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Vacation Homes in Winsted

Charming 1870 cape cottage in Litchfield

10.0 out of 10, Exceptional, (55)
"My family and I enjoyed our stay and their hospitality!"
Charming 1870 cape cottage in Litchfield

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

10.0 out of 10, Exceptional, (37)
"Our family had a wonderful stay at this beautiful home. It's well-equipped, clean and cozy and feels like you are out in the country but also a 10 minute drive from great restaurants, shops and skiing. We definitely plan to return."
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

10.0 out of 10, Exceptional, (9)
"I stayed with my mom and the 2 bedroom 1 bath was perfect for our stay. The house way cozy and in a quiet area. Would absolutely stay again; my mom is already talking about coming back to explore more of the surrounding areas!"
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

10.0 out of 10, Exceptional, (1)
"It's a wonderful house, lots of space to visit with family and the bed rooms were confortable and cozy. The host was very helpful and accesible at all times."
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Bluebird Valley Farmhouse

10.0 out of 10, Exceptional, (68)
"We stayed at the property while attending a family wedding. The house and yard were perfect. The best Vrbo we’ve ever stayed at. Would stay there again!"
Bluebird Valley Farmhouse

Prime West Hartford Center Location: Historic Gem

10.0 out of 10, Exceptional, (28)
"The house is very spacious, clean and comfortable. Will definitely book again!"
Prime West Hartford Center Location: Historic Gem

Peace and quiet on the lake

9.6 out of 10, Exceptional, (218)
"Comfortable home with amazing view. Enjoyed taking a walk around the lake (1 hour approx). Had an amazing dinner at Dream Away lodge which is 15 minutes away. "
Peace and quiet on the lake

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

10.0 out of 10, Exceptional, (27)
"Spacious, welcoming, so well stocked, we felt lucky to find the property."
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (54)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford

9.4 out of 10, Exceptional, (6)
"Beautiful new spacious property in a great safe neighborhood. Very nice for groups. Common Living space s conducive for gathering. Property still under construction as there were other homes still being built. Near busy street but monimal noise. Would stay again."
The price is ¥51,299
¥117,511 total
includes taxes & fees
Sep 11 - Sep 12
Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (139)
"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"
The price is ¥29,610
¥52,894 total
includes taxes & fees
Sep 7 - Sep 8
Big farmhouse in the foothills of the Berkshires

Spacious Home nestled along the Blackberry River in Northwest CT

10.0 out of 10, Exceptional, (86)
"The team stayed here for a curling tournament. Great location for that and perfect for 4 non-couple guests"
Spacious Home nestled along the Blackberry River in Northwest CT

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (39)
"We thoroughly enjoyed our stay and would go again. The host was easy to communicate with and answered our questions quickly. Hope we get to take advantage of the pretty backyard next time. "
The price is ¥35,088
¥73,260 total
includes taxes & fees
Sep 9 - Sep 10
Cheerful 3-bedroom cottage with woodstove

County Seat Colonial

10.0 out of 10, Exceptional, (11)
"This was just what we needed. Thank you for a beautiful home, adorable town and so much to do! Perfect weekend for my family!"
County Seat Colonial

NEW Beautiful Berkshires Farmhouse

NEW Beautiful Berkshires Farmhouse

Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB

10.0 out of 10, Exceptional, (2)
"Well, the title says it all beautiful rooms, beautiful furniture, great kitchen, tons of room wonderful outdoor space took advantage of the fire pit didn’t get a chance to go on the lake as we were on another lake, but all their amenities just looked amazing. I could spend a week they are easy will be back saw a beautiful dear "
Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB

Lakefront Fall Foliage in New England Just 2 Hours From NYC

10.0 out of 10, Exceptional, (80)
"Great place! Loved waking up to a water view. Very peaceful."
Lakefront Fall Foliage in New England Just 2 Hours From NYC

Charming Retreat at Stone Hill Estate – Nature Meets Luxury

10.0 out of 10, Exceptional, (2)
"Beautiful property and great location. A true retreat. "
The price is ¥59,220
¥105,338 total
includes taxes & fees
Sep 5 - Sep 6
Charming Retreat at Stone Hill Estate – Nature Meets Luxury

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

10.0 out of 10, Exceptional, (59)
"We were visiting University of Hartford and this was the perfect place to stay outside of the city. Great space with all the conveniences of home. Wonderful food options within walking distance. "
The price is ¥38,508
¥66,233 total
includes taxes & fees
Sep 7 - Sep 8
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi

10.0 out of 10, Exceptional, (1)
"Clean and quiet location, great place for a relaxing stay."
Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi
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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Top Winsted Hotel Reviews

Find out more about Winsted

Find out more about Winsted

Winsted Vacation Homes information

Number of reviews
Accommodation
316 Vacation Homes
Lowest Price
¥29,610
Highest Price
¥59,220