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Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

Compare 314 Vacation Homes in Winsted with updated reviews, rates, and availability.

Stylish & Luxurious 3 BDR Home with Play Station
Fridge, microwave, oven, stovetop

Stylish & Luxurious 3 BDR Home with Play Station

9.4 out of 10, Exceptional, (9)
"We needed a place for our family of 6 to stay while visiting family in the area. This place was exactly what we needed, as advertised, and the owner was quick with communications. We would definitely stay here again!"
Stylish & Luxurious 3 BDR Home with Play Station
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Exterior

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

10.0 out of 10, Exceptional, (149)
"The location is beautiful and there are lots of places to visit in the area. The house is nice; great view of Otis Reservoir. It took us a while to figure out the multiple thermostats, but it was a good Christmas house. The owner was nice enough to allow us to have a Christmas tree, and had someone make an extra trash pick up for us after Christmas.The one thing we were disappointed in was the cleanliness. Shower curtains were moldy, some of the dishes weren't very clean, expired condiments...
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Lakefront Cottage - Hot Tub, Game Room & Scenic Views
Outdoor spa tub

Lakefront Cottage - Hot Tub, Game Room & Scenic Views

10.0 out of 10, Exceptional, (3)
"Everything was great. "
The price is SAR 770
SAR 1,463 total
includes taxes & fees
21 Apr - 22 Apr
Lakefront Cottage - Hot Tub, Game Room & Scenic Views
Mountain View Getaway
Outdoor dining

Mountain View Getaway

10.0 out of 10, Exceptional, (50)
"From the moment we walked into this house , we were wowed. The incredible picturesque views that streamed in through all the wi dies in the house made us feel like we were enveloped by nature. We were able to enjoy sunsets and sunrises from the panoramic windows and the house itself was exceptionally clean, had quality appliances and everything g we would need to prepare meals. Karen and Larry, our hoses, were extremely responsive and accommodating. There were beautiful roses, snacks and...
Mountain View Getaway
Spectacular views and close to Great Barrington.
Smart TV, fireplace

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (213)
"Beautiful house in idyllic setting. Great host- we’ll be back!"
Peace and quiet on the lake
Tranquil Litchfield Connecticut Retreat".
Property grounds

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (10)
"My friends and stayed for a night. The house is nice and the owners is very communicative. "
The price is SAR 826
SAR 1,174 total
includes taxes & fees
27 Apr - 28 Apr
Tranquil Litchfield Connecticut Retreat".
The Race Mountain House
Pool

The Race Mountain House

2.0 star property
10.0 out of 10, Exceptional, (1)
"We loved everything about the house - it was in a great location and perfect for a weekend away with friends!"
The Race Mountain House
Cheerful 3-bedroom cottage with woodstove
Property grounds

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (35)
"The property was centrally located for skiing, and was a comfortable stay."
The price is SAR 702
SAR 1,656 total
includes taxes & fees
13 May - 14 May
Cheerful 3-bedroom cottage with woodstove
Owl's Nest - Cozy Westfield Home w/ Fire Pit
Fridge, microwave, oven, stovetop

Owl's Nest - Cozy Westfield Home w/ Fire Pit

9.0 out of 10, Wonderful, (4)
"We were really only at the house for the late evenings, nights, and mornings. We found the kitchen well stocked to make breakfast (we bought the groceries). The beds were comfortable. Only a couple minor issues that we just handled. The temperature control was preprogrammed to go to 50 degrees in the evening and overnight. We couldn't seem to reprogram it; however, did get it to kick up warmer about midnight or so. The shower in the main floor bathroom was hard to get turned off so the...
Owl's Nest - Cozy Westfield Home w/ Fire Pit
Perfect Nature Retreat In Great Barrington
Exterior

Perfect Nature Retreat In Great Barrington

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a great time at the house. We had everything we needed. It was close to town. The space is very comfortable."
Perfect Nature Retreat In Great Barrington
Hilltown Nest is a wonderful place for family and friends to gather.
Property grounds

Hilltown Nest is a wonderful place for family and friends to gather.

9.8 out of 10, Exceptional, (15)
"Sadly we were only here for a couple of nights, but this place was very nice. I manage vacation rentals myself and i was very impressed by the cleanliness of this place, especially considering the size of it. The house is great for a family with lots of room to spread out. Our grandkids enjoyed tinkling on the piano and playing in the backyard. Would definitely choose to stay here again!"
Hilltown Nest is a wonderful place for family and friends to gather.
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Interior

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (19)
"Very nice clean house. Felt like coming home after work"
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Interior

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

2.0 star property
10.0 out of 10, Exceptional, (2)
"Same day check in info, not provided the day before like most hosts "
The price is SAR 1,471
SAR 3,079 total
includes taxes & fees
5 May - 6 May
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Quintessential 6-BR Berkshires Lodge
Exterior

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for us. Spacious, clean, comfortable. Beds comfortable. Bathrooms really nice. The road in the development is dirt, a 4wd is needed as stated. It was muddy and rutty on arrival, then snow and ice , but do-able. Great house. Would recommend "
Quintessential 6-BR Berkshires Lodge
The Goshen Glass Chalet
Outdoor dining

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (33)
"Great place. Really enjoyed staying there"
The Goshen Glass Chalet
Home in Great Barrington
Fridge, microwave, oven, stovetop

Home in Great Barrington

9.6 out of 10, Exceptional, (19)
"Our family had a wonderful experience and stay. "
The price is SAR 826
SAR 1,262 total
includes taxes & fees
12 May - 13 May
Home in Great Barrington
Historic Farmhouse Near Mountains & Colleges!
Fridge, microwave, stovetop, dishwasher

Historic Farmhouse Near Mountains & Colleges!

10.0 out of 10, Exceptional, (7)
"Lovely, spacious farmhouse. Well appointed and comfortable. Highly recommend. "
Historic Farmhouse Near Mountains & Colleges!
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, (53)
"This property is a perfect place to gather family or friends. Its beautifully appointed bedrooms and study gave individual family members space for privacy and one-on-one conversations, and its three large and elegant spaces--living room, dining room, and kitchen/family room--allowed all of us to gather for games, conversations, and meals. Because we stayed Christmas week we couldn't take advantage of the property's gorgeous outdoor spaces, but Lauren provided us with a decorated Christmas tree...
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Lakeside 5-BR Home in Idyllic Berkshires
TV, fireplace, offices

Lakeside 5-BR Home in Idyllic Berkshires

10.0 out of 10, Exceptional, (1)
Lakeside 5-BR Home in Idyllic 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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Other property types in Winsted

The Cottage at Highland Lake, year-round, waterfront with a boat dock
Beach nearby, sun loungers, beach towels

The Cottage at Highland Lake, year-round, waterfront with a boat dock

10.0 out of 10, Exceptional, (4)
"Jeanne was wonderful to work with and very responsive when we booked our last minute get away. Location is ideal - we brought our kayaks and very easy launching area. Would definitely not hesitate to come back to the same spot. Thanks for sharing your home with us. "
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
Beach

Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!

10.0 out of 10, Exceptional, (92)
"The spacious house and view of the frozen lake were wonderful for our family gathering. It was unfortunate the hot tub was broken and there were some water issues, but the hostess was gracious in trying to accommodate us. "
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Food and drink

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (19)
"A great winter getaway in the Berkshires. We loved the location of this very nice spot in Great Barrington. Had some great dinners we could walk to and we were able to do amazing hikes during the day and visit other spots around GB as well. Would definitely recommend! House is clean and has a nice vibe and beds comfortable. Nice shower too!"
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
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.