Windham Chalets

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Chalets in Windham

1 Mile From Ski Slope and Festivals - 125 Nightly Fee

1 Mile From Ski Slope and Festivals - 125 Nightly Fee

Hunter NY
$206 nightly
The price is $222 total per night
$222 total
Oct 27 - Oct 28
Total with taxes and fees
With a stay at this chalet in Hunter, you'll be next to a golf course, within a 5-minute drive of Hunter Mountain and Catskill State Park.
Pool
Hot Tub
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

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

Fleischmanns NY
With a stay at this chalet in Fleischmanns, you'll be in the mountains, within a 10-minute drive of Belleayre Mountain Ski Center and Catskill State Park.
Hot Tub
Kitchen
Jessie's Harvest House

Jessie's Harvest House

Tannersville NY
$191 nightly
The price is $202 total per night
$202 total
Oct 27 - Oct 28
Total with taxes and fees
When you stay at this chalet in Tannersville, you'll be in the mountains, within a 10-minute drive of Hunter Mountain and Kaaterskill Falls.
Air conditioning
Outdoor Space
CHALET with INDOOR POOLHOUSE base of HUNTER mountain

CHALET with INDOOR POOLHOUSE base of HUNTER mountain

Lanesville NY
With a stay at this chalet in Hunter, you'll be within a 10-minute drive of Hunter Mountain and Catskill State Park.
Pool
Kitchen
Jessie's Harvest House

Jessie's Harvest House

Tannersville NY
$190 nightly
The price is $201 total per night
$201 total
Oct 27 - Oct 28
Total with taxes and fees
When you stay at this chalet in Tannersville, you'll be in the mountains, within a 10-minute drive of Hunter Mountain and Kaaterskill Falls.
Air conditioning
Laundry
Cozy Silo with Sunset Mountain Views near Woodstock

Cozy Silo with Sunset Mountain Views near Woodstock

Willow NY
With a stay at this chalet in Willow, you'll be in the mountains, just a 1-minute walk from Catskill State Park and 14 minutes by foot from James Cox Gallery.
Kitchen
Pet friendly
Secluded Chalet in the Northern Catskills with FIBER Internet and EV hookup

Secluded Chalet in the Northern Catskills with FIBER Internet and EV hookup

Summit NY
Located in Summit, this chalet is on a lake, within a 15-minute drive of Summit Town Hall and Mallet Pond State Forest.
Kitchen
Pet friendly
Relaxing Mountain Hideaway - Hot Tub & Outdoors

Relaxing Mountain Hideaway - Hot Tub & Outdoors

Hensonville NY
$635 nightly
The price is $686 total per night
$686 total
Nov 1 - Nov 2
Total with taxes and fees
When you stay at this chalet in Hensonville, you'll be in the mountains, within a 15-minute drive of Hunter Mountain and Windham Mountain Resort.
Hot Tub
Kitchen
Jessie's Harvest House

Jessie's Harvest House

Tannersville NY
$191 nightly
The price is $202 total per night
$202 total
Oct 27 - Oct 28
Total with taxes and fees
When you stay at this chalet in Tannersville, you'll be in the mountains, within a 10-minute drive of Hunter Mountain and Kaaterskill Falls.
Air conditioning
Outdoor Space
Le View Chalet- HotTub, Sauna, Fire Pit, Geodome

Le View Chalet- HotTub, Sauna, Fire Pit, Geodome

Maplecrest NY
With a stay at this chalet in Maplecrest, you'll be in the mountains, within a 15-minute drive of Windham Mountain Resort and Catskill State Park.
Pool
Hot Tub
Catskill getaway near Woodstock, Hunter, Hudson

Catskill getaway near Woodstock, Hunter, Hudson

Palenville NY
With a stay at this chalet in Palenville, you'll be within a 15-minute drive of Kaaterskill Falls and Vinnie's Farm Market.
Kitchen
Washer
The Hunter Chalet

The Hunter Chalet

Hunter NY
With a stay at this chalet in Hunter, you'll be in the mountains, within a 15-minute drive of Hunter Mountain and Catskill State Park.
Hot Tub
Washer
Don't see what you're looking for?
See all available properties in Windham
View all properties
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.

Windham Chalets essential information

Accommodation
66 Chalets
Lowest Price
$201
Highest Price
$686
Popular accommodation
1 Mile From Ski Slope and Festivals - 125 Nightly Fee, HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin, Jessie's Harvest House, CHALET with INDOOR POOLHOUSE base of HUNTER mountain, Jessie's Harvest House, Cozy Silo with Sunset Mountain Views near Woodstock, Secluded Chalet in the Northern Catskills with FIBER Internet and EV hookup, Relaxing Mountain Hideaway - Hot Tub & Outdoors, Jessie's Harvest House, Le View Chalet- HotTub, Sauna, Fire Pit, Geodome, Catskill getaway near Woodstock, Hunter, Hudson, The Hunter Chalet

Top Picks