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Compare 19 Cabin Rentals in Winsted with updated reviews, rates, and availability.

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

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

10.0 out of 10, Exceptional, (17)
"great chic house, very clean"
Cozy & Chic Cabin by the Lake, with access to private Beach!
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
The Lake-we provide kayaks and a canoe!

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (209)
"The Cabin Had All The Amenities You Would Need and With A Quiet and Serene Area. For Me It Was Relaxing Stay!"
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Berkshires Cabin 2 Mi to Appalachian Trail!
Otis Vacation Rental | 3BR | 2BA | 1,200 Sq Ft | Stairs to Access

Berkshires Cabin 2 Mi to Appalachian Trail!

9.6 out of 10, Exceptional, (10)
"The hosts were extremely responsive and helpful, providing us with hiking ideas, questions regarding the house and suggesting best shopping spots for incidentals. The living room was cozy, seating five comfortably. The kitchen was well stocked so cooking a Thanksgiving meal was a pleasure. We thoroughly enjoyed ourselves."
Berkshires Cabin 2 Mi to Appalachian Trail!
'The Mill River Cabin’ w/ Fireplace & River View!
Mill River Vacation Rental | 2BR | 1BA | Stairs Required | 1,100 Sq Ft

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

9.8 out of 10, Exceptional, (37)
"The Mill River Cabin is the perfect location for a vacation focused on relaxation and communing with nature! We recently enjoyed a beautiful fall week at this property. Highlights included time spent on the deck overlooking the Konkapot River, evening campfires, hiking the large number/variety of trails very nearby, Hancock Shaker Village and the Norman Rockwell Museum. This rustic cabin has everything you need to make for an enjoyable stay. It's a good idea to bring your food and other...
'The Mill River Cabin’ w/ Fireplace & River View!
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required

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

9.8 out of 10, Exceptional, (38)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Serene Acreage - Pond - Hiking Trails Nearby

Serene Acreage - Pond - Hiking Trails Nearby

10.0 out of 10, Exceptional, (6)
"Wonderful accommodation."
Serene Acreage - Pond - Hiking Trails Nearby
Tolland Cabin w/ Private Hot Tub & Grill!
Tolland Vacation Rental | 2BR | 2BA | 1,200 Sq Ft | Stairs Required

Tolland Cabin w/ Private Hot Tub & Grill!

9.4 out of 10, Exceptional, (12)
"I want to preface my review by stating we had a wonderful time. We needed a getaway to unplug and relax and we were able to do just that. The area was beautiful, nature-plenty, quiet, secluded. There were a few unexpected glitches but nothing that we couldn't improvise around. Having said that, the listing said queen size beds, but they were only full, so my husband and I stayed in separate rooms which was sad . We also felt the people that prepped the home for our stay, must have ran short of...
Tolland Cabin w/ Private Hot Tub & Grill!
Romantic and Secluded Berkshire's Gem
Living area

Romantic and Secluded Berkshire's Gem

9.8 out of 10, Exceptional, (12)
"I recently had the pleasure of staying at a charming cabin in the woods, and it was an unforgettable experience! From the moment we arrived, we were greeted by the serene beauty of nature all around us. The cabin was cozy, beautifully decorated, and equipped with everything we needed for a comfortable stay. I highly recommend this cabin for anyone looking to escape the hustle and bustle of everyday life. It’s the perfect blend of comfort and adventure, and I can’t wait to return for another...
Romantic and Secluded Berkshire's Gem
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Spacious interior with tall ceilings and lots of light.

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

9.6 out of 10, Exceptional, (8)
"We had such a wonderful long weekend away that this home. Everything was exactly as pictured. Home was clean and so welcoming. Location was perfect for all that Great Barrington has to offer. The wraparound deck and fireplace made it all the more special. Communication was excellent and we got quick replies to any questions that came up. I would definitely recommend staying here and would happily return."
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK
Property grounds

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
A-Frame Cabin w/ Furnished Deck in Becket!
Becket Vacation Rental | 2BR | 1BA | 1,100 Sq Ft | Stairs Required to Enter

A-Frame Cabin w/ Furnished Deck in Becket!

8.4 out of 10, Very Good, (6)
"This A-frame cabin was the perfect location for some Berkshire R&R. Close to so many of western MA's greatest attractions, we had a great time visiting Tanglewood and museums, and touring local towns and restaurants. The property was clean, as described, and very comfortable. Communicating with our hosts was very simple. We will be happy to return!"
A-Frame Cabin w/ Furnished Deck in Becket!
Guesthouse Cabin vacation rentals in Berkshire County
Property grounds

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (5)
"Two very comfortable nights. Cabin is well appointed. Great kitchen and outdoor space. Tremendous views, amazing star gazing. Very private. "
The price is AED 1,928
AED 3,278 total
includes taxes & fees
1 Jan - 2 January 2025
Guesthouse Cabin vacation rentals in Berkshire County
East Otis Reservoir Cabin w/ Porch - Walk to Lake!
East Otis Vacation Rental | 2BR | 1BA | 720 Sq Ft | 2 Steps for Entry

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!
Great Family Cabin in the woods on a lake.
Pontoon dock with ladder and a float

Great Family Cabin in the woods on a lake.

10.0 out of 10, Exceptional, (2)
"We love this place as the lake is extremely quiet and clean. The house has a great living room with lots of charm and plenty of bathroom and bedroom space. I wish I had something bad to say because we could keep it to ourselves, but I do not."
Great Family Cabin in the woods on a lake.
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
West Cornwall Vacation Rental | 2BR | 2BA | Stairs Required | 1,521 Sq Ft

West Cornwall Cabin ~ 4 Mi to Covered Bridge!

10.0 out of 10, Exceptional, (5)
"This was a great, beautiful property to stay at. We are section hiking the AT and even went into NYC by train for a day. There were 6 of us and we were very comfortable. "
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
View of the cabin from the dock. The deck faces beautiful Lake Harwinton

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

9.0 out of 10, Wonderful, (12)
"We had a wonderful time at the cabin by the lake. Beautiful views in the Morning!! Loved it."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Fantastic cottage in the Berkshire Mountains
Our beautiful cabin

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
Half Moon by Avantstay 4BR Cabin w/ Large Deck & Yard w/ Patio & Outdoor Dining
Living area

Half Moon by Avantstay 4BR Cabin w/ Large Deck & Yard w/ Patio & Outdoor Dining

3.5 star property
Half Moon by Avantstay 4BR Cabin w/ Large Deck & Yard w/ Patio & Outdoor Dining
Cabin in the woods w cedar Hot Tub + private pond
Interior

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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Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Room

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
Front of home

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
Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (200)
"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"
Peace and quiet on the lake
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.