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Next weekend

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 103 Chalets in Windham with updated reviews, rates, and availability.

"Excellent location to skiing Spacious rooms Plenty of towels Kitchen stocked with appliances Close to market "

"The property was perfect for eight people. We stayed with our grown children and their plus ones. There was plenty of room for all of us to enjoy family time and quiet personal space , if needed. The kitchen was fully stocked and it was a nice location to skiing, Wilmington and local watering holes. The hot tub worked great and when the fire place was being finicky the property manager got right back to me to try and resolve the issue."

"Cabin was well thought out, super clean and a functional space. Close to Mt snow and Stratton. The only negatives was it is close to the road and driveway was muddy. We would definitely stay there again."

SAR 1,365 total

includes taxes & fees

20 May - 21 May

"The house was just what we needed for a family wedding in Manchester. Quite literally right off the highway but the house itself is nestled back and quiet so you don’t even hear the road. "

"Nice hill for sledding. Missed having electric mixer for potatoes. Nice community area of kitchen, dining room and living room. Good setup of rooms. "

SAR 3,260 total

includes taxes & fees

1 May - 2 May

"Stayed 3 nights everything was spotless & so very comfortable. This was our 2nd stay here. The host is always reachable & prompt to respond. Can’t wait to hopefully stay here again. "

"Fun family get away!"

"The house is in a great location for skiing at Stratton! 5 mins drive to the base or shuttle service running every 30 mins. Perfect for a cozy ski weekend with the fireplace. We enjoyed it very much! "

"We had 4 families with a range of kids from 16-5. The house was the perfect space to spread out to give everyone space and things to do! The house was clean and stocked with whatever you needed during the stay. We’ve done a lot of VRBO rentals and this was one of our best experiences! Plus, the trail was amazing to have in the backyard! "

"We had a great trip even though the weather did not cooperate. The home was just right for a group our size with plenty of extra room to spread out and relax. We loved the charm and feel of an old inn and close proximity to the mountain, town and shopping. Owners were very responsive and receptive to feedback. Would love to stay again. "

"This home was perfect for our stay. Spacious, clean, and comfortable, as well as kid-friendly with plenty of games and activities. The location is fantastic - super convenient for getting to restaurants and shops in town, and to Mt Snow. Would love to stay here again for our next visit!"

"We had a fabulous stay here. Owner was v communicative and accommodating."

"Helpful, fun and warm. "

SAR 2,535 total

includes taxes & fees

6 May - 7 May

"Great stay! We have a large family get together for the Thanksgiving weekend. Could not have been better. While not luxurious, It was clean and great for our stay! Hosts communication was spot on.and quick to respond to any questions. They provided all the necessities and were great! The area was convienent with much to do in downtown Wilmington."

"Our 2024 Christmas gift to our family was a ski weekend at Stratton Mountain. This property was perfect for us. Nestled in a wooded lot, it slept 10, kept us warm and cosy even in single digit temps. We would definitely recommend this property."

"Amazing! Host was readily available to handle any questions and the house was very comfortable and relaxing. "

"Clean, spacious house with modern finishes that was absolutely perfect for our trip with two families (four adults and five kids under 10). Extremely convenient to Okemo. Basement area was great for kids to hang out. Owner was highly responsive for random questions. We would definitely plan on staying here again. "

"Six of us women from Vermont golf courses stayed while playing a tournament at Haystack Country Club. The house suited us perfectly. We had some issues with the bathtub plumbing not turning off but we had prompt attention from a service person. The house had a great kitchen and tv to accommodate us."

SAR 1,289 total

includes taxes & fees

2 May - 3 May

"We had the best time at this cozy spot with some friends for a weekend - highly recommend!"

SAR 2,088 total

includes taxes & fees

5 May - 6 May

"The place was nice, the hosts were really excellent and responsive- and the location is very nice. It’s not too far to go hiking, swimming or kayaking!!!"

SAR 1,811 total

includes taxes & fees

22 May - 23 May

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Other property types in Windham

Smart TV, fireplace, foosball, table tennis

"This was the perfect house for a family and friend getaway. Spacious, clean with everything you need. The view from the hot tub was beautiful. The kids and grownups enjoyed sledding on the property."

"This place was absolutely perfect and wonderful. It offered a cozy family getaway to enjoy the southern Vermont scene that we have grown to love so very much. The house and owner are absolutely amazing and we hope to stay here again for our trips back to this area. Highly recommend! "

SAR 2,415 total

includes taxes & fees

1 May - 2 May