Search Chalets in Windham from CA $615

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Check prices for these dates

In two weeks
Mar 6 - Mar 8
In two months
Apr 17 - Apr 19
In three months
May 15 - May 17
In four months
Jun 12 - Jun 14

Our top choices for Windham chalets

Exterior

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Plymouth
10.0 out of 10, Exceptional, (14 reviews)
"We had a great stay! Beautiful spot tucked in the woods. Great host communication!"
United States
Julie-Anne B.
The price is CA $431
CA $990 total
includes taxes & fees
Feb 24 - Feb 25
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Exterior

8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly

8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
West Dover
10.0 out of 10, Exceptional, (23 reviews)
"Wonderful time..the home was very spacious and comfortable..great location!"
United States
Ellen P.
The price is CA $569
CA $1,265 total
includes taxes & fees
Feb 22 - Feb 23
8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
9.8 out of 10, Exceptional, (10 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is CA $171
CA $615 total
includes taxes & fees
Feb 22 - Feb 23
Chalet Mount Snow/Stratton Skiing/hiking
Exterior

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

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.8 out of 10, Exceptional, (23 reviews)
"Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. "
United States
SZU YIN C.
The price is CA $185
CA $651 total
includes taxes & fees
Mar 2 - Mar 3
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Terrace/patio

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

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Wardsboro
10.0 out of 10, Exceptional, (19 reviews)
"We had an awesome time here. The property was well stocked with essentials, affordable us some opportunity to unwind, explore the creek, and hang out with the fire pit, board games, and the kids enjoyed the ridge racer arcade. Would absolutely come back!"
United States
Joseph R.
The price is CA $260
CA $616 total
includes taxes & fees
Mar 10 - Mar 11
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Exterior

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

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Wardsboro
10.0 out of 10, Exceptional, (5 reviews)
"Impressively clean house! The owners were great to deal with and very responsive. Would certainly recommend to anyone traveling in the area."
United States
Kristen T.
The price is CA $308
CA $749 total
includes taxes & fees
Mar 10 - Mar 11
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Exterior

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

Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Dover
10.0 out of 10, Exceptional, (7 reviews)
"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. "
United States
Chris I.
The price is CA $753
CA $1,369 total
includes taxes & fees
Mar 9 - Mar 10
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Outdoor dining

Private cabin: 7 mins to slopes, wood fireplace

Private cabin: 7 mins to slopes, wood fireplace
Dover
9.8 out of 10, Exceptional, (6 reviews)
"We spent the week, excellent location and the home was exactly as described in listing."
United States
Chris R.
The price is CA $472
CA $1,078 total
includes taxes & fees
Mar 2 - Mar 3
Private cabin: 7 mins to slopes, wood fireplace
Exterior

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

Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres
Stratton
10.0 out of 10, Exceptional, (5 reviews)
"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! "
United States
Nicholas D.
The price is CA $471
CA $1,112 total
includes taxes & fees
Mar 10 - Mar 11
Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres
Terrace/patio

A Charming Chalet with Hot Tub 1 Mile to Mt. Snow

A Charming Chalet with Hot Tub 1 Mile to Mt. Snow
Dover
10.0 out of 10, Exceptional, (15 reviews)
"This place was absolutely amazing! The pictures didn’t do this place justice. The ambience of the deck at night was magical. "
United States
Kaymari T.
The price is CA $615
CA $1,253 total
includes taxes & fees
Mar 4 - Mar 5
A Charming Chalet with Hot Tub 1 Mile to Mt. Snow
Exterior

Spacious Chalet Near Stratton and Mt. Snow w/Indoor Hot Tub, Fireplace, Firepit

Spacious Chalet Near Stratton and Mt. Snow w/Indoor Hot Tub, Fireplace, Firepit
Wardsboro
10.0 out of 10, Exceptional, (3 reviews)
"Everything was great!"
United States
emilie d.
The price is CA $780
CA $1,404 total
includes taxes & fees
Mar 18 - Mar 19
Spacious Chalet Near Stratton and Mt. Snow w/Indoor Hot Tub, Fireplace, Firepit
Exterior

New Stratton Ski Haus: A-Frame Hot Tub Sauna EV Privacy 1Gbps Manchester Okemo

New Stratton Ski Haus: A-Frame Hot Tub Sauna EV Privacy 1Gbps Manchester Okemo
Jamaica
10.0 out of 10, Exceptional, (2 reviews)
"Couldn't be better! Outstanding! We had our family holiday ski trip from Dec 25-29th,2025. The amenities were second to none. The hot tub, sauna and fire pit made the winter warm! The house was clean comfortable and very cozy. The kitchen was extremely well appointed (sharp knives!). The staples available (coffee, tea, oil, spices etc.) were high quality and the best I've ever experienced in a short term rental. The beds and bedding were very comfortable! Most immortality the hosts were very...
United States
Laird N.
The price is CA $706
CA $1,531 total
includes taxes & fees
Feb 23 - Feb 24
New Stratton Ski Haus: A-Frame Hot Tub Sauna EV Privacy 1Gbps Manchester Okemo
Outdoor spa tub

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

Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus
Dover
10.0 out of 10, Exceptional, (11 reviews)
"Helpful, fun and warm. "
United States
Anthony S.
The price is CA $548
CA $1,503 total
includes taxes & fees
Feb 25 - Feb 26
Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus
Exterior

NEW Private Chalet - 4 mins to Mt Snow

NEW Private Chalet - 4 mins to Mt Snow
Dover
10.0 out of 10, Exceptional, (2 reviews)
"Mary and Adam were absolutely lovely hosts! From the initial booking to check-in and throughout our stay, they were incredibly responsive. The house was fantastic—completely updated, with a fully equipped kitchen, spacious bedrooms, and a beautiful living area with a cozy fireplace.Our only regret is that we couldn’t stay longer. Thank you, Mary and Adam, for a wonderful stay!"
United States
Patricia N.
The price is CA $336
CA $901 total
includes taxes & fees
Feb 23 - Feb 24
NEW Private Chalet - 4 mins to Mt Snow
Property grounds

Green Mountain Manor - Ski and Summer Chalet

Green Mountain Manor - Ski and Summer Chalet
Winhall
9.8 out of 10, Exceptional, (7 reviews)
"Beautiful property less than 5 minutes from Stratton!! Very private and secluded"
United States
Jay T.
The price is CA $2,812
CA $4,295 total
includes taxes & fees
Feb 21 - Feb 22
Green Mountain Manor - Ski and Summer Chalet
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

The Manchester View

The Manchester View

10/10 Excellent
"Clean, comfortable room."
Robert 1-night trip
Posted 2 days ago
The Manchester View

Find out more about Windham

Windham Chalets information

Number of reviews
140
Accommodation
102 Chalets
Lowest Price
CA $615
Highest Price
CA $4,295

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