Search Chalets in Windham from CA $149

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Windham Chalets

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

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 $195
CA $382 total
includes taxes & fees
Aug 14 - Aug 15
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin
Jessie's Harvest House
Bar (on property)

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 $149
CA $262 total
includes taxes & fees
Aug 7 - Aug 8
Jessie's Harvest House
Stunning Catskills Cabin Getaway, facing BelleAyre
Smart TV, fireplace, table tennis, video library

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

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
Fridge, microwave, oven, stovetop

1 Mile From Ski Slope and Festivals - 125 Nightly Fee

10.0 out of 10, Exceptional, (9)
"Perfect, cozy place to stay for a ski weekend!"
The price is CA $170
CA $294 total
includes taxes & fees
Aug 7 - Aug 8
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Cozy Silo with Sunset Mountain Views near Woodstock
Exterior

Cozy Silo with Sunset Mountain Views near Woodstock

9.8 out of 10, Exceptional, (13)
"What a great place! Comfortable, quiet, and secluded. A wonderful place for a getaway. Thank you!"
Cozy Silo with Sunset Mountain Views near Woodstock
Beautiful Chalet, mins to Hunter/Windham slopes
Fireplace

Beautiful Chalet, mins to Hunter/Windham slopes

9.8 out of 10, Exceptional, (17)
"Easy trip to the mountain. Beautiful view. Plenty of room. "
Beautiful Chalet, mins to Hunter/Windham slopes
Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre
Exterior

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

10.0 out of 10, Exceptional, (16)
"House was great, hosts were very accommodating. Location was perfect to get to Belleayre Mountain. "
The price is CA $557
CA $1,152 total
includes taxes & fees
Aug 11 - Aug 12
Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre
Jessie's Harvest House
Outdoor dining

Jessie's Harvest House

Jessie's Harvest House
Chalet w/HOT TUB & OUTDOOR TV, Fire Pit, Pool Nearby, Prvt. trail & playground!
Pool

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

10.0 out of 10, Exceptional, (21)
"Nice place for a skiing holiday"
Chalet w/HOT TUB & OUTDOOR TV, Fire Pit, Pool Nearby, Prvt. trail & playground!
Rustic Mountain view Cabin 5 mins to Ski Area!
Property grounds

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!
Catskill Chalet: Serene Mountain Escape
Terrace/patio

Catskill Chalet: Serene Mountain Escape

10.0 out of 10, Exceptional, (11)
"Cozy home located 5 minutes from bellarye mt. Taco bar next to house was a plus."
Catskill Chalet: Serene Mountain Escape
Jessie's Harvest House
Outdoor dining

Jessie's Harvest House

The price is CA $149
CA $262 total
includes taxes & fees
Aug 7 - Aug 8
Jessie's Harvest House
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. 5 min from Windham Ski
Fridge, microwave, oven, stovetop

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 $1,033
CA $2,022 total
includes taxes & fees
Aug 12 - Aug 13
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
Living area

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
The Hunter Chalet
Exterior

The Hunter Chalet

10.0 out of 10, Exceptional, (3)
"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
Never Lonesome Hunter: Smart 4bd Getaway near Mtn
Exterior

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
Never Lonesome Woodland Valley: Cozy 2bd Cottage!
Fridge, microwave, oven, stovetop

Never Lonesome Woodland Valley: Cozy 2bd Cottage!

9.4 out of 10, Exceptional, (9)
"The place was beautiful, spacious and cozy. Highly recommend it if you are looking for a quiet and relaxing time. "
Never Lonesome Woodland Valley: Cozy 2bd Cottage!
Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort
Exterior

Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

3.0 star property
Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort
Private Chalet less than 1 mile to Ski Resort
Exterior

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
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

Hotel Vienna

Hotel Vienna

10/10 Excellent
"The hotel was quiet ,hospitable and very comforting and welcoming staff.A peaceful,beautiful experience in a clean well kept ,very hospitable stay ."
Michelle 1-night trip
Posted 11 hours ago
Hotel Vienna