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Compare 24 Chalets in East Windham with updated reviews, rates, and availability.

Beautiful Chalet, mins to Hunter/Windham slopes

10.0 out of 10, Exceptional, (10)
"Really lovely house with a beautiful view."
Beautiful Chalet, mins to Hunter/Windham slopes

Modern Rustic Log Chalet w/ mtn views, pool & bonus loft on 17 secluded acres

10.0 out of 10, Exceptional, (20)
"I booked the Hirox for a special restorative women’s wellness retreat centered around slowing down and immersing ourselves in the beautiful fall colors and mountain views. This place was absolutely perfect. Everything was clean, the kitchen so well stocked, and it was truly obvious how much thought and intention went into designing this lovely home. Joshua was so helpful in planning our weekend and was extremely responsive all the way through the booking process and our stay. I would absolutely...
Modern Rustic Log Chalet w/ mtn views, pool & bonus loft on 17 secluded acres

Chalet w/Covered HOT TUB & OUTDOOR TV; 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/Covered HOT TUB & OUTDOOR TV; fire pit, pool table, trail & playground!

COZY WINTER SKI Getaway w Fireplace & PRIVATE Indoor Pool! 5 mins to Hunter Mtn!

8.4 out of 10, Very Good, (54)
"Overall, nice private location. House was not as clean as it could have been . Owner responsive to messages and requests!"
COZY WINTER SKI Getaway w Fireplace & PRIVATE Indoor Pool! 5 mins to Hunter Mtn!

Beautiful Windham Chalet 2 minutes to Town and the Mountain

3.0 star property
Beautiful Windham Chalet 2 minutes to Town and the Mountain

Luxurious & Serene 2 Acre Mountain Cabin Retreat - 3 Bedrooms - Fully stocked

2.0 star property
10.0 out of 10, Exceptional, (1)
"We had such an amazing time at this house. It was extremely clean and had everything that we needed to have the perfect evening. The property is super nice and definitely took advantage of the gazebo overlooking the pond. The location is great and it is very close to both Hunter and Windham. We will definitely be coming back"
Luxurious & Serene 2 Acre Mountain Cabin Retreat - 3 Bedrooms - Fully stocked

Cozy Silo with Sunset Mountain Views

9.6 out of 10, Exceptional, (4)
"We had a nice time and would likely come again. Just two nitpicks: 1) the mattresses are extremely smushy and two people in our party had back issues. 2) the hot water runs out fast so one person had to take a cold shower. Overall, nice home in the woods. Thank you "
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

Private Chalet less than 1 mile to Ski Resort

9.6 out of 10, Exceptional, (5)
"Nice time away, owner was communicative and place served us well for what we needed"
Private Chalet less than 1 mile to Ski Resort

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

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, (8)
"Our family really enjoyed this home over a long fall weekend. The home is immaculate with plenty of space/bathrooms for my 3 adult kids and my husband and I. The kitchen is well stocked with everything needed. Plenty of paper products, soaps, basic spices. I appreciated how clean it was. Communication with the host was great, very responsive. We thoroughly enjoyed both the indoor fireplace and outdoor fire pit. Beautiful area for long hikes and to enjoy everything Windham has to offer. Would...
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, (3)
"We enjoyed our stay! Great views with the jacuzzi and fire pit. The house has all you need. Definitely will return just stay longer.. "
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! 🍁

Rustic Mountain view Cabin 5 mins to Ski Area!

10.0 out of 10, Exceptional, (4)
"I really enjoyed our stay at the chateau. Everything went smoothly and the place was well put together. There were a couple communication mishaps, but I think that was more related to the app than anything. Joseph was incredibly responsive and helpful throughout the whole weekend. I have definitely noted this place for a return visit in the winter!"
The price is AED 1,833
AED 2,094 total
includes taxes & fees
29 Jan - 30 Jan
Rustic Mountain view Cabin 5 mins to Ski Area!

Charming chalet with 5 bedrooms and WiFi, fitness room in peaceful Roxbury

2.0 star property
10.0 out of 10, Exceptional, (1)
"Nice living and dining space. Plenty of room to spread out. with 3 bedrooms up and 2 down you can. A few of the outlets are not currently working and there may be a yellowjacket nest that needs to be dealt with near the back deck. Outside of that I would rent it again "
Charming chalet with 5 bedrooms and WiFi, fitness room in peaceful Roxbury
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

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

10.0 out of 10, Exceptional, (146)
"We had another fun stay at the Dancing Horse Farm! The house has been upgraded with a new stove and other amenities. Huge home, to house several large families. Very well maintained and clean. We also visited the near by town for coffee and a nice brisk walk. Overall great time and look forward to coming again!"
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

8.2 out of 10, Very Good, (42)
"We had a great time at the cabin! It was the perfect escape from the city. The view was gorgeous, and the cabin had everything we needed. We also tried to use the canoe but the padlock is stuck, it might be rusted/need to be replaced. Otherwise everything was perfect!"
The price is AED 459
AED 533 total
includes taxes & fees
12 Jan - 13 Jan
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

The Cabin at Chichester in the Catskills Mountains

9.8 out of 10, Exceptional, (177)
"A beautiful, peaceful location to enjoy nature, yet be close enough to restaurants and shopping for convenience. We had four days of quiet and serenity in the warm, cozy, "feels like home" cottage. Our Labrador retriever loved exploring the woods and creekside (and barking at the wild turkeys!) Host Paul was attentive and gracious."
The Cabin at Chichester in the Catskills Mountains
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.