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Our top choices for Winsted hotels

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
$105 nightly
The price is $121
Feb 12 - Feb 13
Total with taxes and fees
Locust Tree Bed and Breakfast LLC

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (188 reviews)
"Clean room, great staff"
United States
Tamiya
$130 nightly
The price is $150
Feb 19 - Feb 20
Total with taxes and fees
Home2 Suites by Hilton Bristol

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
Feb 12 - Feb 13
Total with taxes and fees
Truman Gillet House Bed & Breakfast

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1,001 reviews)
"This was a perfect place to stay. Reasonably priced, very clean, and the young lady who worked the front desk in the evening was super friendly. We will definitely book here again. "
United States
Jerome
$76 nightly
The price is $85
Feb 25 - Feb 26
Total with taxes and fees
Quality Inn Great Barrington

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (821 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
$67 nightly
The price is $74
Feb 12 - Feb 13
Total with taxes and fees
Monument Mountain Motel

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
$200 nightly
The price is $223
Feb 12 - Feb 13
Total with taxes and fees
The Berkshire Mountain Inn

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
$186 nightly
The price is $208
Feb 18 - Feb 19
Total with taxes and fees
Wilder House Berkshires

Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington
2.0 star property
Torrington
7.4 out of 10, Good, (1,005 reviews)
"Very respectable staff and clean environment "
United States
Hannah
$84 nightly
The price is $97
Feb 15 - Feb 16
Total with taxes and fees
Days Inn by Wyndham Torrington

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (37 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
$133 nightly
The price is $149
Mar 6 - Mar 7
Total with taxes and fees
East Rock Inn

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.2 out of 10, Wonderful, (50 reviews)
"My stay was flawless. From staff to the clean room and comfortable bedding all made for an amazing experience."
United States
Francis
$217 nightly
The price is $250
Mar 4 - Mar 5
Total with taxes and fees
The Abner Hotel

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.0 out of 10, Very Good, (13 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
$161 nightly
The price is $182
Feb 15 - Feb 16
Total with taxes and fees
The Millerton Inn

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, (731 reviews)
"Great property, very accommodating. "
United States
Shanice
$107 nightly
The price is $120
Feb 22 - Feb 23
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington 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, (567 reviews)
"Excellent location!!"
United States
Abdul Samad
$75 nightly
The price is $84
Feb 12 - Feb 13
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires

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
$110 nightly
The price is $123
Feb 12 - Feb 13
Total with taxes and fees
The Little Lion

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (168 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
$159 nightly
The price is $183
Feb 12 - Feb 13
Total with taxes and fees
Blackberry River Inn

Elm Motel

Elm Motel
2.0 star property
Westfield
7.2 out of 10, Good, (123 reviews)
"Very clean, lacking bathroom and bathroom storage. Good price."
United States
Daniel
$89 nightly
The price is $99
Feb 12 - Feb 13
Total with taxes and fees
Elm Motel

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,001 reviews)
"This place is like a warm hug from your favorite auntie. "
United States
kieran
$123 nightly
The price is $142
Feb 25 - Feb 26
Total with taxes and fees
The Farmington Inn & Suites

PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.6 out of 10, Good, (180 reviews)
"Good basic room, squeeky beds and the bathroom faucets doesnt turn off. Good value though for $103.50"
United States
David
$77 nightly
The price is $89
Feb 18 - Feb 19
Total with taxes and fees
PLYMOUTH MOTOR LODGE

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (915 reviews)
"Staff was very friendly. Everything was clean and well kept. Small hotel but very cozy and quiet."
United States
Gloria
$94 nightly
The price is $104
Mar 1 - Mar 2
Total with taxes and fees
Quality Inn Westfield - Springfield

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very Good, (825 reviews)
"I will stay again"
United States
Jailene
$114 nightly
The price is $127
Feb 26 - Feb 27
Total with taxes and fees
Hampton Inn Westfield
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.

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 offers a range of activities including skiing, hiking, and exploring national and local parks, perfect for nature lovers.
  • Charming Downtown: Discover unique boutiques and cozy cafes in Winsted's vibrant downtown area, ideal for leisurely shopping and dining.
  • Historical Attractions: Visit stunning Victorian mansions and other historical sites that showcase the rich history of Winsted.
  • Romantic Getaways: The picturesque scenery makes Winsted an ideal destination for couples seeking a romantic retreat.
  • Diverse Accommodations: Enjoy a variety of lodging options, from pet-friendly hotels to family-oriented stays, ensuring a comfortable visit.

Find great hotels near Winsted

Winsted, Connecticut, offers a variety of hotel accommodations to suit every traveler. From pet-friendly options to family-oriented stays, you'll find the perfect place to relax after exploring the area's charm. Whether you’re seeking a business-themed environment or an agritourism experience, Winsted has it all. Discover the best hotels in the region with excellent reviews that cater to your preferences and make your visit memorable.

  • La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport: Nestled 20 miles from Winsted, La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport is the perfect choice for families and business travelers alike. This pet-friendly hotel welcomes furry companions, making it a great option for those traveling with pets. Business amenities include an accessible business center, ensuring you can stay productive during your stay. Families will appreciate the thoughtful children’s amenities, including free cribs and window guards for safety. With its warm atmosphere and convenient location, this hotel is designed to meet the diverse needs of all guests.
  • Homewood Suites by Hilton Hartford-Farmington: Located 19 miles from Winsted, Homewood Suites by Hilton Hartford-Farmington is a welcoming haven for LGBTQIA travelers and adventure seekers. This 3-star hotel offers a range of business facilities, including a 24-hour business center and conference space, making it an ideal spot for work-related trips. For those craving adventure, outdoor activities such as skiing, mountain biking, and kayaking are nearby. This hotel combines comfort with a commitment to inclusivity, ensuring all guests feel at home while enjoying their surroundings.
  • The Farmington Inn & Suites: Situated 18 miles from Winsted, The Farmington Inn & Suites offers a harmonious blend of business amenities and pet-friendly accommodations. With a 24-hour business center and multiple meeting rooms, it caters to the needs of business travelers while ensuring pets are welcome too. The hotel’s commitment to comfort and convenience makes it an excellent choice for those traveling with four-legged companions. Guests can enjoy the cozy ambiance and professional service, creating a satisfying stay for both work and leisure.

Where to stay in and around Winsted

Winsted, Connecticut, offers a delightful blend of outdoor adventures and charming scenery, perfect for a romantic getaway or family-friendly vacation. Explore the vibrant downtown area, where shopping enthusiasts can find unique boutiques and cozy cafes. Don't miss the picturesque recreational areas and stunning Victorian mansions that showcase the city's rich history. With its relaxing atmosphere, Winsted is an ideal destination to unwind and enjoy the beauty of New England.

  • Winchester: Nestled within the charming town of Winsted, Winchester is a lovely village that attracts visitors year-round. The area is known for its stunning outdoor scenery and romantic experiences, making it a popular spot for couples and nature enthusiasts. Peak travel times occur in April, July, and September, when outdoor activities like skiing and beach visits are in full swing. Nearby, you can explore national state parks and serene lakes, offering ample opportunities for hiking, fishing, and enjoying a peaceful day by the water.
  • West Hill Lake: Just 3 miles from Winsted, West Hill Lake is a picturesque village that draws visitors primarily in the summer months of July and August, as well as in October. Known for its breathtaking scenery and outdoor adventure options, this area is perfect for those seeking a romantic getaway or a family outing. With recreational areas and ski resorts nearby, you can enjoy activities like swimming, skiing, and hiking. The lake and surrounding beaches provide a perfect backdrop for relaxation and fun in the sun.
  • Pleasant Valley: Located 4 miles from Winsted, Pleasant Valley is a vibrant neighborhood that offers a unique blend of adventure and scenic beauty. Visitors flock here during the warmer months of July and August, as well as in October, to experience outdoor activities and discover local attractions. The area features shopping centers and malls, making it ideal for those looking to indulge in retail therapy. Nature lovers will appreciate the nearby river, waterfall, and national state park, perfect for hiking, picnicking, and enjoying the great outdoors.

Things to do in and around Winsted

Winsted, Connecticut, is perfect for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can enjoy activities like skiing at local ski fields, exploring scenic recreational areas, and discovering major attractions. With its beautiful landscapes, Winsted offers a variety of outdoor exploration opportunities and fun amusement parks, making it an ideal destination for a memorable vacation.

Shopping

The nearest shopping destination is Ames Plaza Shopping Center, just 1 mile from Winsted, offering a vibrant mix of entertainment and family-friendly options. If you're up for a drive, check out Rosedale Farms & Vineyards and Bloomfield Crossing, located 14 and 18 miles away, respectively, for unique finds.

Recreation

Satan's Kingdom State Recreation Area, located 7 miles from Winsted, offers serene hiking trails and peaceful picnic spots, perfect for wellness and relaxation. Music Mountain, 13 miles away, presents vibrant live performances, providing a delightful blend of entertainment and community spirit. Wintonbury Hills Golf Course, 16 miles out, combines sport with stunning outdoor views.

Adventure

Experience the thrill of skiing at Ski Sundown, located 7 miles from Winsted, where you can enjoy stunning slopes and a vibrant sports atmosphere. For motorsport enthusiasts, Lime Rock Park, 17 miles away, offers exhilarating races. Hike the Big Cathedral Trail, 14 miles from town, for breathtaking outdoor scenery.

Nightlife

In Winsted, Laurel Lanes offers fun arcade adventures for a lively night out. Just a short drive away, the Warner Theater and Infinity Music Hall and Bistro provide a blend of culture and entertainment, perfect for a romantic evening or family outing.

*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, consider visiting during the cheaper months of March or November to December, and aim to book your stay on a Monday for the best rates. Utilize Expedia's search tool to find budget-friendly hotels, and look for eco-certified options for sustainable stays. You can save even more by bundling your hotel, flights, and activities through an Expedia package deal. Additionally, join Expedia's One Key membership for exclusive discounts and earn OneKeyCash for future bookings.

  • 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: Expedia's intuitive search tool lets you specify your budget, desired location, and additional preferences. You can easily arrange your search results to display the lowest prices first, making it simple to find the most affordable hotel options. Additionally, you have the ability to refine your choices by hotel category—selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels available for booking.
  • Consider bundling your trip: You can save on costs by combining your hotel stay in Winsted with your flights and activities through an Expedia package deal.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions in and around Winsted

Winsted, Connecticut, is perfect for those seeking outdoor adventures and romantic getaways. With its stunning scenery, visitors can explore national parks, nature reserves, and local parks that offer eco-friendly experiences. Whether you're looking for thrilling activities or peaceful retreats, Winsted's attractions cater to all types of travelers eager to connect with nature.

  • Highland Lake: Nestled in Winsted, Highland Lake offers stunning scenery and a serene beach atmosphere, perfect for a romantic getaway or a relaxing day outdoors. Enjoy swimming, picnicking, or simply soaking in the natural beauty that surrounds you.
  • Burr Pond State Park: Located 4 miles from Winsted, this state park is a haven for adventure seekers. With picturesque trails and opportunities for hiking and fishing, Burr Pond State Park invites you to explore its breathtaking landscapes and enjoy outdoor activities.
  • Winchester Historical Society: Situated in Winsted, this history museum showcases the rich cultural heritage of the area. Discover fascinating exhibits that chronicle local history and immerse yourself in the stories that shape this charming community.

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

When visiting Winsted, Connecticut, you can fly into several major airports. Hartford, CT (BDL-Bradley Intl.) is 19 miles away and offers nearby accommodations like the DoubleTree by Hilton Hartford - Bradley Airport, just 1 mile from the airport, and the 4-star Marriott Hartford Downtown, located 12 miles away. Newburgh, NY (SWF-Stewart Intl.) is another option, situated 60 miles from Winsted, with hotels like The Dutchess Inn and Spa at Beacon, 6 miles away. Lastly, New Haven, CT (HVN-Tweed - New Haven Regional) is 46 miles distant, featuring hotels such as The Blake Hotel, only 3 miles from the airport.

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 $89 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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