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Compare 23 Cabin Rentals in Windsor with updated reviews, rates, and availability.

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, (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
Bear Creek Cabin
Exterior
Bear Creek Cabin
10.0 out of 10, Exceptional, (18)
"Great cabin, modern, clean, and comfortable."
The price is AED 1,469
AED 2,211 total
includes taxes & fees
24 Sep - 25 Sep
Bear Creek Cabin
Vermont Lake Front Log Cabin Close to Mt. Snow
View from the lake
Vermont Lake Front Log Cabin Close to Mt. Snow
10.0 out of 10, Exceptional, (61)
"From the very beginning everything went smoothly. Cabin is exceptional and being right on the lake is even better. We had an amazing time tucked away here."
Vermont Lake Front Log Cabin Close to Mt. Snow
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!
9.8 out of 10, Exceptional, (8)
"This is my second summer renting this house. It's great. Beautiful home, lots of light, in the woods, very comfortable. Our first year we had a rainy Sunday and it was fun to just hang out in. Very clean. The rental contact person was very responsive to a question we had. Five minutes from Jacob's Pillow. Lenox/Lee/Stockbridge are all just a quick drive away. Very quiet rural setting. A deer visited us this year, early on Sunday morning. Love this place."
Berkshires Cabin 2 Mi to Appalachian Trail!
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
10.0 out of 10, Exceptional, (22)
"Three of us had a great stay! The cottage was very clean and very well outfitted. It was clear that the hosts put a lot of thought into making sure guests would have everything they need. The space is bright and modern but still cozy, very nicely designed. The lake was a bit more of a walk than I had imagined it would be and there isn’t much of a sitting area by the lakefront but the lake itself is beautiful. Overall, a very nice cottage and lovely stay!"
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Exterior
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
9.6 out of 10, Exceptional, (59)
"Great"
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Lakefront House with Stunning Views and Great Room
Property grounds
Lakefront House with Stunning Views and Great Room
9.8 out of 10, Exceptional, (14)
"The house was nice and worked for our family. We were able to fish, kayak and swim. There was plenty of outdoor space to play games and spread out. There were plenty of outdoor chairs to use and beach towels as well. The kitchen was very well appointed with dishes and all the utensils that we needed. I was disappointed with the cleanliness. The kitchen sink was ceramic and was very stained and dirty. I cleaned it and it came out very well. The other item that should have been looked at before...
Lakefront House with Stunning Views and Great Room
A-Frame Cabin in Becket: Deck + Private Acreage!
Becket Vacation Rental | 2BR | 1BA | Stairs Required | 1,100 Sq Ft
A-Frame Cabin in Becket: Deck + Private Acreage!
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 in Becket: Deck + Private Acreage!
Berkshires Log Cabin by Evergreen Home
Charming Log Cabin with wrap around porch!
Berkshires Log Cabin by Evergreen Home
10.0 out of 10, Exceptional, (7)
"We pulled in to a lighted log cabin that was lit by lights around the porch. You feel as if you are alone in the middle of the woods. It seemed all the restaurants were 20 minutes away. No shortage of good restaurants. We went to Tanglewood twice and what a treat. We saw Kool and the Gang and John Baptiste. Great performers playing in the Berkshires."
Berkshires Log Cabin by Evergreen Home
Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Goshen Vacation Rental | 2BR | 1BA | 725 Sq Ft | Stairs Required for Access
Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!
9.0 out of 10, Wonderful, (28)
"This is a rustic, perfectly well outfitted cabin. Had everything that we needed in the kitchen. The beds and the couches were very comfortable. Bonus points for the well water being really soft and tasting good. It’s a sweet little spot. So grateful it is pet friendly!"
Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Lakefront Westhampton Cabin w/ Beach + Kayaks!
Westhampton Vacation Rental | 3BR | 1.5BA | Stairs Required | 1,705 Sq Ft
Lakefront Westhampton Cabin w/ Beach + Kayaks!
10.0 out of 10, Exceptional, (5)
"Our two weeks on the lake were filled with swimming, kayaking, hammock napping and eating. My daughter and I hosted guests and day trippers, almost filling the bunkhouse! The house itself is pristine, tastefully appointed and well stocked, from towels to firewood. A welcome basket from a local bakery awaited us. Our dogs were happy, too! The lake is perfect - the only sounds you can hear are happy kayakers and rowers talking to each other, and the mallard ducks quacking. A very serene and lovely...
Lakefront Westhampton Cabin w/ Beach + Kayaks!
Artist's Camp on Lake Mahkeenac
Interior
Artist's Camp on Lake Mahkeenac
9.8 out of 10, Exceptional, (17)
"Great location, comfortable, beautiful setting and nice porch! "
Artist's Camp on Lake Mahkeenac
Modern Cabin Near Tanglewood
Living area
Modern Cabin Near Tanglewood
10.0 out of 10, Exceptional, (8)
"A wonderful cabin with all the amenities you will need. Clean, beautifully decorated, and so much room. Highly recommend! Will be back for sure. "
Modern Cabin Near Tanglewood
Lakeshore cabin with private beach and dock
Exterior
Lakeshore cabin with private beach and dock
10.0 out of 10, Exceptional, (2)
"Took advantage of the peaceful setting and location to nearby attractions!"
Lakeshore cabin with private beach and dock
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Stockbridge Vacation Rental | 2BR | 2BA | 700 Sq Ft | Stairs Required
Cozy Stockbridge Cabin - Walk to Beach & Lake!
9.4 out of 10, Exceptional, (8)
"If you’re going to events at Tanglewood, this is a prime location. We added on an extra concert because of the easy 6 minute drive. This little lake cabin was quaint and cozy. The outdoor shower was superb. Would definitely stay here again! "
Cozy Stockbridge Cabin - Walk to Beach & Lake!
The Pocumtuck Cabin @ The Wigwam Western Summit
Property grounds
The Pocumtuck Cabin @ The Wigwam Western Summit
10.0 out of 10, Exceptional, (1)
"My boyfriend and I stayed one night. The cabins were cozy and had a great view of the mountains. Lea is a wonderful host and provided us with complimentary coffee and tea. I would definitely go back again!"
The Pocumtuck Cabin @ The Wigwam Western Summit
Mahican Cabin - A Private Nature's Reserve For 2
Property grounds
Mahican Cabin - A Private Nature's Reserve For 2
10.0 out of 10, Exceptional, (2)
"Great customer service by hosts and adorable spot with an incredible view for a night or two away."
Mahican Cabin - A Private Nature's Reserve For 2
Charming A-Frame Near all the Best parts of the Berkshires!
Exterior
Charming A-Frame Near all the Best parts of the Berkshires!
10.0 out of 10, Exceptional, (1)
Charming A-Frame Near all the Best parts of the Berkshires!
Den Outdoors Cabin With STUNNING Adirondack Views - EV charging available
Exterior
Den Outdoors Cabin With STUNNING Adirondack Views - EV charging available
2.0 star property
10.0 out of 10, Exceptional, (1)
"Wow - from the great looking property, the well appointed amenities, and a sunset that will keep you captivated, we had a lovely experience! The house had everything for a convenient and comfortable stay, along with a lot of character that made every day special. Great communication with the host helped us feel at home. The thoughtful preparation of a ready fire in the hot tub was a nice touch! Thanks, Matthew, for a great stay. "
Den Outdoors Cabin With STUNNING Adirondack Views - EV charging available
Shelburne Studio Cabin w/ Spring-Fed Pool!
A floor-to-ceiling fieldstone fireplace highlights the living space.
Shelburne Studio Cabin w/ Spring-Fed Pool!
8.4 out of 10, Very Good, (12)
"Perfect little cabin in the woods. You feel a million miles away from the hustle and bustle of a busy town yet you’re right around to corner to a lot of conveniences. Love it."
Shelburne Studio Cabin w/ Spring-Fed Pool!
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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 Windsor

Vacation Village in the Berkshires
Lobby
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1714)
"Nice place. Pleasantly surprised how big the suite was. The whole place was very clean from the suite itself, the huge indoor pool and hot tub. The clerk that checked us in was very knowledgeable of the area and just a pleasant person. She is an older lady, I forget her name but she is a definite asset to this property! On the down side the path to the main office was not well lit but we used our flashlights. Also there isn't restaurants on site or groceries available. We had to travel 25...
The price is AED 620
AED 717 total
includes taxes & fees
24 Sep - 25 Sep
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Property entrance
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (897)
"Was good everything "
The price is AED 537
AED 589 total
includes taxes & fees
26 Sep - 27 Sep
Jiminy Peak Mountain Resort
Pristine Home In Becket Woods
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (9)
"Near Jacob's Pillow!"
Pristine Home In Becket Woods
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.