Search Chalets in Windham from CA $150

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Browse Select Windham Chalets

Our top choices for Windham chalets

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

9.6 out of 10, Exceptional, (53)
"Great location, Great Hot Tub, Great Catskills Mountains "
The price is CA $174
CA $357 total
includes taxes & fees
Sep 4 - Sep 5
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

Beautiful Chalet, mins to Hunter/Windham slopes

9.8 out of 10, Exceptional, (18)
"Easy trip to the mountain. Beautiful view. Plenty of room. "
Beautiful Chalet, mins to Hunter/Windham slopes

Jessie's Harvest House

10.0 out of 10, Exceptional, (1)
"For the location it is located it is a great place to stay. The rooms were clean and the beds and sheets were great. There is a restaurant on property so need to go far for something to eat. If I am ever in the area again I would definitely stay again. "
The price is CA $150
CA $266 total
includes taxes & fees
Aug 24 - Aug 25
Jessie's Harvest House

Mountain Chalet with Breathtaking Panoramic Views

9.8 out of 10, Exceptional, (173)
"Very pleasant stay close to markets, restaurant and ski resort. Lee was very responsive "
Mountain Chalet with Breathtaking Panoramic Views

Cozy Silo with Sunset Mountain Views near Woodstock

9.8 out of 10, Exceptional, (14)
"What a great place! Comfortable, quiet, and secluded. A wonderful place for a getaway. Thank you!"
Cozy Silo with Sunset Mountain Views near Woodstock

Stunning Catskills Cabin Getaway, facing BelleAyre

9.8 out of 10, Exceptional, (126)
"Great property for a ski trip to Belleayre. Close to the mountain. "
Stunning Catskills Cabin Getaway, facing BelleAyre

Chalet w/HOT TUB & OUTDOOR TV, Fire Pit, Pool Nearby, Prvt. trail & playground!

10.0 out of 10, Exceptional, (22)
"Nice place for a skiing holiday"
The price is CA $413
CA $829 total
includes taxes & fees
Aug 26 - Aug 27
Chalet w/HOT TUB & OUTDOOR TV, Fire Pit, Pool Nearby, Prvt. trail & playground!

Private Chalet less than 1 mile to Ski Resort

9.8 out of 10, Exceptional, (8)
"Cozy stay for our family of four!"
Private Chalet less than 1 mile to Ski Resort

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!

PRIVATE Heated Indoor Pool! 5 mins to Hunter Mtn and Summer Festivals

8.4 out of 10, Very good, (61)
"The home was nice and cozy. The owner was soo nice and soo responsive. Great place fo rent. "
PRIVATE Heated Indoor Pool! 5 mins to Hunter Mtn and Summer Festivals

1 Mile From Ski Slope and Festivals - 125 Nightly Fee

10.0 out of 10, Exceptional, (10)
"Perfect, cozy place to stay for a ski weekend!"
The price is CA $173
CA $300 total
includes taxes & fees
Aug 25 - Aug 26
1 Mile From Ski Slope and Festivals - 125 Nightly Fee

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

10.0 out of 10, Exceptional, (17)
"House was great, hosts were very accommodating. Location was perfect to get to Belleayre Mountain. "
The price is CA $561
CA $1,161 total
includes taxes & fees
Aug 27 - Aug 28
Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre

Jessie's Harvest House

The price is CA $150
CA $266 total
includes taxes & fees
Aug 24 - Aug 25
Jessie's Harvest House

Catskill Chalet: Serene Mountain Escape

10.0 out of 10, Exceptional, (12)
"Cozy home located 5 minutes from bellarye mt. Taco bar next to house was a plus."
Catskill Chalet: Serene Mountain Escape

Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. 5 min from Windham Ski

10.0 out of 10, Exceptional, (2)
"Great for two families. The main room is awesome to hang out in. The house is clean, and the owner super helpful."
The price is CA $1,040
CA $1,993 total
includes taxes & fees
Sep 8 - Sep 9
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. 5 min from Windham Ski

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

2.0 star property
7.6 out of 10, Good, (5)
"Nice big house that was accommodating for 4 families. Great location to Roxbury and Plattekill. Big sledding hill in backyard for kids. Would rent again."
Charming chalet with 5 bedrooms and WiFi, fitness room in peaceful Roxbury

Family-Friendly Windham Estate, Swimming Pond, Spa

9.8 out of 10, Exceptional, (37)
"Worked out perfectly"
Family-Friendly Windham Estate, Swimming Pond, Spa

Never Lonesome Hunter: Smart 4bd Getaway near Mtn

10.0 out of 10, Exceptional, (3)
"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

The Hunter Chalet

10.0 out of 10, Exceptional, (5)
"Great location and lots of space for a large group! Beautiful views and large yard for kids to run around. Comfortable beds and spacious rooms/bathrooms. "
The Hunter Chalet

Lakefront on the quiet side of main lake!

9.8 out of 10, Exceptional, (74)
"The property is very clean. The management is very responsive. We absolutely enjoyed our time."
Lakefront on the quiet side of main lake!
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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Top Windham Hotel Reviews