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Compare 27 Chalets in East Windham with updated reviews, rates, and availability.

Beautiful Chalet, mins to Hunter/Windham slopes
10.0 out of 10, Exceptional, (7)
"We booked our house for a mini family reunion and this house was perfect. The house was clean and well stocked, the beds were very comfortable and the setting of the house was calming and peaceful. We would definitely book again"
Beautiful Chalet, mins to Hunter/Windham slopes
Charming chalet with 5 bedrooms and WiFi, fitness room in peaceful Roxbury
2.0 star property
Charming chalet with 5 bedrooms and WiFi, fitness room in peaceful Roxbury
Charming Log Chalet w/ huge deck, pool & bonus garage loft on 17 secluded acres
10.0 out of 10, Exceptional, (19)
"We had a great time! The house and view of the mountains was beautiful and was exactly what we expected. Joshua was a great host and responded quickly to questions. Highly recommend!"
Charming Log Chalet w/ huge deck, pool & bonus garage loft on 17 secluded acres
Chalet w/ OUTDOOR TV & HOT TUB; POOL, fire pit, pool table, trail & playground!
10.0 out of 10, Exceptional, (17)
"Great location, lots of local hiking, beautiful area. House had a ton to offer for the kids, but we spent most of the time outside! Hosts very quick to respond and included thoughtful extras for our dogs. Highly recommend!"
Chalet w/ OUTDOOR TV & HOT TUB; POOL, fire pit, pool table, trail & playground!
BEAUTIFULLY SECLUDED- Spring, Summer Getaway w PRIVATE Indoor Pool
8.4 out of 10, Very Good, (51)
"Overall, nice private location. House was not as clean as it could have been . Owner responsive to messages and requests!"
BEAUTIFULLY SECLUDED- Spring, Summer Getaway w PRIVATE Indoor Pool
Cozy Silo with Sunset Mountain Views
10.0 out of 10, Exceptional, (3)
"Absolutely loved the place and location. Unique building, being a silo, but the layout is fantastic. Great main floor with deck, wonderful private master upstairs with well done bathroom. We did not use the downstairs for sleeping, bottom floor ( tri level) but walked through and seems just as well done as the rest. Loved sitting on the deck at night with the fire pit going, just chilly enough to enjoy it a keep the bugs away ( weren’t bad anyway). Our headquarters for hiking and exploring....
Cozy Silo with Sunset Mountain Views
Lakefront w/Dock! Family Friendly Amenities, Close to skiing and Hudson, NY
8.8 out of 10, Excellent, (6)
"We very much enjoyed our time spent at Eagles Nest playing pickleball, ping pong, time at the pool and using the various boating equipment. Just beware as you may encounter a water snake or 2 but they are timid and we continued enjoying the dock activities such as fishing, kayaking, paddleboating or just laying on the floating mat. The kitchen and laundry room were extremely well appointed as was each bedroom with it's own tv. The lake is also an extremely quiet body of water. The one slight...
Lakefront w/Dock! Family Friendly Amenities, Close to skiing and Hudson, NY
🏔Windham🏔 - Hot Tub🛀Game Room🕹Fire Pit🔥Ski Views 👀
10.0 out of 10, Exceptional, (21)
"We had a great weekend at the Manor. The game room was excellent and provided entertainment for everyone."
🏔Windham🏔 - Hot Tub🛀Game Room🕹Fire Pit🔥Ski Views 👀
Modern Swiss Ski Chalet with Tennis Court, Outdoor pit and multiple fireplaces
Modern Swiss Ski Chalet with Tennis Court, Outdoor pit and multiple fireplaces
Never Lonesome Hunter: Smart 4bd Getaway near Mtn
10.0 out of 10, Exceptional, (2)
"Nice little house to stay in if you're looking to spend time in the mountains. It's old, for sure, but it was comfortable and conveniently located. Hosts were great about communicating. It was a nice, chill vacation."
Never Lonesome Hunter: Smart 4bd Getaway near Mtn
Windham Immaculate Ski Chalet with Awesome Fire Pit.
9.8 out of 10, Exceptional, (7)
"We are a big family with 4 kids between 6 and 17 year old. The house is the perfect size for us! It's very clean and the linens are very comfortable. The location is so convenient! Less than 10 min drive to Windham ski resort. Peter is very responsive and accommodating! We had a great time!"
Windham Immaculate Ski Chalet with Awesome Fire Pit.
Chalet near Windham w/ hot tub
Chalet near Windham w/ hot tub
5 Star Gorgeous Cliffside Chalet with Panoramic Views
10.0 out of 10, Exceptional, (1)
"This home is a beautiful refuge. Lots of windows offer breathtaking views and colorful sunsets. The house is well-furnished and equipped. The owner was accessible and invested in our comfort in his home. Renters should understand, however, that the primary bedroom is in a loft, with no shades or drapes to cover the windows. If all that light/exposure would be a sleep issue for other renters, they should bring a good sleep mask. "
5 Star Gorgeous Cliffside Chalet with Panoramic Views
Cabin w/ Mountain Views, Hot Tub, AC, Pet + Family Friendly, WFH, Fireplace
10.0 out of 10, Exceptional, (2)
"We had a great time staying at this house for the weekend. Everything was awesome and so thoughtfully put together. The attention to details made our experience even more special. The hot tub with the view and car charger were welcome amentities. I highly recommend this place!"
Cabin w/ Mountain Views, Hot Tub, AC, Pet + Family Friendly, WFH, Fireplace
🍂 Fall Escape! Stunning 3BR/3BA Condo on Hunter Mountain - Book Now! 🍁
🍂 Fall Escape! Stunning 3BR/3BA Condo on Hunter Mountain - Book Now! 🍁
Luxurious 3BR/2BA Chalet w/ Panoramic Views Near Windham Mountain on 22+ Acres
Luxurious 3BR/2BA Chalet w/ Panoramic Views Near Windham Mountain on 22+ Acres
Mountain-Top Getaway with Hot Tub and Game Room!
Mountain-Top Getaway with Hot Tub and Game Room!
Charming Catskill Chalet near Belleayre
Charming Catskill Chalet near Belleayre
Stunning A Frame Chalet, Game Rm, 5 min Windham Mt
Stunning A Frame Chalet, Game Rm, 5 min Windham Mt
Beautiful Windham Chalet 2 minutes to Town and the Mountain
3.0 star property
Beautiful Windham Chalet 2 minutes to Town and the Mountain
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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 East Windham

Tuscan Year Round Beauty - Pickleball Court
10.0 out of 10, Exceptional, (94)
"Rick was an amazing host and the property exceeded expectations and the views are amazing. Well worth it. "
Tuscan Year Round Beauty - Pickleball Court
Romantic sky loft with steam shower/giant tub. Minutes to the slopes.
10.0 out of 10, Exceptional, (13)
"We really enjoyed our stay at the loft! We went to see a show at the Bearsville Theater in Woodstock and this place was under 20 mins from the venue. Very comfortable king size bed, loved the rustic boho vibes. The bathroom was a dream, highly recommend indulging in the steam shower and doing a cold tub plunge afterwards! Overall this was a beautiful spot tucked in the mountains and we can’t wait to come back and check out the town that’s just a short walk down the road."
Romantic sky loft with steam shower/giant tub. Minutes to the slopes.
THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE
10.0 out of 10, Exceptional, (85)
"Each year we go on vacation with our daughter, son in law and his family. We are a group of 12 and loved this lake house. We all want to make this our yearly trip. Great place"
The price is SAR 1,501
SAR 2,661 total
includes taxes & fees
14 Oct - 15 Oct
THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE
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.