Photo by Kim Knox Beckius

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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)
"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 SAR 596
SAR 750 total
includes taxes & fees
1 Jan - 2 January 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)
"We stay here every year and it never disappoints "
United States
Elizabeth
The price is SAR 383
SAR 427 total
includes taxes & fees
28 Jan - 29 January 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)
"Very pet friendly and the night check in agent was super kind and friendly"
United States
olivia townsend
The price is SAR 434
SAR 484 total
includes taxes & fees
21 Jan - 22 January 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)
"My go to place for my ski weekends"
United States
Ryan
The price is SAR 284
SAR 317 total
includes taxes & fees
13 Jan - 14 January 2026
Quality Inn Great Barrington

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 SAR 413
SAR 461 total
includes taxes & fees
1 Jan - 2 January 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)
"Amazing stay"
United States
Marquise
The price is SAR 535
SAR 615 total
includes taxes & fees
11 Jan - 12 January 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)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is SAR 394
SAR 453 total
includes taxes & fees
31 Dec - 1 January 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)
"Pleasant hosts, quiet area, big soaking sub, we enjoyed our stay."
United States
michelle
The price is SAR 525
SAR 583 total
includes taxes & fees
31 Dec - 1 January 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)
"The room was very clean, and the check-in staff was very courteous."
United States
Kristin
The price is SAR 394
SAR 453 total
includes taxes & fees
9 Jan - 10 January 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, (1003)
"Close to airport. "
United States
Angela
The price is SAR 427
SAR 492 total
includes taxes & fees
25 Jan - 26 January 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)
"Always my go to hotel when I come home for visits, friendly staff, clean hotel. "
United States
Kathleen
The price is SAR 443
SAR 509 total
includes taxes & fees
5 Jan - 6 January 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 SAR 281
SAR 314 total
includes taxes & fees
31 Dec - 1 January 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)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is SAR 616
SAR 709 total
includes taxes & fees
5 Jan - 6 January 2026
Blackberry River Inn

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 SAR 1,166
SAR 1,397 total
includes taxes & fees
25 Jan - 26 January 2026
Delamar West Hartford

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 SAR 352
SAR 393 total
includes taxes & fees
21 Jan - 22 January 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)
"Clean room, staff, amenities "
United States
Jae
The price is SAR 434
SAR 499 total
includes taxes & fees
30 Jan - 31 January 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)
"A delightful stay from beginning to end - clean, bright, beautiful in a lovely are of the state. "
United States
Lori
The price is SAR 1,090
SAR 1,253 total
includes taxes & fees
1 Jan - 2 January 2026
The Litchfield Inn

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 SAR 401
SAR 461 total
includes taxes & fees
3 Jan - 4 January 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)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is SAR 506
SAR 566 total
includes taxes & fees
14 Jan - 15 January 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

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

Hotels in Winsted with star-rating

Find out more about Winsted

Top reasons to visit Winsted

  • Outdoor Adventures: Winsted offers a range of outdoor activities, including skiing, hiking, and exploring nearby national parks and nature reserves.
  • Scenic Beauty: The picturesque landscapes and recreational areas provide stunning views and perfect spots for relaxation.
  • Charming Downtown: Enjoy delightful shopping and dining experiences in the quaint downtown area.
  • Victorian Mansions: Discover the historical charm of beautifully preserved Victorian mansions throughout the town.
  • Accommodations for Everyone: Winsted has diverse lodging options catering to families, business travelers, and pets.

Find great hotels near Winsted

Explore the charming accommodations in Winsted, Connecticut, where a variety of lodging options await you. Whether you're traveling with family, on business, or with pets, you'll find hotels that cater to your needs. From cozy, family-friendly spots to pet-friendly facilities, Winsted offers a welcoming atmosphere for every traveler. Discover the best hotels and read reviews to ensure a memorable stay in this picturesque New England town.

  • La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport: A welcoming hotel designed for families and pet lovers, La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport offers a warm atmosphere perfect for travelers seeking comfort and convenience. Located 32.2km from Winsted, this pet-friendly property features amenities tailored for children, including free cribs and window guards for safety. Guests appreciate the LGBTQIA-friendly environment and the ability to bring their furry companions along, making it ideal for those traveling with pets. With a commitment to inclusivity and family-friendly services, this hotel is a great choice for a relaxed getaway.
  • Homewood Suites by Hilton Hartford-Farmington: This 3-star hotel, situated 30.6km from Winsted, caters to both business travelers and families, providing a blend of comfort and practicality. Homewood Suites by Hilton Hartford-Farmington is known for its spacious suites that come equipped with kitchen facilities, perfect for longer stays. The hotel is pet-friendly, allowing dogs and cats, and offers a welcoming environment for LGBTQIA guests. With a focus on business amenities and family-friendly policies, this hotel ensures a balanced experience for all types of travelers, making it an excellent choice for extended vacations or work-related trips.
  • The Farmington Inn & Suites: Just 29.0km from Winsted, The Farmington Inn & Suites is a charming 3-star hotel that combines business functionality with a pet-friendly atmosphere. This inn is ideal for those on work trips or leisure vacations, providing a comfortable setting for relaxation. Guests can enjoy the convenience of on-site amenities while feeling at home with their pets, as the hotel allows dogs and cats. The Farmington Inn & Suites also prides itself on its welcoming service and cozy ambiance, making it a delightful choice for visitors seeking a pleasant stay in the area.

Where to stay near Winsted

Winsted, Connecticut, is a charming destination perfect for outdoor enthusiasts and romantic getaways. Explore the scenic beauty of its parks and recreational areas, while the downtown area offers delightful shopping for enthusiasts. Don’t miss the stunning Victorian mansions that add a touch of history to your visit. Whether you're seeking relaxation or adventure, Winsted and its surrounding neighborhoods provide a family-friendly atmosphere ideal for creating unforgettable memories.

  • Simsbury: Nestled 22.5km from Winsted, Simsbury is a charming town known for its picturesque landscapes and outdoor activities. The area attracts visitors year-round, with peak travel months in April, July, and September. Travelers flock to Simsbury for its romantic ambiance and stunning scenery. Enjoy a variety of activities, from visiting local arts centers to attending music concerts. Key attractions include a beautiful lake, a historic college, and a unique event conference venue that host various community gatherings and celebrations.
  • Riverton: Located just 6.4km from Winsted, Riverton is a delightful small town that thrives on its natural beauty. With peak visitor numbers during the summer months of July and August, this area is perfect for those looking to experience outdoor adventures. Riverton is renowned for its scenic landscapes, making it an ideal location for romantic getaways or peaceful retreats. Popular activities include skiing and golfing, with local attractions featuring a serene lake, a national state park, and a picturesque river, perfect for exploring nature's wonders.
  • New Hartford: Approximately 8.0km from Winsted, New Hartford presents an inviting atmosphere for outdoor enthusiasts. The town sees an influx of visitors during the summer months, particularly from June to August. Known for its romantic settings and scenic beauty, New Hartford offers numerous opportunities for skiing and winter sports. Visitors can explore a local lake, enjoy the tranquility of a national state park, or relax in one of its lovely parks. Whether you're seeking adventure or relaxation, New Hartford has something for everyone.

Things to do in and around Winsted

Winsted, Connecticut, is an ideal destination for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can enjoy skiing at local ski fields, explore beautiful recreational areas, and participate in outdoor adventures. Major attractions include scenic landscapes and family-friendly amusement parks, making it a perfect spot for fun and relaxation. Experience the charm of Winsted while engaging in its various outdoor activities.

Shopping

Ames Plaza Shopping Center, located 1.6km away from Winsted, offers a variety of shops and a lively atmosphere perfect for families and friends. If you're up for a drive, Rosedale Farms & Vineyards is 22.5km away, and Bloomfield Crossing is 29.0km away, both featuring unique shopping experiences.

Recreation

Explore Satan's Kingdom State Recreation Area for serene hiking and reconnecting with nature, just 11.3km from Winsted. Attend a concert at Music Mountain, located 20.9km away, for entertainment and relaxation. For outdoor enthusiasts, Wintonbury Hills Golf Course, 25.7km away, offers a vibrant golfing experience.

Adventure

Ski Sundown offers thrilling skiing experiences just 11.3km from Winsted, perfect for snow sports enthusiasts. For motorsport fans, Lime Rock Park, located 111.3km away, provides exhilarating racing events. If you prefer hiking, the Big Cathedral Trail, 22.5km from Winsted, boasts stunning scenery and outdoor adventure.

Nightlife

Experience the lively atmosphere at Laurel Lanes, where you can enjoy arcade games and adventure vibes. For a touch of romance and culture, visit the nearby Warner Theater and Infinity Music Hall and Bistro, both offering captivating performances just a short drive away from Winsted.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Winsted

To save money on your trip to Winsted, Connecticut, consider visiting during the cheaper months of March or November to December, avoiding peak seasons like July and October. Booking your stay on a Monday can also lead to lower rates compared to Saturdays. Use Expedia's search tool to find affordable hotels by sorting prices from lowest to highest, and consider bundling your hotel, flights, and activities for additional savings. Look for deals on beverages and business amenities to maximize your budget while enjoying free local attractions.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Winsted are March and November to December, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Winsted is Monday. The most expensive day to stay in Winsted is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia's search tool to refine your choices based on your budget, desired location, and preferred hotel category. To find the best prices and offers, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Winsted hotel reservation with your flights and activities through an Expedia package.

Find the best attractions in and around Winsted

Winsted is perfect for those seeking outdoor and romantic getaways, offering stunning scenery and a variety of attractions. Visitors can explore nearby national parks, nature reserves, and local parks, ideal for eco-friendly adventures and outdoor activities. Whether you're looking for a peaceful retreat or an adventurous experience, Winsted has something to offer every nature enthusiast.

  • Burr Pond State Park: Located 6.4km from Winsted, this picturesque park offers stunning outdoor scenery and a range of adventurous activities. Enjoy hiking, fishing, and picnicking while surrounded by the tranquility of nature.
  • Winchester Historical Society: Situated within Winsted, this charming history museum immerses you in the local culture and heritage. Explore fascinating exhibits that highlight the area’s rich history and gain insight into its unique stories.
  • Enders State Forest: About 16.1km from Winsted, this expansive forest is perfect for outdoor enthusiasts. Experience breathtaking trails, serene landscapes, and the thrill of adventure as you hike or explore the diverse wildlife.

Best time to go to Winsted

The best time to visit Winsted can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Winsted falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Winsted falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.2°F (-3.8°C)Light RainMostly SunnySlightly LowAverage
February27.1°F (-2.7°C)Light RainMostly CloudyAverageAverage
March34.5°F (1.4°C)Light RainMostly CloudyAverageSlightly Low
April46.0°F (7.8°C)Light RainMostly CloudySlightly HighAverage
May57.4°F (14.1°C)Light RainMostly SunnyAverageAverage
June65.3°F (18.5°C)Light RainMostly SunnySlightly HighAverage
July71.6°F (22.0°C)Light RainMostly SunnySlightly HighSlightly High
August69.6°F (20.9°C)Light RainMostly SunnyAverageSlightly High
September62.8°F (17.1°C)Light RainMostly SunnyAverageAverage
October51.8°F (11.0°C)Light RainMostly SunnyAverageSlightly High
November39.9°F (4.4°C)Light RainMostly SunnySlightly LowSlightly Low
December31.3°F (-0.4°C)Light RainMostly CloudySlightly LowSlightly Low

The nearest major airports for your trip to Winsted

To visit Winsted, Connecticut, you have several airport options. Bradley International Airport (BDL) in Hartford, located 30.6km away, offers convenient access. Nearby hotels include the 4-star DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from BDL, and the Marriott Hartford Downtown, 19.3km away. Newburgh Stewart International Airport (SWF) is 96.6km from Winsted, with good hotel choices like The Dutchess Inn and Spa at Beacon, 9.7km from SWF. Lastly, Tweed New Haven Regional Airport (HVN) is 49.7km away, with nearby options such as the Omni New Haven Hotel at Yale, only 4.8km from HVN.

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 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 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: Provides daily, an indoor pool, and complimentary wired internet access. Hampton Inn & Suites Hartford/Farmington and Hampton Inn Hartford/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 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 Northwestern Connecticut Community College Library. A couple of additional sights to add to your agenda are Laurel Lanes 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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