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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
The price is £90
includes taxes & fees
23 Feb - 24 Feb
Locust Tree Bed and Breakfast LLC

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (824 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
Monument Mountain Motel

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (192 reviews)
"Clean room, great staff"
United States
Tamiya
The price is £111
includes taxes & fees
1 Mar - 2 Mar
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
The price is £115
includes taxes & fees
23 Feb - 24 Feb
Truman Gillet House Bed & Breakfast

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (571 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is £62
includes taxes & fees
23 Feb - 24 Feb
Travelodge by Wyndham Great Barrington Berkshires

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, (1,174 reviews)
"Always my go to hotel when I come home for visits, friendly staff, clean hotel. "
United States
Kathleen
The price is £88
includes taxes & fees
2 Mar - 3 Mar
Holiday Inn Express & Suites Bradley Airport by IHG

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very good, (1,004 reviews)
"Clean room, great location"
United States
Andrea
The price is £55
includes taxes & fees
23 Mar - 24 Mar
Quality Inn Great Barrington

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.2 out of 10, Very good, (16 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
The price is £129
includes taxes & fees
24 Feb - 25 Feb
The Millerton Inn

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
The price is £166
includes taxes & fees
23 Feb - 24 Feb
The Berkshire Mountain Inn

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (828 reviews)
"I will stay again"
United States
Jailene
The price is £89
includes taxes & fees
1 Mar - 2 Mar
Hampton Inn Westfield

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
The price is £149
includes taxes & fees
1 Mar - 2 Mar
Wilder House 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
The price is £91
includes taxes & fees
23 Feb - 24 Feb
The Little Lion

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (917 reviews)
"Staff was very friendly. Everything was clean and well kept. Small hotel but very cozy and quiet."
United States
Gloria
The price is £77
includes taxes & fees
11 Mar - 12 Mar
Quality Inn Westfield - Springfield

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington
2.5 star property
Farmington
8.0 out of 10, Very good, (1,004 reviews)
"Great deal in the Hartford area. Large room, comfy bed and super nice people. Very convenient to I 95"
United States
Patricia
The price is £69
includes taxes & fees
23 Feb - 24 Feb
Extended Stay America Suites Hartford Farmington

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 friendly, room was clean. Overall great stay, thanks!"
United States
Nathaniel
The price is £78
includes taxes & fees
16 Mar - 17 Mar
Days Inn by Wyndham Torrington

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, (736 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is £86
includes taxes & fees
26 Feb - 27 Feb
Holiday Inn Express Hotel & Suites Great Barrington by IHG

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (38 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is £99
includes taxes & fees
20 Mar - 21 Mar
East Rock Inn

The Farmington Inn & Suites

The Farmington Inn & Suites
3.0 star property
Farmington
8.8 out of 10, Excellent, (1,004 reviews)
"This place is like a warm hug from your favorite auntie. "
United States
kieran
The price is £102
includes taxes & fees
26 Feb - 27 Feb
The Farmington Inn & Suites

The Abner Hotel

The Abner Hotel
3.0 star property
Litchfield Historic District
9.4 out of 10, Exceptional, (51 reviews)
"My stay was flawless. From staff to the clean room and comfortable bedding all made for an amazing experience."
United States
Francis
The Abner Hotel

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, (767 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is £133
includes taxes & fees
26 Feb - 27 Feb
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.

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

Top Winsted Hotel Reviews

More cheap stays in Winsted

Find out more about Winsted

Top reasons to visit Winsted

  • Outdoor Adventures: Winsted is perfect for outdoor enthusiasts, offering activities like skiing and hiking in stunning national parks.
  • Picturesque Lakes: Explore the beautiful lakes that provide a serene backdrop for relaxation and eco-friendly adventures.
  • Charming Atmosphere: The quaint charm of Winsted makes it ideal for romantic getaways and family outings.
  • Diverse Accommodation: Options range from cosy inns to comfortable hotels, catering to all types of travellers.
  • Local Attractions: Discover nearby towns filled with recreational opportunities and unique local charm.

Find great hotels near Winsted

Discover the charm of Winsted, Connecticut, where a variety of lodging options await you. From inviting inns to comfortable hotels, there’s something for every traveller. Whether you’re seeking pet-friendly accommodations, a business-themed stay, or an adventure-filled getaway, Winsted's hotels offer a welcoming experience tailored to your needs. Explore the best hotels and inns in the area to make your vacation truly memorable.

  • La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport: Experience a warm and welcoming atmosphere at La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport. Located approximately 12.4km from Winsted, this hotel is ideal for those seeking a business-themed getaway. With a strong commitment to inclusivity, the property is LGBTQIA-friendly and pet-friendly, ensuring a comfortable stay for all. Business travellers will appreciate the well-equipped Business Centre and accessible facilities. Pets are permitted with specific policies in place, making it a great choice for those travelling with furry companions.
  • Homewood Suites by Hilton Hartford-Farmington: Nestled around 11.8km from Winsted, Homewood Suites by Hilton Hartford-Farmington offers a perfect blend of adventure and comfort. This pet-friendly and LGBTQIA-friendly hotel is designed for the active traveller, featuring a variety of nearby adventure sports and recreation activities, including skiing, hiking, and kayaking. Guests can enjoy spacious suites with fully equipped kitchens, ideal for long stays. The hotel’s commitment to providing a welcoming and adventurous experience makes it an excellent choice for those looking to explore the great outdoors.
  • The Farmington Inn & Suites: Located just 11.2km from Winsted, The Farmington Inn & Suites provides a sophisticated environment for business travellers. This pet-friendly hotel features a 24-hour Business Centre and multiple meeting rooms, making it perfect for corporate events. The property is LGBTQIA-friendly, ensuring a welcoming atmosphere for everyone. Guests can expect comfortable accommodations with modern amenities designed for productivity and relaxation. With a focus on meeting the needs of business travellers, it's an excellent option for your stay in the area.

Where to stay in and around Winsted

Winsted, Connecticut, offers a delightful escape for those seeking outdoor adventures and picturesque scenery. With its charming atmosphere, perfect for family-friendly outings or romantic getaways, Winsted invites you to explore nearby towns filled with recreational opportunities. Make the most of your visit during the warmest months and discover the enchanting beauty of Winchester and its surroundings, ensuring a memorable holiday experience.

  • Winchester: Nestled in the heart of Winsted, Winchester is a delightful village that offers a serene escape for those seeking natural beauty and outdoor adventures. The area experiences a moderate influx of visitors, particularly in April, July, and September. Travellers flock here for its picturesque scenery and romantic atmosphere, making it ideal for couples and nature enthusiasts alike. Popular activities include skiing at nearby resorts and enjoying the tranquil lakes and beaches. With a national state park close by, Winchester is perfect for hiking and exploring the great outdoors.
  • West Hill Lake: Located a mere 1.9km from Winsted, West Hill Lake is a charming village that invites visitors year-round but sees peak travel during July to August and October. This destination is renowned for its stunning landscapes and recreational opportunities. Visitors can indulge in various outdoor activities, including skiing and relaxing at the local beach. The area’s national state park provides a perfect backdrop for hiking, picnicking, and enjoying the serene lake views. West Hill Lake is an excellent choice for those seeking romance and adventure in a peaceful setting.
  • Riverton: Just 2.5km from Winsted, Riverton is a vibrant city that attracts visitors throughout the year, particularly in the summer months of July and August. Known for its scenic beauty and outdoor activities, Riverton offers a plethora of options for recreation, including golf courses and private country clubs. The city is situated near stunning lakes and rivers, making it ideal for fishing and boating. With its proximity to a national state park, Riverton is a great spot for hiking and enjoying nature, perfect for a romantic getaway or a family adventure.

Things to do in and around Winsted

Winsted offers a delightful escape for those seeking outdoor adventures and scenic beauty. Visitors can enjoy activities such as skiing at local ski fields and exploring recreational areas, making it an ideal destination for a romantic getaway or a fun-filled vacation. Whether you're hitting the slopes or taking in the stunning landscapes, Winsted provides a charming backdrop for memorable experiences.

Shopping

In Winsted, you can enjoy shopping at Ames Plaza Shopping Center, just 621m away, offering a lively mix of businesses and family-friendly entertainment. Additionally, Ledgebrook Plaza provides a great shopping experience nearby. If you're up for a drive, Rosedale Farms & Vineyards is located 8.7km away, perfect for unique gifts.

Recreation

At Satan's Kingdom State Recreation Area, immerse yourself in nature with serene hiking trails and tranquil picnic spots just 4.3km from Winsted. Enjoy live performances at Music Mountain, 8.1km away, where the vibrant atmosphere enhances your cultural experience. For outdoor sports, Wintonbury Hills Golf Course, 9.9km distant, offers a stunning golfing experience.

Adventure

Experience the thrill of motor racing at Lime Rock Park, located 10.6km from Winsted, where the adrenaline of speed and competition fills the air. For winter fun, Ski Sundown, a ski field 4.3km away, offers exhilarating slopes and a vibrant sports atmosphere. Explore the Big Cathedral Trail, 8.7km away, for a scenic hike surrounded by nature's beauty.

Nightlife

In Winsted, Laurel Lanes offers a lively arcade adventure experience perfect for families. Just 5.6km away, Warner Theater and Infinity Music Hall and Bistro provide captivating entertainment and cultural experiences, ideal for a romantic night out or a fun family evening.

Booking tips and Expedia advantages for Winsted

For a budget-friendly trip to Winsted, consider visiting during the cheaper months of March and November to December, with Monday being the most affordable day to book. Avoid visiting in the peak summer months of July and August, as well as October. Utilise Expedia’s search tool to filter options by budget and location, and take advantage of package deals that combine flights and hotels for extra savings. Look out for great deals on hotels and inns to maximise your savings while enjoying the 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: Utilise Expedia’s search tool to refine your preferences, such as your budget, desired location, and preferred hotel type. To discover the most affordable prices and offers, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel reservation in Winsted with your flights and activities through an Expedia package deal.

Find the best attractions in and around Winsted

Winsted, Connecticut, is an idyllic destination for outdoor enthusiasts and those seeking a romantic getaway. Visitors can explore stunning national parks, nature reserves, and picturesque lakes, making it perfect for eco-friendly adventures. The area offers a variety of attractions that cater to travellers looking to immerse themselves in the beautiful scenery and enjoy a range of activities. Don't miss the opportunity to discover the local charm and natural beauty that Winsted has to offer.

  • Enders State Forest: Located 6.2km from Winsted, this picturesque forest offers a tranquil escape into nature. Enjoy hiking trails, diverse wildlife, and the thrill of outdoor adventures amidst the serene backdrop of lush greenery.
  • Highland Lake: Situated within Winsted, Highland Lake is perfect for a romantic day out. With its lovely beach and stunning scenery, visitors can enjoy activities such as swimming, kayaking, or simply relaxing by the water’s edge.
  • Northwestern Connecticut Community College: Also within Winsted, this college embodies the region's cultural vibe. Explore its vibrant campus, attend events, or appreciate local art, making it a unique educational and cultural stop.

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 LowSlightly Low
February27.1°F (-2.7°C)Light RainMostly CloudyAverageSlightly Low
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 HighSlightly High
July71.6°F (22.0°C)Light RainMostly SunnySlightly HighSlightly High
August69.6°F (20.9°C)Light RainMostly SunnyAverageAverage
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 LowAverage

The nearest major airports for your trip to Winsted

When visiting Winsted, Connecticut, the nearest major airport is Hartford, CT (BDL-Bradley International), located 11.8km away. Recommended hotels nearby include the DoubleTree by Hilton Hartford - Bradley Airport, a 4-star hotel just 621m from the airport, and the Marriott Hartford Downtown, which is 7.5km away. Another option is the Simsbury 1820 House, a charming 4-star bed & breakfast situated 4.3km from the airport. Additionally, New Haven, CT (HVN-Tweed - New Haven Regional) is 28.6km away, with excellent accommodations such as the Omni New Haven Hotel at Yale and Graduate by Hilton New Haven, both only 1.9km from the airport.

Frequently asked questions

What is the best area to stay in Winsted?
The best area to stay in Winsted is generally around the town centre, particularly near Main Street and the surrounding streets.

This area provides easy access to Winsted's local amenities. You'll find a selection of local shops, eateries, and services along Main Street, which runs through the heart of the town. The town green is a central feature, offering a pleasant open space.

For travellers looking for convenience and a central base to explore the Litchfield Hills, staying near the town centre is ideal.
What are the best family hotels in Winsted?
For family-friendly accommodation in Winsted, Rock Hall Luxe Lodging is an excellent option.

This 4.5-star hotel, with an outstanding 10.0 rating, is highly regarded by families. Guests appreciate the complimentary breakfast, including full breakfast options, and the convenience of free wired internet in public areas. The availability of free rollaway extra beds makes it particularly suitable for families travelling with children, and free self-parking adds to the ease of your stay.
What are the best spa hotels in Winsted?
For a top-rated spa hotel in Winsted, Rock Hall Luxe Lodging is an exceptional choice.

This 4.5-star hotel boasts an outstanding 10.0 rating and offers a superb on-site spa, great for relaxation and rejuvenation. Guests also benefit from complimentary breakfast, including a full breakfast option, and free wired internet access in public areas. Additionally, self-parking is provided at no extra cost, adding to the convenience of your stay.
What hotels in Winsted offer free breakfast?
For hotels in Winsted offering a complimentary breakfast, Rock Hall Luxe Lodging is an excellent choice.

This 4.5-star hotel, with an outstanding 10.0 rating, provides a free full breakfast daily, ensuring a great start to your day. Guests also benefit from complimentary wired internet in public areas and free self-parking. The hotel features air conditioning, premium bedding, and a fireplace in its rooms, along with designer toiletries. For recreation, there is outdoor tennis available on-site.
What are the most romantic hotels in Winsted for couples?
For a romantic stay in Winsted, couples should consider Rock Hall Luxe Lodging.

This 4.5-star accommodation boasts an exceptional 10.0 rating and offers a truly luxurious experience. Each room features premium bedding and a fireplace, creating a cosy and intimate setting. Guests can enjoy complimentary breakfast, including a full breakfast, and free wired internet in public areas. The property also provides free self-parking and amenities like air conditioning and designer toiletries. For relaxation, there is a hot tub available, and some rooms even include a private balcony. Additionally, guests can enjoy outdoor tennis on site.
When is the best time to go to Winsted?
The best time to go to Winsted is during the late spring, summer, and early autumn months, from May to October, when the weather is most pleasant for outdoor activities.

May and June offer mild temperatures, generally ranging from 10°C to 25°C, making it ideal for exploring the natural beauty of the surrounding Litchfield Hills. This period is particularly good for hiking on trails like those around Burr Pond State Park or enjoying a gentle stroll through the town's historic areas before the peak summer heat.

July and August are the warmest months, with temperatures often between 20°C and 30°C. This is superb for enjoying Winchester Lake, whether it's for fishing, kayaking, or simply relaxing by the water. The local farmers' markets are also in full swing during this time, offering fresh produce and a chance to experience local life.

September and October bring cooler temperatures, typically from 8°C to 20°C, and the spectacular display of autumn foliage. This is a popular time for scenic drives through the countryside, visiting local cider mills, and enjoying outdoor festivals.
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?
Members always get our best prices. Find our best Winsted hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
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 £64 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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