Search Chalets in Windham from CA $201

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Browse Select Windham Chalets

Mountain Chalet with Breathtaking Panoramic Views

9.8 out of 10, Exceptional, (161)
"The property location was beautiful and all prior reviews were spot on. The views were all that and more. Waking up to the sunrise peeking over the mountains was majestic and peaceful. We were incredibly lucky to experience a snowstorm and woke up to 6” on Thxgiving morning. It was just perfect. We had a fire and made a snowman. My dog had a great time in the snow. We all cooked an amazing Thxgiving dinner together in the well equipped kitchen that even had a turkey baster (impressed). ...
Mountain Chalet with Breathtaking Panoramic Views

HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

9.6 out of 10, Exceptional, (40)
"The house has anything you want . A private house nice town . Quite,"
The price is CA $201
CA $367 total
includes taxes & fees
Jan 8 - Jan 9
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre

10.0 out of 10, Exceptional, (11)
"Absolutely perfect weekend getaway. The house offered plenty of space for our group of 10. The fireplace made it so cozy. With the current outdoor burn ban, we didn't get to enjoy the firepit but the property was beautiful and scenic. The host was very easy to communicate with and very responsive. Definitely recommend!waybto c"
The price is CA $649
CA $1,195 total
includes taxes & fees
Jan 7 - Jan 8
Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre

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

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!

9.4 out of 10, Exceptional, (9)
"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

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 👀

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 CA $576
CA $1,480 total
includes taxes & fees
Jan 7 - Jan 8
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

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
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.
Don't see what you're looking for?
See all available properties in Windham
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Windham

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

10.0 out of 10, Exceptional, (145)
"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

Tuscan Year Round Beauty - Pickleball Court

10.0 out of 10, Exceptional, (97)
"Awesome"
Tuscan Year Round Beauty - Pickleball Court

GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.

9.8 out of 10, Exceptional, (9)
"We loved this house. We had 25 people (ages 5 through 84) for Thanksgiving and thoroughly enjoyed our stay from Tuesday through Sunday. Bridget is very quick to answer our emails."
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.