Windham Chalets

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Our top choices for Windham chalets

1. Beautiful Windham Chalet 2 minutes to Town and the Mountain

Beautiful Windham Chalet 2 minutes to Town and the Mountain
Windham
10.0 out of 10, Exceptional, (3 reviews)
"Very easy to check in and check out. Very excellent instructions and welcoming atmosphere. "
United States
John K.
$583 nightly
The price is $629
Nov 17 - Nov 18
Total with taxes and fees
Beautiful Windham Chalet 2 minutes to Town and the Mountain

2. Relaxing Mountain Hideaway - Hot Tub & Outdoors

Relaxing Mountain Hideaway - Hot Tub & Outdoors
Hensonville
10.0 out of 10, Exceptional, (3 reviews)
"Great house and great host! Very convenient location particularly to Windham Mountain. "
United States
Kyrill A.
$551 nightly
The price is $595
Nov 16 - Nov 17
Total with taxes and fees
Relaxing Mountain Hideaway - Hot Tub & Outdoors

3. Jessie's Harvest House

Jessie's Harvest House
Tannersville
8.4 out of 10, Very good, (7 reviews)
"cute little spot! very nice place to stay"
United States
David R.
$181 nightly
The price is $191
Nov 15 - Nov 16
Total with taxes and fees
Jessie's Harvest House

4. Jessie's Harvest House

Jessie's Harvest House
Tannersville
2.0 out of 10, (1 review)
"We pulled up to a restaurant inn with not a soul in sight. The restaurant was closed with a for sale Realastate sign outside. There place had broken windows and a side back door to access . We walked in to find a dark room with an old piano . We went upstairs to see the room and the only thing in the rooms posted was the white sheets and blankets . There was a small area with a microwave outside our door . The pictures had an outside sitting for guests that was not the case . We left and ended...
United States
Genine B.
$181 nightly
The price is $191
Nov 13 - Nov 14
Total with taxes and fees
Jessie's Harvest House

5. Jessie's Harvest House

Jessie's Harvest House
Tannersville
$180 nightly
The price is $190
Nov 13 - Nov 14
Total with taxes and fees
Jessie's Harvest House

6. Jessie's Harvest House

Jessie's Harvest House
Tannersville
8.0 out of 10, Very good, (1 review)
$181 nightly
The price is $191
Nov 13 - Nov 14
Total with taxes and fees
Jessie's Harvest House

7. Jessie's Harvest House

Jessie's Harvest House
Tannersville
$180 nightly
The price is $190
Nov 13 - Nov 14
Total with taxes and fees
Jessie's Harvest House

8. Jessie's Harvest House Suite

Jessie's Harvest House Suite
Tannersville
9.0 out of 10, Wonderful, (8 reviews)
"Perfect, clean space for a quick overnight. Very close proximity to all that the area has to offer."
United States
Matthew M.
$177 nightly
The price is $187
Dec 8 - Dec 9
Total with taxes and fees
Jessie's Harvest House Suite

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

Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre
Big Indian
9.8 out of 10, Exceptional, (30 reviews)
"Room was spotless and amenities were great."
United States
Richard
$691 nightly
The price is $774
Nov 16 - Nov 17
Total with taxes and fees
Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre
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.

Learn more about Windham

Nestled in the Catskills, this mountain town transforms from a powdery ski paradise to a lush hiking haven with seasons. Visit Windham Mountain for thrilling slopes in winter or explore the scenic Rail Trail when summer's wildflowers frame perfect mountain views.

Two skiers on a snowy slope with a valley and mountains in the background.

Top reviews in Windham

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