Search Chalets in Windham from CA $179

March 2025

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Browse Select Windham Chalets

1 Mile From Ski Slope and Festivals - 125 Nightly Fee

10.0 out of 10, Exceptional, (7)
"This studio is perfect for a weekend in Hunter. It is small, as advertised, but clean and functional and has all the necessities. The host was proactive in sending relevant information and highly responsive to my questions before and after we booked. The ski resort is a very short drive away. Downtown is lovely and Fellow cafe is not be be missed. "
The price is CA $179
CA $285 total
includes taxes & fees
Mar 30 - Mar 31
1 Mile From Ski Slope and Festivals - 125 Nightly Fee

Stunning Catskills Cabin Getaway, facing BelleAyre

9.8 out of 10, Exceptional, (123)
"Great property for a ski trip to Belleayre. Close to the mountain. "
Stunning Catskills Cabin Getaway, facing BelleAyre

Mountain Chalet with Breathtaking Panoramic Views

9.8 out of 10, Exceptional, (168)
"The house has an amazing view. The property was clean and very comfortable to stay in. Clear check in instructions and quick responses were provided by the host.We would definitely book this place again."
Mountain Chalet with Breathtaking Panoramic Views

Lakefront on the quiet side of main lake!

9.6 out of 10, Exceptional, (70)
"My family and I had a great time staying in Athens. The facilities allow for a host of activities such as getting out on the lake or going for a dip in a heated pool. The lake itself is much bigger than I had anticipated. The layout of the house works well and the basement was a great gathering spot especially on rainy days. The only sore spot was the garbage process. You’ll need to throw out trash using special bags provided by the HOA and we only received two bags. That’s not enough for a...
Lakefront on the quiet side of main lake!

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

10.0 out of 10, Exceptional, (20)
"Nice place for a skiing holiday"
Chalet w/Covered HOT TUB & OUTDOOR TV; fire pit, pool table, trail & playground!

Beautiful Windham Chalet 2 minutes to Town and the Mountain

3.0 star property
10.0 out of 10, Exceptional, (2)
"We planned a quick weekend getaway in the Catskills to ski and relax. This house was in the perfect location! "
Beautiful Windham Chalet 2 minutes to Town and the Mountain

Rustic Mountain view Cabin 5 mins to Ski Area!

10.0 out of 10, Exceptional, (4)
"Cozy great view close to the mountain"
Rustic Mountain view Cabin 5 mins to Ski Area!

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

9.6 out of 10, Exceptional, (46)
"Great location, Great Hot Tub, Great Catskills Mountains "
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

Beautiful Chalet, mins to Hunter/Windham slopes

9.8 out of 10, Exceptional, (15)
"Tons of room, well stocked kitchen, clean and tidy. Bunk beds were falling apart a bit- screws and pieces were loose- and the water in the house ran reddish brown every day until you ran the faucet for 15 min or so. Owner said it was from well water, which was fine, just not too appealing. We had a great trip overall and would likely rent 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, (14)
"The house was great for our ski trip to Bellayre Mountain. House was very well equipped with everything we needed for cooking and staying at house. Plenty of well appointed bedrooms and cozy wood stove."
The price is CA $642
CA $1,183 total
includes taxes & fees
Apr 2 - Apr 3
Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre

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

8.4 out of 10, Very good, (59)
"The home was nice and cozy. The owner was soo nice and soo responsive. Great place fo rent. "
COZY WINTER SKI Getaway w Fireplace & PRIVATE Indoor Pool! 5 mins to Hunter Mtn!

Cozy Silo with Sunset Mountain Views

9.8 out of 10, Exceptional, (7)
"Exactly as advertized. Cool architecture. Niece views."
Cozy Silo with Sunset Mountain Views

The Hunter Chalet

10.0 out of 10, Exceptional, (1)
"Would like to book for fall foliage trip."
The Hunter Chalet

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

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

10.0 out of 10, Exceptional, (22)
"This is our second time staying at the Hirox property. The house is beautiful, well stocked with everything you would need and more, and the surrounding mountains and forest is the ideal place to get away and relax. Two major ski resorts within 30 min distance makes this the absolute perfect place to stay. The hosts are the most conscientious, responsive and caring people that I have ever encountered in my entire history of renting. We had snow storms, wind storms and tons of questions and not...
Modern Rustic Log Chalet w/ mtn views, pool & bonus loft on 17 secluded acres

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

2.0 star property
8.0 out of 10, Very good, (4)
"We were a group of two families and the bedrooms upstairs and on the lower level allowed each family some privacy with lots of shared space on the main floor. The location was awesome, felt remote but was about 5mins into town and close to Plattekill Mt for skiing. There were a few missing essentials for cooking like serving and mixing bowls but the espresso machine was top notch. "
Charming chalet with 5 bedrooms and WiFi, fitness room in peaceful Roxbury

Modern Swiss Ski Chalet with Tennis Court, Outdoor pit and multiple fireplaces

10.0 out of 10, Exceptional, (2)
"Great location and decent building! Amina is such a nice host and a huge plus! She was accommodating and answered all our requests and questions promptly and solved issues in a timely manner. The only thing we would like to remind the other guest is that please bring lots and lots of bottled water since the tap water is slimy and you need bottle water for both cooking and drinking."
Modern Swiss Ski Chalet with Tennis Court, Outdoor pit and multiple fireplaces

Luxury 3300 sqft Ski & Golf Chalet,2 fireplaces & Firepit.5 min from Windham Ski

10.0 out of 10, Exceptional, (2)
"We love the cabin and the location is even better. Plenty of room for two families and the property is very well kept. We would definitely stay again. Thanks!"
The price is CA $715
CA $1,412 total
includes taxes & fees
Mar 30 - Mar 31
Luxury 3300 sqft Ski & Golf Chalet,2 fireplaces & Firepit.5 min from Windham Ski

Luxe Party Retreat: Theater/Karaoke/Games/Hot tub/swimming pool

10.0 out of 10, Exceptional, (1)
"Everything was as advertised and do easy to use. It was luxurious and modern yet cozy and accessible. Steve was a delight and so helpful as a host. We will absolutely be back."
Luxe Party Retreat: Theater/Karaoke/Games/Hot tub/swimming pool

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
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 Windham

A'Neils Windham Ski Lodge & Family Retreat

10.0 out of 10, Exceptional, (28)
"A wonderful space for a family reunion ski get away. Enough personal space for each while also offering great shared space for warm gatherings and meals. Host was very accommodating and easily available. We would definitely stay again!"
A'Neils Windham Ski Lodge & Family Retreat

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

10.0 out of 10, Exceptional, (154)
"Large home with everything you’ll need. Plenty of towels, kitchen supplies, fridge space for a large party. Bedding was nice, with plenty of extra blankets. Greg was very easy to work with and answered all of our questions quickly. We would definitely book this property 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, (98)
"Awesome"
Tuscan Year Round Beauty - Pickleball Court
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.