Photo by Kim Knox Beckius

Holiday Homes in Winsted

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Featured Holiday Homes in Winsted and around

Cheerful 3-bedroom cottage with woodstove
Property grounds
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (26)
"Impeccably clean, wonderful owner, kitchen with everything, strong WiFi, luxurious master bath. "
The price is €464
includes taxes & fees
21 Oct - 22 Oct
Cheerful 3-bedroom cottage with woodstove
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, (141)
"Perfect home on Otis Lake with plenty of room for a group of friends to gather. Kitchen was fully stocked with all the utensils, pots/pans, dishes to make a nice meal. Beds were very comfortable. Plenty of outdoor furniture to gather near the fire pit by the lake. Keurig coffee maker available to make coffee in the morning. Nice and quiet, felt very private. Plenty of room for parking. Thanks for letting us rent."
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Charming 1870 cape cottage in Litchfield
Outdoor dining
Charming 1870 cape cottage in Litchfield
10.0 out of 10, Exceptional, (31)
"Beautiful house"
Charming 1870 cape cottage in Litchfield
Peace and quiet on the lake
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (190)
"Loved it!"
Peace and quiet on the lake
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.
Trout Brook Trail 2 · Sprawling Classic New England Home
Fridge, microwave, oven, stovetop
Trout Brook Trail 2 · Sprawling Classic New England Home
10.0 out of 10, Exceptional, (15)
"We had a great time in the home. My family of 5 stayed to explore the area. We were central to everything. There was a slight delay entering the property that was resolved very quickly and with no issue. Mark was very responsive. The home itself was very acclectic and fun. We felt very comfortable there. It was also stocked with many thoughtful items such as bottled water, ear plugs, books, etc. to help make our stay comfortable. It was a short walk to several blocks of amenities in West...
Trout Brook Trail 2 · Sprawling Classic New England Home
Westfield Vacation Rental w/ Porch, Pets Welcome!
Exterior
Westfield Vacation Rental w/ Porch, Pets Welcome!
2.0 star property
2.0 out of 10, (1)
"The house looked like an abandoned property. It was dirty and gross. The sheets had hair on them. We actually couldn't stay. We were hopeful that after taking pictures and sending them, we have some sort of recoupment but we did not. Even though we booked through vrbo, it was apparently another company's listing and they were also no help. We won't use vrbo again. Also watch out for Evelve,"
Westfield Vacation Rental w/ Porch, Pets Welcome!
Pristine Home In Becket Woods
Fridge, microwave, oven, stovetop
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (9)
"Near Jacob's Pillow!"
Pristine Home In Becket Woods
Big farmhouse in the foothills of the Berkshires
Property grounds
Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (127)
"We planned a family reunion in the area. The farm house was pet friendly and the perfect location to our family that lived 20 minutes away. Eric was very accommodating. It was quiet and relaxing."
The price is €355
includes taxes & fees
23 Sept - 24 Sept
Big farmhouse in the foothills of the Berkshires
Cozy Lakefront Bungalow w firepit/dock/kayaks
Terrace/patio
Cozy Lakefront Bungalow w firepit/dock/kayaks
10.0 out of 10, Exceptional, (23)
"This is our second time visiting the area and staying at this beautiful home. It's close to many activities for children and adults, easy to access food and services and a beautiful overall area and home. We truly enjoy visiting!"
Cozy Lakefront Bungalow w firepit/dock/kayaks
Ranch on 5+ acres & 0.7 mi to GB Main St. Sleeps 10 + Wi-Fi + HOT TUB
Property grounds
Ranch on 5+ acres & 0.7 mi to GB Main St. Sleeps 10 + Wi-Fi + HOT TUB
10.0 out of 10, Exceptional, (16)
"House was fantastic—clean, comfortable, and in a great location. Alyssa was always available by text and cheerfully helped us deal promptly with a couple of minor hiccups while we were there. We have already rebooked for next year!"
Ranch on 5+ acres & 0.7 mi to GB Main St. Sleeps 10 + Wi-Fi + HOT TUB
Mountain View Getaway
Outdoor dining
Mountain View Getaway
10.0 out of 10, Exceptional, (41)
"This is our second year staying with at Karen and Larry’s property and it did not disappoint. They are incredible hosts and their home is conveniently located near the Lime Rock Track (less than 3 miles). It’s a beautiful and peaceful setting and extremely comfortable home. We highly recommend."
Mountain View Getaway
The Meadows House @ Otis Ridge w/ 7-person hot tub
Property grounds
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, (24)
"the Meadows House was very comfortable. Now that there are more grandchildren than children we have outgrown our families lake house. The local hotels are never comfortable for our tall family. The Meadows house was perfect. Beautiful views I wish we had been able to enjoy the hot tub but it was a beautiful week and the lake was calling. we would stay at the Meadow House again. The host was very attentive and checked in (via text)during our stay which was nice."
The Meadows House @ Otis Ridge w/ 7-person hot tub
Quintessential 6-BR Berkshires Lodge
Exterior
Quintessential 6-BR Berkshires Lodge
9.8 out of 10, Exceptional, (7)
"Nice. Quiet. The new pool is very nice."
Quintessential 6-BR Berkshires Lodge
Antique Farmhouse Totally Restored
Exterior
Antique Farmhouse Totally Restored
10.0 out of 10, Exceptional, (82)
"We had 15 people stay for three nights for a family reunion - 9 adults and 6 kids. The house worked well, as all had reasonably private spaces. The countryside is beautiful. Visits to a lake for swimming and several local waterfalls worked well for all."
Antique Farmhouse Totally Restored
Family House On Highland Lake with Dock
Fridge, microwave, oven, stovetop
Family House On Highland Lake with Dock
10.0 out of 10, Exceptional, (23)
"Stayed for labor day with family from out of state. Plenty of room for 4 adults and 4 kids, Could have easily fit more. Had a great time on the dock and having fires in the back yard. "
Family House On Highland Lake with Dock
Massive 5 Bedrooms: 3King 2Queen
Fridge, microwave, oven, stovetop
Massive 5 Bedrooms: 3King 2Queen
9.2 out of 10, Wonderful, (5)
"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 €626
includes taxes & fees
1 Oct - 2 Oct
Massive 5 Bedrooms: 3King 2Queen
Waterview Home in the Berkshires: Near Hiking
Outdoor dining
Waterview Home in the Berkshires: Near Hiking
9.4 out of 10, Exceptional, (19)
"My partner and I had a lovely stay for our visit to the Berkshires. The house was the perfect place to relax and unwind after a day exploring the area. The location is ideal with plenty of shops near by for essentials but still felt secluded. We hope to come back soon!"
Waterview Home in the Berkshires: Near Hiking
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Fridge, microwave, oven, stovetop
Charming 3BR Hilltop House, Newly Remodeled with Arcade
10.0 out of 10, Exceptional, (16)
"Clean, Cozy and Comfortable "
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Private Cabin On Over 12 Acres Of Woods!
Fridge, microwave, oven, stovetop
Private Cabin On Over 12 Acres Of Woods!
9.6 out of 10, Exceptional, (4)
"The property was perfect for our weekend in Becket. The house was very comfortable and the grounds quite beautiful. We enjoyed our visit."
Private Cabin On Over 12 Acres Of Woods!
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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.
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Other property types in Winsted

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Property grounds
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
9.2 out of 10, Wonderful, (37)
"We loved the brilliant use of space and all the amenities in this cozy hideaway. My husband, who owns a Professional Organization business, was very pleased and impressed by the clever use of various storage options. The walkways were attractively and effectively lit up for evening strolls and dog walking. All instructions were clearly communicated and our stay was lovely"
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Family House On Highland Lake with Dock
Fridge, microwave, oven, stovetop
Family House On Highland Lake with Dock
10.0 out of 10, Exceptional, (23)
"Stayed for labor day with family from out of state. Plenty of room for 4 adults and 4 kids, Could have easily fit more. Had a great time on the dock and having fires in the back yard. "
Family House On Highland Lake with Dock
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (205)
"My stay was shorter than I had planned but the few days I was here was so relaxing. First of all, the bed is so comfortable, I slept like a baby. Very quiet area. Nice to walk around with my dogs and explore. The cottage was nicely outfitted with any needs you might have. Beautiful time of year to stay here! I cannot wait to go back. I also want to say I appreciate that they allowed my two dogs. My dogs are very well behaved, and I travel with them quite often. Not all places allow this, so I...
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
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.