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Featured Chalets in Windham and around

HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin
9.6 out of 10, Exceptional, (39)
"The house has anything you want . A private house nice town . Quite,"
The price is €273
includes taxes & fees
7 Oct - 8 Oct
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin
Mountain Chalet with Breathtaking Panoramic Views
9.8 out of 10, Exceptional, (152)
"Check in process was smooth. Location was convenient for the event we attended. A few suggestions: washcloths should be provided, end of driveway needs to be regraded, no Food town discount card available as indicated, WiFi password should be more prominately displayed. Had a great time! "
Mountain Chalet with Breathtaking Panoramic Views
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
Rustic Mountain view Cabin 5 mins to Ski Area!
10.0 out of 10, Exceptional, (3)
"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!"
Rustic Mountain view Cabin 5 mins to Ski Area!
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
Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre
10.0 out of 10, Exceptional, (9)
"My sister and I rented the house for the weekend for our families - my family of five and her family of four. We have teenage kids. We stayed there for its proximity to the Full Moon Resort where our niece was getting married. The house was perfect for us. Plenty of space, so relaxing, super clean…and owner very responsive. Highly recommend. "
The price is €750
includes taxes & fees
2 Oct - 3 Oct
Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre
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
Beautiful Windham Chalet 2 minutes to Town and the Mountain
3.0 star property
Beautiful Windham Chalet 2 minutes to Town and the Mountain
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 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 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!
Catskill Chalet: Serene Mountain Escape
10.0 out of 10, Exceptional, (11)
"We wanted to spend a few days skiing at Belleayre and the house is conveniently located just a few minutes drive away. The premises were very clean and provided all of the comfort we needed during our staying. The pantry was nicely stocked and the kitchen had plenty of appliances to cook a storm if we wanted to. Room for improvement consists of better beds/mattresses (I know it is subjective but the twin bed is really too soft and the single ones weren't any better) and more tableware....
Catskill Chalet: Serene Mountain Escape
Never Lonesome Woodland Valley: Cozy 2bd Cottage!
9.8 out of 10, Exceptional, (8)
"I LOVE the rustic experience, as long as certain comforts are available. This cottage was the perfect balance, providing us the freshness of the creekside and all its wild greenery, some bugginess, and a clean place to rest that wasn’t overly sterile and bland. In fact, I found the furnishings to be very thoughtful, simple and pleasing; the kitchen and bathroom were well, but not overly, stocked; there was no clutter or worry that my small dog could get into anything he shouldn’t. This is easily...
Never Lonesome Woodland Valley: Cozy 2bd Cottage!
Secluded Chalet in the Northern Catskills with FIBER Internet and EV hookup
10.0 out of 10, Exceptional, (6)
"We like to meet up with some friends from Maine about once a year near the halfway point between us. Ray's Chalet is a great place to chill out and relax with friends and family. The Chalet is very clean and there's plenty of room for everybody. Great for grilling, lawn games, bonfires, etc. Ray adds a lot of nice touches as well, but I won't ruin the surprises for you. (BTW--Ray, thanks for the spare toothbrush set up! Saved our lives when we had to bring the kids at the last minute due to...
Secluded Chalet in the Northern Catskills with FIBER Internet and EV hookup
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 👀
Cozy Country Cabin with Amazing Mountain Farm Views and Nearby Lake! EV-King Bed
10.0 out of 10, Exceptional, (8)
"Relaxing remote location with lovely views of local farmland. Perfect wedding weekend getaway with our adult kids."
The price is €1,187
includes taxes & fees
2 Oct - 3 Oct
Cozy Country Cabin with Amazing Mountain Farm Views and Nearby Lake! EV-King Bed
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
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Other property types in Windham

Tuscan Year Round Beauty - Pickleball Court
10.0 out of 10, Exceptional, (94)
"Hard to decide where to begin…one of the nicest rental homes in the Windham area! Outside amenities are incredible - the firepit is amazing, the outdoor kitchen provides so many wonderful options (outdoor pizza oven was a hit) The inside provides fabulous space for all - even when the weather doesn’t cooperate. Rick and Alan were a pleasure to deal with. We look forward to a return trip!"
Tuscan Year Round Beauty - Pickleball Court
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
10.0 out of 10, Exceptional, (140)
"Great stay. Come here every year."
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
9.8 out of 10, Exceptional, (7)
"We could not have had a more comfotable stay! Bridget was quick to respond and ver helpful. The place easily fit our party of 13. We all had a restful weekend. Lots to do nearby but also no reason to want to leave this beatiful home. Highly reccomend!!!"
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
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.