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Compare 231 Vacation Homes in Winsted with updated reviews, rates, and availability.

Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (184)
"My husband and I had a very peaceful and relaxing long weekend at this lake house! It was very clean and has everything you need. We spent the majority of our time on the wonderful screened-in porch. The location was great and there was a little store/restaurant only a couple minutes walk up the street that was convenient and the food was really good! Overall, a great place to stay!"
Peace and quiet on the lake
Fridge, microwave, oven, stovetop
Newly Renovated Family House On Highland Lake with Dock
10.0 out of 10, Exceptional, (19)
"Amazing view. Great price. Great communication."
Newly Renovated Family House On Highland Lake with Dock
Outdoor dining
Charming 1870 cape cottage in Litchfield
10.0 out of 10, Exceptional, (21)
"The cottage house had a warm, welcoming vibe to it. It was very well maintained. The grounds were beautiful. The home had everything available that you could possibly want. It was very cozy. We had relatives from Italy with us and they absolutely loved it. I would definitely go back and I highly recommend it. Congratulations to the owners, because they have done a wonderful job with it."
Charming 1870 cape cottage in Litchfield
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Property grounds
Hilltown Nest is a wonderful place for family and friends to gather.
10.0 out of 10, Exceptional, (12)
"The entire property was spotlessly clean everywhere.Very well equipped. We didn’t even use the whole house it was so big. Comfortable beds, lots of towels, toilet roll, shampoo etc. Well equipped kitchen. Big grill, lovely terrace with table and lots of chairs. Nice fire pit. Basically everything you need for a perfect countryside getaway at a very reasonable price. Thank you very much."
Hilltown Nest is a wonderful place for family and friends to gather.
Fridge, microwave, stovetop, dishwasher
Litchfield County Getaway
10.0 out of 10, Exceptional, (35)
"Very nicely renovated house. Clean and comfortable. Well equipped kitchen. Large comfy living and dining room. Very responsive hosts. Only suggestion would be to provide a few more hooks in the bathrooms for guests to hang personal things (night clothes, used towels, etc.). I would highly recommended this place."
Litchfield County Getaway
Exterior
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, (4)
"We had a great time. Place is amazing. Highly recommend. We had four different families and we never felt cramped. Lovely open main room allowed us to stay connected. Bedrooms were nice and spacious, good bed options. Nice decor."
Quintessential 6-BR Berkshires Lodge
Fridge, microwave, oven, stovetop
Spacious three bedroom house near Historic Suffield Center. Pet Friendly!
10.0 out of 10, Exceptional, (2)
"It was wonderful! Enough room for everyone and everything was cozy and working. Appreciate the stay!"
The price is $300
$707 total
includes taxes & fees
Jun 13 - Jun 14
Spacious three bedroom house near Historic Suffield Center. Pet Friendly!
Property grounds
Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (120)
"Wonderful place! Thoughtfully decorated, clean and incredibly comfortable. Would rent again."
The price is $195
$363 total
includes taxes & fees
Jun 24 - Jun 25
Big farmhouse in the foothills of the Berkshires
Microwave, oven, stovetop, dishwasher
Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
10.0 out of 10, Exceptional, (2)
"My family and I enjoyed our stay here. We had lots of space for my 4yo to run around and each of my 3 kids had their own room. The house was very clean and the host was easily able to contact if I had questions or concerns. We would def. stay here again"
Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
Outdoor pool, a heated pool
Mountaintop Horse Farm with Heated Pool
10.0 out of 10, Exceptional, (15)
"Thank you for a lovely home to stay in during our family funeral weekend!"
Mountaintop Horse Farm with Heated Pool
Property grounds
Nature House Water View Large Deck 2 story Gazebo 2 bed 2 bath
10.0 out of 10, Exceptional, (6)
"excellent"
Nature House Water View Large Deck 2 story Gazebo 2 bed 2 bath
Fridge, microwave, oven, stovetop
Trout Brook Trail 2 · Sprawling Classic New England Home
10.0 out of 10, Exceptional, (10)
"The location was amazing! Although on a busy street, it was quiet and still a perfect walking distance from everything. Plenty of bars and restaurants just a few blocks away. The host was super easy to reach and the home was clean and well stocked with essentials."
Trout Brook Trail 2 · Sprawling Classic New England Home
Property grounds
Private Annex/Former Artist Studio
10.0 out of 10, Exceptional, (38)
"This charming 2-bedroom New Preston apartment was the perfect escape! Cozy rooms welcomed us with peace and comfort, melting away city stress. Host Melanie's warm smile and delicious homemade cookies added a personal touch that made our stay truly heartwarming. Reconnecting with nature was easy - breathtaking scenery, quiet streets, and a nearby lake offered peaceful beauty. This wasn't just a place to stay, it was an experience we'll treasure. Highly recommend! ⭐⭐⭐⭐⭐ P.S. too bad I forgot...
Private Annex/Former Artist Studio
Outdoor dining
Mountain View Getaway
10.0 out of 10, Exceptional, (36)
"We loved this property!!"
Mountain View Getaway
TV, DVD player
Peaceful, Post and Beam Loft, Sleeps 9
10.0 out of 10, Exceptional, (8)
"beautifully stay for couples."
Peaceful, Post and Beam Loft, Sleeps 9
Exterior
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
10.0 out of 10, Exceptional, (138)
"We had a great time! It was exactly how it looks in the pics. Amazing house and the views were great. Def going back again. Owner is very responsive. Everything was perfect"
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Exterior
Antique Farmhouse Totally Restored
10.0 out of 10, Exceptional, (79)
"There were 6 adults and 2 infants in our party, we were in town for our 25 year high school reunion. The house was incredible and the host went above and beyond to make sure we were well taken care of. This place is a hidden gem and deserves all of the praise."
Antique Farmhouse Totally Restored
Exterior
Tranquil 3-BR Waterfront Retreat
10.0 out of 10, Exceptional, (7)
"The house is immaculate! One of the cleanest properties we've stayed in. The house was the perfect size for my family of 4 (2 adults, 2 teens) with room for more. The beds are comfortable, and there were plenty of linens and towels. The linens and towels are high quality, very soft. The kids had fun fishing in the pond and made good use of the kayak (they caught some bass, pickerel and sun fish). The neighborhood is nice and quiet, dirt roads, no traffic...great for taking walks. We used the...
Tranquil 3-BR Waterfront Retreat
Fridge, microwave, oven, stovetop
Great Barrington Get Away
9.6 out of 10, Exceptional, (17)
"Nice, cozy, clean house with character. Great location as we could walk to town. Would stay again for sure."
Great Barrington Get Away
View from property
Private Berkshires Home On 5+ Acres, Rustic & Chic
10.0 out of 10, Exceptional, (2)
"The house was beautiful. It looked just like the pictures. The privacy and the beauty of the property made for such a serene vacation spot. The owners and property managers would respond immediately. I would definitely recommend this home. Love the Berkshires!"
Private Berkshires Home On 5+ Acres, Rustic & Chic
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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.

Other property types in Winsted

Property grounds
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
9.4 out of 10, Exceptional, (33)
"Very positive."
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Fridge, microwave, oven, stovetop
Newly Renovated Family House On Highland Lake with Dock
10.0 out of 10, Exceptional, (19)
"Amazing view. Great price. Great communication."
Newly Renovated Family House On Highland Lake with Dock
Fridge, microwave, oven, stovetop
Spacious three bedroom house near Historic Suffield Center. Pet Friendly!
10.0 out of 10, Exceptional, (2)
"It was wonderful! Enough room for everyone and everything was cozy and working. Appreciate the stay!"
The price is $300
$707 total
includes taxes & fees
Jun 13 - Jun 14
Spacious three bedroom house near Historic Suffield Center. Pet Friendly!
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.

Winsted Vacation Homes information

Number of reviews
678
Accommodation
231 Vacation Homes
Lowest Price
$195
Highest Price
$300

Recent reviews of Winsted hotels
Expedia verified reviews