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Compare 21 Cabin Rentals in Windsor with updated reviews, rates, and availability.

"The Cabin Had All The Amenities You Would Need and With A Quiet and Serene Area. For Me It Was Relaxing Stay!"

Otis Vacation Rental | 3BR | 2BA | 1,200 Sq Ft | Stairs to Access

"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."

"It was beautiful to wake up the first morning to see freshly fallen snow! Easy to get to, lots for the kids to do, wonderful place to share with my family for Thanksgiving! Only thing that I would change is having wood in the wood holder by the stove so that we didn’t have to carry it in. Would recommend to others. "

AED 2,191 total

includes taxes & fees

29 Dec - 30 Dec

"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,...

"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!"

"Great"

"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...

Becket Vacation Rental | 2BR | 1BA | 1,100 Sq Ft | Stairs Required to Enter

"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!"

Cozy log cabin nestled among snow covered trees. The perfect winter wonderland!

"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."

Goshen Vacation Rental | 2BR | 1BA | 725 Sq Ft | Stairs Required for Access

"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...

Westhampton Vacation Rental | 3BR | 1.5BA | Stairs Required | 1,705 Sq Ft

"Loved our stay. "

"Great location, comfortable, beautiful setting and nice porch! "

"A wonderful cabin with all the amenities you will need. Clean, beautifully decorated, and so much room. Highly recommend! Will be back for sure. "

"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. "

Stockbridge Vacation Rental | 2BR | 2BA | 700 Sq Ft | Stairs Required

"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 and charming. Overall great experience. Would recommend"

"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. "

A floor-to-ceiling fieldstone fireplace highlights the living space.

"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."

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Other property types in Windsor

"Nice and quiet family get a way"

AED 792 total

includes taxes & fees

1 Jan - 2 January 2025

"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....

AED 754 total

includes taxes & fees

1 Jan - 2 January 2025

"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!"