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Our top choices for Winsted hotels

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (834 reviews)
"Nice place and very reasonable for great location "
United States
Raymond
$67 nightly
The price is $74
Mar 26 - Mar 27
Total with taxes and fees
Monument Mountain Motel

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1,001 reviews)
"Great location, friendly staff"
United States
James
$67 nightly
The price is $75
Apr 8 - Apr 9
Total with taxes and fees
Quality Inn Great Barrington

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (203 reviews)
"Great place good people decent breakfast great room service "
United States
JULES
$130 nightly
The price is $150
Apr 2 - Apr 3
Total with taxes and fees
Home2 Suites by Hilton Bristol

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (416 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
$105 nightly
The price is $121
Mar 26 - Mar 27
Total with taxes and fees
Locust Tree Bed and Breakfast LLC

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
$150 nightly
The price is $168
Mar 26 - Mar 27
Total with taxes and fees
The Berkshire Mountain Inn

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
$140 nightly
The price is $155
Mar 29 - Mar 30
Total with taxes and fees
Truman Gillet House Bed & Breakfast

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
$148 nightly
The price is $166
Apr 20 - Apr 21
Total with taxes and fees
Wilder House 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, (574 reviews)
"Excellent location!!"
United States
Abdul Samad
$75 nightly
The price is $84
Mar 26 - Mar 27
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires

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, (752 reviews)
"Simple and clean hotel"
United States
Vitor
$107 nightly
The price is $120
Mar 30 - Mar 31
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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 attentive to my needs. I required support on two occasions during the length of my stay and they took care of the problem immediately. "
United States
Michele
$84 nightly
The price is $97
Mar 29 - Mar 30
Total with taxes and fees
Days Inn by Wyndham Torrington

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (555 reviews)
"Clean … check in , good location for us .. we’ll be back in Maynn"
United States
Kathleen
$110 nightly
The price is $123
Mar 26 - Mar 27
Total with taxes and fees
The Little Lion

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.4 out of 10, Exceptional, (40 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
$123 nightly
The price is $138
Apr 9 - Apr 10
Total with taxes and fees
East Rock Inn

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very Good, (836 reviews)
"Excelente "
Mexico
Angelica Enid Miranda
$110 nightly
The price is $123
Apr 12 - Apr 13
Total with taxes and fees
Hampton Inn Westfield

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.6 out of 10, Good, (184 reviews)
"Nice amount of space"
United States
Amanda
$74 nightly
The price is $86
Mar 26 - Mar 27
Total with taxes and fees
PLYMOUTH MOTOR LODGE

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.4 out of 10, Very Good, (18 reviews)
"Perfect "
United States
Zhigang
$172 nightly
The price is $195
Mar 29 - Mar 30
Total with taxes and fees
The Millerton Inn

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (919 reviews)
"Everything clean "
United States
GLADYS
$96 nightly
The price is $107
Apr 19 - Apr 20
Total with taxes and fees
Quality Inn Westfield - Springfield

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (172 reviews)
"Innkeeper was very accomodating and upgraded our room on his own. Lots of cozy common areas and a wonderful breakfast"
United States
arlene
$156 nightly
The price is $179
Apr 22 - Apr 23
Total with taxes and fees
Blackberry River Inn

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (55 reviews)
"My stay was flawless. From staff to the clean room and comfortable bedding all made for an amazing experience."
United States
Francis
$285 nightly
The price is $328
Mar 29 - Mar 30
Total with taxes and fees
The Abner Hotel

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, (1,145 reviews)
"Breakfast was great, staff was friendly and room was clean. "
United States
Jason
$110 nightly
The price is $127
Apr 1 - Apr 2
Total with taxes and fees
Holiday Inn Express & Suites Bradley Airport by IHG

Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville
3.0 star property
Plainville
8.6 out of 10, Excellent, (951 reviews)
"Average clean rooms, pool small, pizza Resterant good. Staff great at hotel and Resterant. "
United States
Kellie
$98 nightly
The price is $113
Mar 29 - Mar 30
Total with taxes and fees
Fairfield Inn & Suites by Marriott Plainville
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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.

Old houses in the Old Salem Historic District, in downtown Winst

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 is a paradise for outdoor enthusiasts, offering skiing, hiking trails, and breathtaking landscapes perfect for photography.
  • Charming Small Town: Explore the picturesque town and its rustic charm, ideal for relaxing getaways and leisurely strolls.
  • Family-Friendly Activities: Nearby Torrington provides a variety of attractions suitable for families, ensuring fun for all ages.
  • Unique Accommodations: Winsted offers diverse lodging options, including pet-friendly hotels and agritourism experiences.
  • Scenic Parks: Discover national and state parks that enhance eco-friendly experiences and adventure opportunities.

Find great hotels near Winsted

Explore a variety of hotel accommodations in Winsted, Connecticut, perfect for both leisure and business travelers. Whether you're seeking pet-friendly options or a unique agritourism experience, Winsted offers something for everyone. With convenient access to nearby attractions and an array of services tailored for adventure seekers, you'll find the ideal lodging to make your stay memorable. Discover hotels near Winsted and enjoy the charm of this picturesque town.

  • La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport: La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport is a budget-friendly hotel with a guest rating of 8.4. Located 20 miles from Winsted, this property is perfect for families, business travelers, and pet owners alike. The hotel offers a welcoming atmosphere with amenities tailored for children, including free cribs and window guards for safety. Pets are welcome, and the hotel has specific policies to ensure a comfortable stay for furry friends. Whether you’re traveling for business or leisure, La Quinta provides a cozy retreat.
  • Homewood Suites by Hilton Hartford-Farmington: Homewood Suites by Hilton Hartford-Farmington boasts a guest rating of 8.4 and is situated 19 miles from Winsted. This 3-star hotel is ideal for adventure seekers and business travelers. Guests can indulge in various recreational activities, including nearby skiing, snowboarding, and kayaking. The property is also pet-friendly, making it easy to bring your four-legged companions along on your trip. With spacious suites and a warm atmosphere, Homewood Suites ensures a fulfilling stay for both relaxation and adventure.
  • The Farmington Inn & Suites: The Farmington Inn & Suites is a charming 3-star hotel with a guest rating of 8.8, located 18 miles from Winsted. This property is particularly suited for business travelers and pet lovers. It offers a comfortable setting with amenities that cater to the needs of both professionals and their pets, including specific policies for pets and service animals. The hotel’s welcoming ambiance and convenient location make it an excellent choice for a memorable stay in the area.

Where to stay in and around Winsted

Winsted, Connecticut, is a charming destination perfect for outdoor enthusiasts and those seeking a romantic getaway. Explore the picturesque town and its surrounding areas, including the lovely city of Torrington, where family-friendly activities abound. Enjoy the scenic beauty and rustic charm that Winsted offers, making it a wonderful place to relax and recreate. Whether you seek adventure or tranquility, Winsted is sure to provide an unforgettable vacation experience.

  • Winchester: Nestled within Winsted, Winchester is a charming village that attracts visitors with its scenic beauty and outdoor activities. With traveler arrivals peaking in April, July, and September, this destination offers a moderately seasonal experience. Visitors can enjoy golfing, skiing, and stunning lake views. The local landmarks, including a marina and event conference venue, enhance the appeal, making Winchester a lovely spot for couples and families seeking a romantic or outdoor getaway.
  • West Hill Lake: Located 3 miles from Winsted, West Hill Lake is a picturesque village that welcomes travelers year-round, with peak visitation in July to August and October. This area is perfect for those seeking outdoor adventures, romantic strolls, and breathtaking scenery. Visitors can explore recreational areas, enjoy theater performances, and hit the golf course. The nearby beach and urban park provide ideal spots for relaxation and fun, making West Hill Lake a delightful escape.
  • Pleasant Valley: Situated 4 miles from Winsted, Pleasant Valley is a vibrant neighborhood that attracts visitors not only in summer but throughout the year. Peak months are July to August and October, as families and couples flock to enjoy its outdoor spaces and family-friendly attractions. With a charming boardwalk, theater, and educational opportunities, there's plenty to engage visitors. The local beach and esplanade are perfect for leisurely walks, making Pleasant Valley a wonderful destination for relaxation and family bonding.

Things to do in Winsted

Winsted, Connecticut, is perfect for outdoor enthusiasts and those seeking a romantic getaway. Visitors can enjoy skiing at local ski fields, explore scenic hiking trails, and discover beautiful landscapes ideal for photography. Don't miss local attractions and recreational areas for leisure activities. For fitness enthusiasts, there are gyms nearby to maintain your workout routine. Winsted offers a charming blend of nature and local exploration opportunities for an unforgettable vacation.

Shopping

In Winsted, you can find charming local shops for unique gifts and souvenirs. If you're up for a drive, check out the nearby Torrington Plaza, offering a variety of retail stores, or head to the larger Westfarms Mall for an extensive shopping experience.

Recreation

Winsted offers the tranquil experience of the Winsted Wellness Center, where you can enjoy yoga classes and holistic therapies. For outdoor recreation, the scenic Highland Lake features kayaking, fishing, and picturesque walking paths, perfect for relaxation and connecting with nature.

Adventure

Experience the thrill of hiking at the nearby Tungsten Ridge, offering breathtaking views and challenging trails. For water enthusiasts, the scenic Lake Winsted provides opportunities for kayaking and fishing, surrounded by picturesque landscapes that will make your adventure memorable.

Nightlife

Experience Winsted's nightlife at The Spare Time, where you can enjoy bowling and arcade games. For a cozy vibe, visit the Cornerstone Café for great coffee and live music. Don't miss the lively atmosphere at The Winsted Elks Lodge, featuring events and social gatherings throughout the week.

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

Booking tips and Expedia advantages for Winsted

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Winsted are March and December to January, 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: Expedia's search tool lets you customize your search by setting your budget, choosing your desired location, and more. You can easily arrange the results to display the lowest prices first, ensuring you find the most affordable hotels right away. Additionally, you can refine your search by hotel type; for instance, selecting the Eco-certified filter will show you sustainable and eco-friendly hotel options that you can book.
  • Consider bundling your trip: You can save money by combining your hotel stay in Winsted with your flights and activities by booking a package through Expedia.

Find the best attractions in and around Winsted

Winsted, Connecticut, is perfect for outdoor enthusiasts and those seeking romantic getaways. With its stunning scenery, visitors can explore a variety of attractions, including national and state parks, as well as nature reserves and local parks. These points of interest offer adventure and eco-friendly experiences, making Winsted an ideal destination for travelers looking to immerse themselves in nature.

  • Highland Lake: A serene escape right in Winsted, Highland Lake offers stunning scenery and a relaxing beach atmosphere. Perfect for romantic strolls or family picnics, you can enjoy water activities or simply unwind by the shore.
  • Winchester Historical Society: Immerse yourself in local culture at the Winchester Historical Society. This museum showcases the rich history of the area through engaging exhibits and artifacts, making it a great stop for history buffs and curious minds alike.
  • Burr Pond State Park: Located 4 miles from Winsted, Burr Pond State Park is an outdoor enthusiast's paradise. With its picturesque landscapes, hiking trails, and opportunities for adventure, it’s ideal for a day of exploration and relaxation in nature.

Best time to go to Winsted

The best time to visit Winsted is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.2°F (-3.8°C)Light RainMostly SunnySlightly LowSlightly Low
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 LowAverage
December31.3°F (-0.4°C)Light RainMostly CloudySlightly LowSlightly Low

The nearest major airports for your trip to Winsted

Traveling to Winsted, Connecticut, is convenient with access to major airports. New York's JFK Airport is located 96 miles away, with luxurious hotel options like Arlo Williamsburg and The William Vale, both 11 miles from the airport. Alternatively, LaGuardia Airport, 90 miles from Winsted, offers nearby accommodations such as The Plaza - A Fairmont Managed Hotel and The Pierre, A Taj Hotel, both just 5 miles away, providing various transportation services. Closer to Winsted, Hartford's Bradley International Airport is only 19 miles away, with hotel options like DoubleTree by Hilton Hartford - Bradley Airport, just 1 mile away, ensuring easy access for travelers.

Frequently asked questions

What is the best area to stay in Winsted?
The best area to stay in Winsted, Connecticut, is the downtown area, particularly around Main Street and Holabird Avenue.

This area forms the historic and commercial center of Winsted, offering convenient access to local businesses and the natural beauty of the surrounding Litchfield Hills. The downtown features a collection of shops, eateries, and public spaces, with the Still River flowing through parts of it. You'll find a mix of historic architecture and local establishments.

Couples looking for a quiet retreat will appreciate staying downtown. It provides a peaceful base to explore the local area, including nearby outdoor activities like hiking trails or visiting parks. The convenience of having local dining options within walking distance makes for a relaxed experience.

Solo travelers will also find the downtown area suitable. Its central location allows for easy exploration of Winsted's points of interest and provides simple access to main roads for day trips to other Litchfield County towns.
What are the best family hotels in Winsted?
For a highly-rated family-friendly hotel in Winsted, consider Rock Hall Luxe Lodging.

This 4.5-star hotel, with an exceptional 10.0 rating, offers several amenities that make it an excellent choice for families. Guests can enjoy complimentary full breakfast and free self-parking, adding convenience and value to their stay. The hotel also provides free rollaway extra beds, which is ideal for families. Free wired internet in public areas is also available.
What are the best spa hotels in Winsted?
For a luxurious spa experience in Winsted, Rock Hall Luxe Lodging is an excellent choice.

This 4.5-star hotel boasts a superb 10.0 review rating and features an onsite spa, allowing guests to relax and rejuvenate without leaving the property. Travelers also appreciate the complimentary full breakfast and free self-parking, adding to a convenient and indulgent stay. See all spa hotels in Winsted
What hotels in Winsted offer free breakfast?
For hotels in Winsted offering free breakfast, consider the Rock Hall Luxe Lodging.

The 4.5-star Rock Hall Luxe Lodging, with an outstanding 10.0 rating, provides a complimentary full breakfast daily, a highly valued amenity by guests. This hotel also offers free self-parking and free wired internet in public areas, adding to the convenience. Guests can enjoy the comfort of air-conditioned rooms, premium bedding, and designer toiletries. For recreation, there is an outdoor tennis facility on-site, and many rooms feature a cozy fireplace.
What are the most romantic hotels in Winsted for couples?
For a romantic getaway in Winsted, couples should consider Rock Hall Luxe Lodging.

This 4.5-star lodging, boasting a superb 10.0 review rating, offers a truly luxurious experience. Guests can enjoy the comfort of premium bedding, designer toiletries, and the cozy ambiance of a fireplace within their accommodations. The property also provides complimentary breakfast and free self-parking, adding to the convenience and value. For recreation, there is outdoor tennis available on-site, and for relaxation, guests can unwind in a hot tub or enjoy a private moment on a balcony.
When is the best time to go to Winsted?
The best time to go to Winsted is during the late spring, summer, and early fall months, specifically from May to October, to fully enjoy the area's natural beauty and outdoor activities.

During these months, the weather is generally pleasant, with warmer temperatures great for exploring Highland Lake, hiking the trails at Burr Pond State Park, or visiting local farms. Late spring offers blooming landscapes, while summer is ideal for water activities. Early autumn showcases the region's renowned fall foliage, providing stunning scenic drives and photo opportunities.

For those interested in outdoor recreation and scenic beauty, this extended period offers the most comfortable conditions and the widest array of activities.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Winsted.
How can I save on a Winsted hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Winsted hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Winsted hotel?
Prices for hotels in Winsted often vary, but you can find a great deal from $75 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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