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Compare 20 Cabin Rentals in Windsor with updated reviews, rates, and availability.

Bear Creek Cabin

9.8 out of 10, Exceptional, (20)
"The home was beautiful and we enjoyed our stay! The only thing about the location, it’s very remote. We had an event in North Adams and had a nearly impossible time getting a ride share service or taxi to come pick us up. Other than that, a wonderful stay!"
The price is AED 1,469
AED 2,220 total
includes taxes & fees
2 Dec - 3 Dec
Bear Creek Cabin

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!

9.8 out of 10, Exceptional, (9)
"Enjoyed the foliage and some nice hikes. House was comfortable and clean. Owner was responsive and helpful. We arrived at night and had trouble locating the property when our gps failed. Owner was helpful guiding us to the house. I suggest arriving in the light of day. "
Berkshires Cabin 2 Mi to Appalachian Trail!

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!

Vermont Lake Front Log Cabin Close to Mt. Snow

10.0 out of 10, Exceptional, (64)
"I can’t say enough about our host, Bob, and this property. If you’re looking for a peaceful slice of heaven, this immaculate log cabin is the place. This is the cleanest rental we’ve ever stayed in and the attention to detail was incredible. The kitchen was super stocked and the furniture was comfortable, we immediately felt at home. The Firepit by the water was so relaxing and the fireplace inside was great to end the day. Thanks to Bob for the wood. Bob was extremely responsive and friendly,...
Vermont Lake Front Log Cabin Close to Mt. Snow

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

10.0 out of 10, Exceptional, (23)
"My partner and I really enjoyed our relaxing stay at this quaint cottage. It was clean, comfortable, and tucked away in a very quiet area. It was easy to get to restaurants and theaters in Pittsfield / Lenox / Stockbridge. The hot tub was also a great way to spend a cozy fall afternoon!"
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

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

9.6 out of 10, Exceptional, (15)
"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

Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!

9.0 out of 10, Wonderful, (30)
"This Pet-Friendly Cabin was very cozy. It is in a woodland neighbor of cabins, but it feels very secluded. Nobody was at the one cabin that we could see. The weather was cool while we were there, so we enjoyed a campfire outside and one in the indoor fireplace. The cabin was decorated by someone like my grandma who was obsessed with bears and apples. The cabin is a short stroll from a lake with a beach. Although our overall experience was good, there are few negatives. First, there are no...
Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!

Lakefront Westhampton Cabin w/ Beach + Kayaks!

10.0 out of 10, Exceptional, (6)
"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

9.6 out of 10, Exceptional, (18)
"Great location, comfortable, beautiful setting and nice porch! "
Artist's Camp on Lake Mahkeenac

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

10.0 out of 10, Exceptional, (3)
"We love this place! It is conveniently located for Tanglewood and the Rockwell museum, quiet and secluded. The cabin and grounds show much care and attention by thoughtful owners. "
Lakeshore cabin with private beach and dock

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!

Charming A-Frame Near all the Best parts of the Berkshires!

10.0 out of 10, Exceptional, (2)
"Cozy and charming. Overall great experience. Would recommend"
Charming A-Frame Near all the Best parts of the Berkshires!

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!

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!

Dadzpad Cabin in Stephentown

Dadzpad Cabin in Stephentown

Into the Woods- Berkshire Cabin Retreat!

2.0 star property
Into the Woods- Berkshire Cabin Retreat!

Cool Converted Cabin with strong wifi in Whitingham

Cool Converted Cabin with strong wifi in Whitingham
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

3.0 star property
8.6 out of 10, Excellent, (1746)
"Property was beautiful, great staff "
The price is AED 620
AED 717 total
includes taxes & fees
1 Dec - 2 Dec
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is AED 657
AED 721 total
includes taxes & fees
28 Nov - 29 Nov
Jiminy Peak Mountain Resort

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
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.