing. Guests praise the helpful staff and quiet atmosphere in this convenient Great Barrington retreat.

"My go to place for my ski weekends"
United States
Ryan
The price is €72
includes taxes & fees
13 Jan - 14 Jan 2026
Quality Inn Great Barrington

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (548)
Surrounded by natural attractions like Monument Mountain, this welcoming motel offers complimentary WiFi and parking. Daily housekeeping ensures comfort while the attentive staff enhances every stay in this charming Berkshires location.

"Perfect for pets "
United States
Maria
The price is €104
includes taxes & fees
1 Jan - 2 Jan 2026
The Little Lion

DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut
4.0 star property
Bristol
9.0 out of 10, Wonderful, (1004)
Experience peaceful moments at this Bristol hotel with a welcoming indoor pool and American cuisine at The Willows restaurant. Located near Pine Lake Park and Casey Field, guests appreciate the helpful staff, clean rooms, and convenient free WiFi and parking.

"Amazing stay"
United States
Marquise
The price is €139
includes taxes & fees
11 Jan - 12 Jan 2026
DoubleTree by Hilton Hotel Bristol, Connecticut

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)
Set in serene East Canaan, this welcoming B&B offers complimentary full breakfast daily and free self parking. Nearby Land of Nod Vineyard and Beckley Furnace Industrial Park provide local exploration opportunities. Guests consistently praise the helpful staff.

"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is €103
includes taxes & fees
1 Jan - 2 Jan 2026
Locust Tree Bed and Breakfast LLC

Truman Gillet House Bed & Breakfast

Truman Gillet House Bed & Breakfast
3.0 star property
Granby
9.6 out of 10, Exceptional, (102)
Discover cosy comfort at this Granby B&B offering complimentary full breakfast, WiFi, and parking. Nearby hiking trails provide outdoor adventure while McLean Game Refuge and Old New-Gate Prison & Copper Mine offer fascinating day trips. Bradley International Airport is just 14 minutes away.

"Pleasant hosts, quiet area, big soaking sub, we enjoyed our stay."
United States
michelle
The price is €132
includes taxes & fees
1 Jan - 2 Jan 2026
Truman Gillet House Bed & Breakfast

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
2.5 star property
Plainville
8.6 out of 10, Excellent, (917)
Experience tranquility at this Plainville hotel with an indoor swimming pool and 24-hour gym. Enjoy free breakfast, WiFi, and parking while being close to Crescent Lake and Relic Brewing Company. The exceptionally helpful staff ensures a peaceful, comfortable stay.

"The room was very clean, and the check-in staff was very courteous."
United States
Kristin
The price is €99
includes taxes & fees
8 Jan - 9 Jan 2026
Fairfield Inn & Suites by Marriott Plainville

Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport
2.5 star property
Windsor
9.0 out of 10, Wonderful, (1004)
Jump in the indoor pool or workout at the 24-hour fitness centre at this Windsor hotel near Bradley International Airport. Guests praise the helpful staff, and appreciate free breakfast, WiFi, and parking. Connecticut Convention Centre is a short drive away.

"Close to airport. "
United States
Angela
The price is €111
includes taxes & fees
25 Jan - 26 Jan 2026
Hampton Inn Hartford/Airport

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, (1157)
This Windsor Locks hotel offers complimentary breakfast and WiFi, plus convenient access to Connecticut Fallen Firefighters Memorial. After a morning swim in the indoor pool, explore nearby New England Air Museum. Comfortable beds and helpful staff ensure a pleasant stay.

"Always my go to hotel when I come home for visits, friendly staff, clean hotel. "
United States
Kathleen
The price is €115
includes taxes & fees
6 Jan - 7 Jan 2026
Holiday Inn Express & Suites Bradley Airport by IHG

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (565)
"Excellent location!!"
United States
Abdul Samad
The price is €71
includes taxes & fees
2 Jan - 3 Jan 2026
Travelodge by Wyndham Great Barrington Berkshires

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (166)
Located in a quiet area of Norfolk with free daily cooked-to-order breakfast, this B&B provides peaceful comfort near Haystack Mountain State Park. Enjoy complimentary WiFi and parking while the attentive staff ensures a relaxing countryside retreat.

"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is €161
includes taxes & fees
5 Jan - 6 Jan 2026
Blackberry River Inn

Delamar West Hartford

Delamar West Hartford
4.0 star property
West Hartford
9.8 out of 10, Exceptional, (1001)
Stylish rooms await at this wellness-focused hotel with an upscale restaurant and bar. Relax with rejuvenating treatments at the full-service spa after exploring Blue Back Square. Free WiFi and parking complement the 24-hour fitness centre.

"Clean room, great staff and overall warm atmosphere."
United States
Gavrosh
The price is €317
includes taxes & fees
25 Jan - 26 Jan 2026
Delamar West Hartford

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (906)
Enjoy peaceful accommodation praised by travellers for their quiet atmosphere. This business-friendly hotel provides free breakfast, WiFi, and parking, with helpful staff ready to assist. Conveniently located near General Wareham Park and Gateway Entrance Park.

"We left too early for breakfast. Parking was fine "
United States
Virginia
The price is €89
includes taxes & fees
21 Jan - 22 Jan 2026
Quality Inn Westfield - Springfield

DoubleTree by Hilton Hartford - Bradley Airport

DoubleTree by Hilton Hartford - Bradley Airport
4.0 star property
Windsor Locks
8.0 out of 10, Very good, (1000)
Just 1.6 mi from Bradley Airport, this quiet retreat offers a bar, restaurant, and 24-hour fitness centre. Guests love the peaceful atmosphere, helpful staff, and convenient location near Northwest Park and Connecticut Fallen Firefighters Memorial.

"Clean room, staff, amenities "
United States
Jae
The price is €113
includes taxes & fees
30 Jan - 31 Jan 2026
DoubleTree by Hilton Hartford - Bradley Airport

The Litchfield Inn

The Litchfield Inn
4.0 star property
Litchfield
9.0 out of 10, Wonderful, (963)
Pamper yourself at this spa retreat with complimentary breakfast and free parking. Enjoy deep-tissue massages or visit the 24-hour fitness centre after exploring White Memorial Conservation Centre. Helpful staff ensure a comfortable stay near Mount Tom State Park.

"A delightful stay from beginning to end - clean, bright, beautiful in a lovely are of the state. "
United States
Lori
The price is €284
includes taxes & fees
1 Jan - 2 Jan 2026
The Litchfield Inn

Springhill Suites Marriott Airport

Springhill Suites Marriott Airport
3.0 star property
Windsor Locks
8.6 out of 10, Excellent, (1000)
Travellers praise the helpful staff at this hotel, just 1.3 mi from the airport. Jump into the indoor pool, hit the 24-hour fitness centre, or enjoy free breakfast. Connecticut Fallen Firefighters Memorial and New England Air Museum are nearby.

"Nice hotel and great staff!"
United States
Brett
The price is €105
includes taxes & fees
6 Jan - 7 Jan 2026
Springhill Suites Marriott Airport

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)
Tranquil accommodation in Great Barrington offer soundproof rooms for undisturbed sleep. The helpful staff, complimentary breakfast, and free parking enhance your stay, while restaurants within walking distance and nearby Housatonic River provide convenient exploration options.

"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is €128
includes taxes & fees
19 Jan - 20 Jan 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.
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Winsted attractions

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.

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

More cheap stays in Winsted

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 traveller data. Two other options for your visit to the area are Extended Stay America Suites Hartford Farmington 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 holiday rentals that Winsted has to offer?
Peace and quiet on the lake: This holiday home rental outside of Winsted is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most 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, you'll find most room reservations are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel 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.
What's the best luxury 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 travellers looking for an elegant place to stay. Find more luxury hotels in Winsted.
What are some accommodation options with pools in Winsted?
Holiday Inn Express & Suites Bradley Airport by IHG: Provides daily, an indoor pool and complimentary high-speed (wired) Internet access. Hampton Inn & Suites Hartford/Farmington and Hampton Inn Hartford/Airport are two additional hotels with an on-site pool. View all hotels with pools in Winsted.
What's it like staying in Winsted?
Travellers to Winsted will find plenty to explore and enjoy. In Winsted, there are 20 hotels and other accommodation options to choose from. Find out more about Winsted.
What should I see while I'm in Winsted?
Favourite places to visit include Highland Lake, Burr Pond State Park and Northwestern Connecticut Community College Library. A couple of additional sights to add to your itinerary are Laurel Lanes and American Mural Project. Take a look at what more there is to see and do in Expedia's Winsted guide.
What's the seasonal weather like in Winsted?
The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Winsted are January, February, March and April, with each month seeing an average of 15 cm of snowfall.

Explore a world of travel with Expedia