Photo by Kim Knox Beckius

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Compare 18 Cabin Rentals in Winsted with updated reviews, rates, and availability.

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (214)
"The cabin is quiet, tidy, and comfortable. It is within driving distance of several hiking trails and was a great place to spend a long weekend. The host was friendly and communicative, and made sure that we had everything we needed for a nice stay. "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Cozy & Chic Cabin by the Lake, with access to private Beach!

10.0 out of 10, Exceptional, (23)
"My partner and I stayed here for three days over the new year. Lovely location with very comfortable amenities. Perfect to just settle in and stay cozy in the winter. I will certainly be back during the warm weather to explore the nearby beach"
Cozy & Chic Cabin by the Lake, with access to private Beach!

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (40)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard

9.8 out of 10, Exceptional, (11)
"Great property. Exactly as advertised. "
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard

Berkshires Cabin 2 Mi to Appalachian Trail!

9.8 out of 10, Exceptional, (11)
"The cabin was pretty much all we could wish for to spend a few cozy days in the beautiful Berkshires! "
Berkshires Cabin 2 Mi to Appalachian Trail!

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

9.0 out of 10, Wonderful, (12)
"Enjoyed my stay . Went to fishing spots around the area. "
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Tolland Cabin w/ Private Hot Tub & Grill!

9.4 out of 10, Exceptional, (12)
"Cute cabin in a beautiful private setting. Very peaceful and surrounded by nature."
Tolland Cabin w/ Private Hot Tub & Grill!

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (6)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is SAR 1,894
SAR 3,243 total
includes taxes & fees
5 May - 6 May
Guesthouse Cabin vacation rentals in Berkshire County

Romantic and Secluded Berkshire's Gem

9.8 out of 10, Exceptional, (14)
"This was a perfect meet up spot for us and our friends from Westchester. It was cozy and clean and warm! A perfect spot to enjoy skiing at Butternut and to stay warm during and play in the snow during a snowstorm!"
Romantic and Secluded Berkshire's Gem

'The Mill River Cabin’ w/ Fireplace & River View!

9.8 out of 10, Exceptional, (38)
"We had a great time during our stay at the Mill Creek cabin! The views of the river couldn't be beat & we enjoyed spending time reading on the porch & watching the wildlife from the huge living room windows. We will definitely be back!"
'The Mill River Cabin’ w/ Fireplace & River View!

LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

9.6 out of 10, Exceptional, (5)
"Beautiful lake, traditional charming cottage- great get-away"
LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

East Otis Reservoir Cabin w/ Porch - Walk to Lake!

8.4 out of 10, Very Good, (8)
"Lovely cottage. Very clean. Everything we needed. We had a great time!"
East Otis Reservoir Cabin w/ Porch - Walk to Lake!

West Cornwall Cabin ~ 4 Mi to Covered Bridge!

9.4 out of 10, Exceptional, (6)
"Loved our stay!!!!"
West Cornwall Cabin ~ 4 Mi to Covered Bridge!

A-Frame Cabin w/ Furnished Deck in Becket!

8.4 out of 10, Very Good, (7)
"We had a wonderful stay in this adorable a frame!! Super cozy :)"
A-Frame Cabin w/ Furnished Deck in Becket!

Great Family Cabin in the woods on a lake.

10.0 out of 10, Exceptional, (2)
"The cabin and lake were even better than we expected. The cabin is fully equipped with almost everything you can think of for a comfortable stay. The lake water is very clean and the surrounding forest is sustainably maintained. Doolittle Lake is a hidden gem."
Great Family Cabin in the woods on a lake.

Serene Acreage - Pond - Hiking Trails Nearby

10.0 out of 10, Exceptional, (6)
"Wonderful accommodation."
Serene Acreage - Pond - Hiking Trails Nearby

Fantastic cottage in the Berkshire Mountains

10.0 out of 10, Exceptional, (1)
"This cabin is very well-maintained with all the amenities you could ask for... especially no cable TV, and the owner David is responsive and pleasant! It is the perfect place to unplug, unwind and reconnect with life, nature and whoever you're traveling with. The house is an easy 30 minutes to Tanglewood and 20 minutes to Great Barrington so there is plenty to see and do without feeling like always being in the car. We got takeout from a delicious Thai restaurant (Siam Square) in Great...
Fantastic cottage in the Berkshire Mountains

Cabin in the woods w cedar Hot Tub + private pond

Cabin in the woods w cedar Hot Tub + private pond
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

Family House On Highland Lake with Dock

10.0 out of 10, Exceptional, (24)
"Awesome location, plenty of space in the house, clean, and the host was very responsive. Will definitely stay here again when in Connecticut. "
Family House On Highland Lake with Dock

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

Lakefront Spring Stunner in New England Just 2 Hours From NYC

9.8 out of 10, Exceptional, (68)
"Overall a nice place to visit. A small family who likes the outdoors would enjoy it. "
Lakefront Spring Stunner in New England Just 2 Hours From NYC
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.