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9 Jum. I - 11 Jum. I

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16 Jum. I - 18 Jum. I

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30 Jum. I - 1 Jum. II

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27 Jum. II - 29 Jum. II

Compare 27 Cabin Rentals in Windsor with updated reviews, rates, and availability.

"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. "

"Loved it, will definitely book again!"

SAR 2,208 total

includes taxes & fees

12 May - 13 May

"Great place to stay with friends and family. Will be visiting again!"

SAR 1,207 total

includes taxes & fees

4 May - 5 May

"We had a great time in the cottage. It was perfectly cozy for our family of 6. The cottage has everything you need to have fun on a cold winter night. We especially enjoyed the hot tub and board games! Thanks for a lovely stay - we will come back in the summer!"

"The cabin was pretty much all we could wish for to spend a few cozy days in the beautiful Berkshires! "

"What an incredible property, town and area. If you’re looking to get away for a bit in New England, it’d be hard to beat this place. Absolutely loved it, close to many small towns with great food and shops and views. Will be back again!!"

"We had an amazing time at the house and lots of fun on the lake. This was a cozy home with family history and thoughtful touches. A great stay."

SAR 2,446 total

includes taxes & fees

3 May - 4 May

2 bedrooms, iron/ironing board, internet, bed sheets

"Charming decor and solid furniture. Lovely screened porch and deck. Micro kitchen—smaller that we expected but we’ll-equipped. Bedrooms also smaller than expected. Beds were good. "

"We had a wonderful stay in this adorable a frame!! Super cozy :)"

"Over all we loved this cabin. The outdoor spaces are wonderful. Dusk setting over the lake while sitting on deck with a drink was as close to perfection as you can get. We enjoyed kayaking around the lake. Very peaceful. The cabin is large. We used the fireplace every night. The only knock is the bugs and cobwebs in the high spaces. "

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

"House was clean and comfortably furnished. The kids enjoyed the arcade games and it was an overall good time. Only Issues were that the drive and walk ways were hidden in the snow and the house did not hold heat well "

"We had a great time staying in Lauren and Blake's cabin. It was very comfortable, clean and convenient and I would definitely stay there again. Thank you for being great hosts!"

"Loved our stay. "

"This cabin was just perfect for our family vacation to the Berkshires. It was clean, had everything we needed, and Marlena was extremely helpful and responsive. We hope to be back some day!"

"Took advantage of the peaceful setting and location to nearby attractions!"

"Location of this property is near all things Stockbridge has to offer. Easy ride to Tanglewood Short ride to Lenox and Lee The cottage is an older gem Well stocked and lots of quirky charm"

"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. "