A winding road through a forest with autumn foliage, a rocky cliff on the right, and a mountain in the background.

Search Chalets in Windham from CA $240

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Windham chalets

A snowy landscape with a wooden deck and a house in the background.

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.
The price is CA $557
CA $945 total
includes taxes & fees
Sep 8 - Sep 9
Beautiful Windham Chalet 2 minutes to Town and the Mountain
An outdoor dining area with a grill, wooden table, wicker chairs, and a stone wall backdrop.

2. Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit

Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
Windham
10.0 out of 10, Exceptional, (9 reviews)
"Great for two families. The main room is awesome to hang out in. The house is clean, and the owner super helpful."
United States
Michael L.
The price is CA $1,260
CA $2,424 total
includes taxes & fees
Sep 14 - Sep 15
Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
A log cabin with a porch, a staircase, and a garage.

3. 1 Mile From Ski Slope and Festivals - 125 Nightly Fee

1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Hunter
9.4 out of 10, Exceptional, (31 reviews)
"Everything was fantastic.We would recommend the place to everyone."
United States
Mary C.
The price is CA $180
CA $304 total
includes taxes & fees
Sep 3 - Sep 4
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
A picnic setup with a wine glass, bottle, cheese, tomatoes, and grapes on a wooden table with a view of a grassy field and hills.

4. 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.
The price is CA $330
CA $1,117 total
includes taxes & fees
Sep 2 - Sep 3
Relaxing Mountain Hideaway - Hot Tub & Outdoors
A wooden deck with wicker chairs and a table, a wooden cabin, and a neatly trimmed hedge.

5. Jessie's Harvest House

Jessie's Harvest House
Tannersville
The price is CA $182
CA $298 total
includes taxes & fees
Oct 1 - Oct 2
Jessie's Harvest House
A wooden deck with wicker chairs and a table, a wooden cabin, and a neatly trimmed hedge.

6. Jessie's Harvest House

Jessie's Harvest House
Tannersville
8.8 out of 10, Excellent, (5 reviews)
"cute little spot! very nice place to stay"
United States
David R.
The price is CA $164
CA $277 total
includes taxes & fees
Sep 16 - Sep 17
Jessie's Harvest House
A wooden deck with wicker chairs and a table, a wooden cabin, and a neatly trimmed hedge.

7. Jessie's Harvest House Suite

Jessie's Harvest House Suite
Tannersville
9.0 out of 10, Wonderful, (8 reviews)
"Everything's done online and great food within mins from the stay. Very accommodating and pet friendly! Super easy to communicate and fast response no matter the time! "
United States
Jennie D.
The price is CA $130
CA $240 total
includes taxes & fees
Sep 2 - Sep 3
Jessie's Harvest House Suite
A cabin with a deck, surrounded by trees with autumn foliage.

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

HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin
Fleischmanns
9.6 out of 10, Exceptional, (84 reviews)
"Great amenities and location!"
United States
Angeli F.
The price is CA $173
CA $398 total
includes taxes & fees
Sep 8 - Sep 9
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin
A wooden deck with wicker chairs and a table, a wooden cabin, and a neatly trimmed hedge.

9. Jessie's Harvest House

Jessie's Harvest House
Tannersville
The price is CA $182
CA $298 total
includes taxes & fees
Oct 1 - Oct 2
Jessie's Harvest House
A snow-covered deck with a fire pit, a chair, and a table with drinks and a game box.

10. Cabin w/ Mountain Views, Hot Tub, AC, Pet + Family Friendly, WFH, Fireplace

Cabin w/ Mountain Views, Hot Tub, AC, Pet + Family Friendly, WFH, Fireplace
Lexington
10.0 out of 10, Exceptional, (4 reviews)
"We enjoyed a week here with our two daughters and their husbands. The chalet was fantastic, as was the scenery. highly recommend this location."
Canada
Steven K.
The price is CA $838
CA $1,377 total
includes taxes & fees
Sep 20 - Sep 21
Cabin w/ Mountain Views, Hot Tub, AC, Pet + Family Friendly, WFH, Fireplace
A large, two-story house with a steeply pitched roof, a wooden deck, and a stone foundation.

11. 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
10.0 out of 10, Exceptional, (26 reviews)
"Room was spotless and amenities were great."
United States
Richard
The price is CA $697
CA $1,335 total
includes taxes & fees
Sep 3 - Sep 4
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.
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Top Windham Hotel Reviews

Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

8/10 Good
"Clean comfortable room and restaurant."
Richard 1-night trip
Posted 18 hours ago
Howard Johnson by Wyndham Saugerties

Find out more about Windham

Windham Chalets information

Number of reviews
89
Accommodation
61 Chalets
Lowest Price
CA $240
Highest Price
CA $2,424

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