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Holiday Homes in Winsted

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Check prices for these dates

Next weekend
26 Sept - 28 Sept
In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov

Featured Holiday Homes in Winsted and around

Charming 1870 cape cottage in Litchfield
Pool

Charming 1870 cape cottage in Litchfield

10.0 out of 10, Exceptional, (57)
"My family and I enjoyed our stay and their hospitality!"
Charming 1870 cape cottage in Litchfield
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Fridge, microwave, oven, stovetop

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

10.0 out of 10, Exceptional, (37)
"We had the most wonderful trip! The location is perfect - easy access to downtown GB but still very relaxing and private. The kitchen is beautifully equipped and we ended up cooking most of our meals there. And the living room/great room led to hours of conversation. Can't wait to come back for a longer stay."
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Bluebird Valley Farmhouse
Property grounds

Bluebird Valley Farmhouse

10.0 out of 10, Exceptional, (69)
"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
Cheerful 3-bedroom cottage with woodstove
Property grounds

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (39)
"The property was centrally located for skiing, and was a comfortable stay."
The price is €428
includes taxes & fees
13 Oct - 14 Oct
Cheerful 3-bedroom cottage with woodstove
Prime West Hartford Center Location: Historic Gem
Fridge, microwave, oven, stovetop

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
Lakefront Fall Foliage in New England Just 2 Hours From NYC
Interior

Lakefront Fall Foliage in New England Just 2 Hours From NYC

10.0 out of 10, Exceptional, (81)
"Wonderful time, beautiful lakeside view"
Lakefront Fall Foliage in New England Just 2 Hours From NYC
Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford
Fridge, microwave, oven, stovetop

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

9.2 out of 10, Wonderful, (7)
"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 €496
includes taxes & fees
22 Sept - 23 Sept
Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Smart TV, fireplace, DVD player

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!
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Exterior

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

9.8 out of 10, Exceptional, (20)
"We had a wonderful time, the property is lovely and the house is delightful."
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Whispering Estate Guest House - A Romantic Countryside Getaway
Exterior detail

Whispering Estate Guest House - A Romantic Countryside Getaway

10.0 out of 10, Exceptional, (2)
"Beautiful property and great location. A true retreat. "
The price is €1,035
includes taxes & fees
21 Sept - 22 Sept
Whispering Estate Guest House - A Romantic Countryside Getaway
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Outdoor dining

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

10.0 out of 10, Exceptional, (10)
"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
Big farmhouse in the foothills of the Berkshires
Property grounds

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 €315
includes taxes & fees
28 Sept - 29 Sept
Big farmhouse in the foothills of the Berkshires
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (55)
"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!
The Meadows House @ Otis Ridge w/ 7-person hot tub
Outdoor spa tub

The Meadows House @ Otis Ridge w/ 7-person hot tub

9.6 out of 10, Exceptional, (37)
"We had a lovely time. Peaceful and cozy house, great private hot tub"
The Meadows House @ Otis Ridge w/ 7-person hot tub
Linny's Lakeview Cottage - Cozy, fun & updated
Fridge, microwave, oven, stovetop

Linny's Lakeview Cottage - Cozy, fun & updated

10.0 out of 10, Exceptional, (62)
"Very great location, close to my family. Great spot!!"
Linny's Lakeview Cottage - Cozy, fun & updated
Spacious Home nestled along the Blackberry River in Northwest CT
Fridge, microwave, oven, stovetop

Spacious Home nestled along the Blackberry River in Northwest CT

10.0 out of 10, Exceptional, (86)
"House was great, lots of space and very clean, Had everything we needed. The host was terrific- We will definitely be staying again."
Spacious Home nestled along the Blackberry River in Northwest CT
Private Lakefront Home w/ Private Lake, 3 Bedrooms - Minutes to Hotchkiss
Interior

Private Lakefront Home w/ Private Lake, 3 Bedrooms - Minutes to Hotchkiss

2.0 star property
Private Lakefront Home w/ Private Lake, 3 Bedrooms - Minutes to Hotchkiss
Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB
Fridge, microwave, oven, stovetop

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
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (60)
"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 €386
includes taxes & fees
21 Sept - 22 Sept
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
The Goshen Glass Chalet
Outdoor dining

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (40)
"we couldn't ask for a better place. It had all the conveniences we like. The host did a great job here."
The Goshen Glass Chalet
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

Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport

10/10 Excellent
"It was extremely convenient since the car rentals are closed when we get in. Shuttle to the hotel, and back the next day to the airport for car rental. Very easy. Good breakfast too."
Judi 1-night trip
Posted 3 days ago
Hampton Inn Hartford/Airport

Find out more about Winsted

Find out more about Winsted

Winsted Holiday Homes information

Number of reviews
845
Accommodation
319 Holiday Homes
Lowest Price
€315
Highest Price
€1,035

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