Search Chalets in Windham from CA $636

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Browse Select Windham Chalets

Mountain Chalet with Breathtaking Panoramic Views

9.8 out of 10, Exceptional, (165)
"Very pleasant stay close to markets, restaurant and ski resort. Lee was very responsive "
Mountain Chalet with Breathtaking Panoramic Views

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

10.0 out of 10, Exceptional, (12)
"Everything was wonderful."
The price is CA $636
CA $1,172 total
includes taxes & fees
Feb 23 - Feb 24
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, (12)
"Easy trip to the mountain. Beautiful view. Plenty of room. "
Beautiful Chalet, mins to Hunter/Windham slopes

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

8.4 out of 10, Very good, (56)
"Perfect for our ski/snowboarding getaway! Very secluded location. "
COZY WINTER SKI Getaway w Fireplace & PRIVATE Indoor Pool! 5 mins to Hunter Mtn!

This spacious log cabin on a back mountain road leads directly to Hunter ski lifts

This spacious log cabin on a back mountain road leads directly to Hunter ski lifts

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 $842
CA $1,552 total
includes taxes & fees
Mar 10 - Mar 11
Luxury 3300 sqft Ski & Golf Chalet,2 fireplaces & Firepit.5 min from Windham Ski

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

Beautiful Windham Chalet 2 minutes to Town and the Mountain

3.0 star property
10.0 out of 10, Exceptional, (1)
"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, (42)
"Everything was easy. It would be nice to have hand towels, washcloths, and paper towels. The heat is a bit tricky but once you figure it out everything is good to go. "
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

Cozy Silo with Sunset Mountain Views

9.6 out of 10, Exceptional, (5)
"We wanted to get out of the city for a few days and this was the perfect spot. It was so cozy, clean, and we got lucky to get snow! Olga was super communicative and a great host. "
Cozy Silo with Sunset Mountain Views

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

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

10.0 out of 10, Exceptional, (19)
"We stayed for Christmas to be close to family ! Very cozy yet spacious ! Kids loved the pool table and hot tub . "
Chalet w/Covered HOT TUB & OUTDOOR TV; fire pit, pool table, trail & playground!

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

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

2.0 star property
8.0 out of 10, Very good, (2)
"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

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

10.0 out of 10, Exceptional, (21)
"Amazing property with excellent hosts.Our whole family loved!!!"
Modern Rustic Log Chalet w/ mtn views, pool & bonus loft on 17 secluded acres

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."
Cozy Country Cabin with Amazing Mountain Farm Views and Nearby Lake! EV-King Bed

Private Chalet less than 1 mile to Ski Resort

9.8 out of 10, Exceptional, (6)
"I stayed here with my husband and our daughter (almost 3) for a weekend ski trip to Hunter Mountain. It was the perfect little spot for our family (and more!), it was cozy and clean and right near the mountain. We could not have asked for more. "
Private Chalet less than 1 mile to Ski Resort

Cozy & Modern Catskills Cabin on 4 Acres with Wood Fired Hot Tub and Firepit

10.0 out of 10, Exceptional, (1)
"Clean, calming, everything functioning, nice new woodwork and good kitchen set up. AC is effective, superb lightening choices.. Great location, access to many places, in a quiet neighborhood. Would return here. infoor and outdoor."
Cozy & Modern Catskills Cabin on 4 Acres with Wood Fired Hot Tub and Firepit
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

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

9.2 out of 10, Wonderful, (39)
"Easy and convenient, would stay again. "
The price is CA $241
CA $357 total
includes taxes & fees
Feb 23 - Feb 24
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

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

10.0 out of 10, Exceptional, (151)
"We had an amazing stay - and Greg was absolutely phenomenal with communication - especially with providing information on plowing during a snow storm while we were there. The property was gorgeous and just a few minutes away from Wyndham Mountain. The property was very clean and huge for the great price. We were able to have a wellness retreat and the amenities were great! "
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

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

9.8 out of 10, Exceptional, (9)
"We had the best time! The property was perfect! Plenty of bedrooms and bathrooms plus gathering spaces galore ! The kitchen was stocked with all the necessities. We had 6 children age 8 and under so the outside property was perfect. Just enough snow for a snowman and some sledding! Plus an enormous deck and wrap around porch. There was a laundry and plenty of towels , pillows and cozy blankets! We will definitely be back! "
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.