Search Chalets in Windham

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

Chalets in Windham

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Terrace/patio

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

9.8 out of 10, Exceptional, (22)
"We had an amazing trip, and the host was very responsive and helpful with everything. The house was great, had everything we needed, and the private ski run back to the property was really fun. Highly recommend this property and the best host we have ever had!! Favoriting this place for a future stay!"
The price is AED 278
AED 1,298 total
includes taxes & fees
6 Oct - 7 Oct
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Fall into Cozy at Bigfoot Chalet
Exterior

Fall into Cozy at Bigfoot Chalet

2.0 star property
10.0 out of 10, Exceptional, (14)
"We only stayed on night while exploring the area, but it was so lovely! The more we looked, the more cute, and thoughtful elements we sae. Would definitely come back!"
The price is AED 731
AED 1,748 total
includes taxes & fees
19 Oct - 20 Oct
Fall into Cozy at Bigfoot Chalet
Mountain Chalet mins from Mt Snow Skiing/hiking
Exterior

Mountain Chalet mins from Mt Snow Skiing/hiking

9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
The price is AED 500
AED 1,651 total
includes taxes & fees
27 Oct - 28 Oct
Mountain Chalet mins from Mt Snow Skiing/hiking
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Exterior

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

10.0 out of 10, Exceptional, (2)
"Our stay was amazing! The cabin was perfect especially when the weather did not cooperate. It was clean and cozy. We enjoyed board games, PAC-MAN, cooking, and relaxing on the nice sofa. Very dog friendly:)"
The price is AED 606
AED 1,577 total
includes taxes & fees
29 Oct - 30 Oct
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Exterior

Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

10.0 out of 10, Exceptional, (4)
"We had a great time at the Chalet. Great accommodations Jennifer made sure we had everything we needed She went above and beyond to accommodate our group. "
The price is AED 2,020
AED 3,673 total
includes taxes & fees
6 Oct - 7 Oct
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Private Chalet: walk to hiking/biking trails and golf course
Exterior

Private Chalet: walk to hiking/biking trails and golf course

2.0 star property
9.6 out of 10, Exceptional, (5)
"We spent the week, excellent location and the home was exactly as described in listing."
The price is AED 731
AED 2,171 total
includes taxes & fees
13 Oct - 14 Oct
Private Chalet: walk to hiking/biking trails and golf course
Bromley Aframe - King Master Bed, Wood Fireplace
Exterior

Bromley Aframe - King Master Bed, Wood Fireplace

9.6 out of 10, Exceptional, (14)
"This house was great for my family's spring vacation. The stream was beautiful and relaxing. "
Bromley Aframe - King Master Bed, Wood Fireplace
Stylish Farmhouse - Close to Ski, Golf + Hot Tub
Terrace/patio

Stylish Farmhouse - Close to Ski, Golf + Hot Tub

10.0 out of 10, Exceptional, (6)
"Very large, bright and completely remodeled. Plenty of space for a large family to hang out in the kitchen area and living room."
The price is AED 735
AED 2,298 total
includes taxes & fees
8 Oct - 9 Oct
Stylish Farmhouse - Close to Ski, Golf + Hot Tub
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Terrace/patio

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

10.0 out of 10, Exceptional, (13)
"Clean, great location. Pet friendly and well thought out. "
The price is AED 735
AED 1,648 total
includes taxes & fees
27 Oct - 28 Oct
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
8 minutes to Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private
Outdoor spa tub

8 minutes to Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private

10.0 out of 10, Exceptional, (20)
"Whole hearted recommend this property for anyone looking to stay in the area. Great location, great atmosphere and most importantly great house. 10/10 hidden gem. "
The price is AED 655
AED 2,238 total
includes taxes & fees
14 Oct - 15 Oct
8 minutes to Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private
New! 7 min to Stratton access road, HotTub, Sauna EV
Exterior

New! 7 min to Stratton access road, HotTub, Sauna EV

The price is AED 922
AED 1,928 total
includes taxes & fees
28 Oct - 29 Oct
New! 7 min to Stratton access road, HotTub, Sauna EV
Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres
Exterior

Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres

10.0 out of 10, Exceptional, (5)
"We had an amazing stay. It was the perfect location for 4 couples. The owners were super responsive. Amenities were great (our only kitchen recommendation is a non-glass cutting board and individual salt and pepper shakers). Would love to stay again in the summer next time! "
The price is AED 1,109
AED 2,528 total
includes taxes & fees
3 Nov - 4 Nov
Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres
Charming Chalet w. Hot Tub - 1 mile to Mt. Snow
Terrace/patio

Charming Chalet w. Hot Tub - 1 mile to Mt. Snow

10.0 out of 10, Exceptional, (13)
"The Chalet was perfect for my families stay in Vermont. We spent the week hiking, exploring the waterfalls and all the towns. The house had everything we needed after a day of hiking. All the games were great too. The house was very clean and well maintained. Thank you for allowing us to stay at The Chalet!"
The price is AED 1,098
AED 2,652 total
includes taxes & fees
7 Oct - 8 Oct
Charming Chalet w. Hot Tub - 1 mile to Mt. Snow
Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus
Outdoor spa tub

Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus

10.0 out of 10, Exceptional, (8)
"Communication was exceptional and property was as described. Great location, comfortable beds, well supplied and super easy check-in and checkout. "
The price is AED 655
AED 2,450 total
includes taxes & fees
14 Oct - 15 Oct
Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus
NEW Private Chalet - 4 mins to Mt Snow
Exterior

NEW Private Chalet - 4 mins to Mt Snow

10.0 out of 10, Exceptional, (1)
The price is AED 764
AED 2,266 total
includes taxes & fees
6 Oct - 7 Oct
NEW Private Chalet - 4 mins to Mt Snow
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windham Hotel Reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"I loved our stay because it was very clean, comfortable and had the most beautiful view of the bay! The pool is huge and we even had a patio off of our room. We were just 5 minutes from Canton with great restaurants and shops. I also recommend going on a sailing excursion! "
Susan 2-night trip
Posted 1 day ago
Pointe at Castle Hill Resort