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Find Chalets in Windham County, VT from $368

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In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Top Cities in Windham County

We were pretty impressed with this. Never seen a frozen body of water strong enough for all of this activity!
ChaletsChalets

Brattleboro

Brattleboro

Chalets in Windham County

Exterior
Beautiful- Ski/Golf home, Hot tub, mins to MTN

Beautiful- Ski/Golf home, Hot tub, mins to MTN

Wilmington
8.4 out of 10, Very Good, (5)
"we loved our stay there! having a home where you can cook, have everything you need to do so helps so much"
United States
Dawn F.
Beautiful- Ski/Golf home, Hot tub, mins to MTN
Property grounds
Beautiful Lodging at Mount Snow with Hot Tub on Deck

Beautiful Lodging at Mount Snow with Hot Tub on Deck

Wilmington
9.4 out of 10, Exceptional, (42)
"My family and I loved our stay. This cabin had everything we needed and more. One thing we do wish we had was fans in the upstairs rooms, as we stayed in the summer time and it did get quite hot up there. The owners were very helpful, and amazing with communication. We would absolutely love to stay here again one day! "
United States
lizzie m.
Beautiful Lodging at Mount Snow with Hot Tub on Deck
Property grounds
Private 6 bedroom Chalet 5min to Mt Snow

Private 6 bedroom Chalet 5min to Mt Snow

Dover
9.8 out of 10, Exceptional, (14)
"Great stay and successful bachelor party, host was very accommodating with check-in & check-out timing. Several phenomenal golf courses within 10 minutes of the property, gorgeous views! "
United States
Nick B.
Private 6 bedroom Chalet 5min to Mt Snow
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, (14)
"Perfect weekend getaway "
United States
Seth G.
$344 nightly
The price is $389
Dec 8 - Dec 9
Total with taxes and fees
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Terrace/patio
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, (22)
"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.
$398 nightly
The price is $450
Dec 15 - Dec 16
Total with taxes and fees
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Exterior detail
Modern Lux Cabin w/ Mtn Views | Fire Pit

Modern Lux Cabin w/ Mtn Views | Fire Pit

Stratton
10.0 out of 10, Exceptional, (1)
"Tommy was a fantastic host!"
United States
Kelsey H.
Modern Lux Cabin w/ Mtn Views | Fire Pit
Property grounds
Alpine Chalet with outdoor Jacuzzi 1 mile from ski lifts

Alpine Chalet with outdoor Jacuzzi 1 mile from ski lifts

Dover
9.8 out of 10, Exceptional, (39)
"House was clean and comfortable and would love to stay again next season! "
United States
Steven L.
Alpine Chalet with outdoor Jacuzzi 1 mile from ski lifts
Interior
Two Bedroom Chalet, Charming, Quiet, River Front

Two Bedroom Chalet, Charming, Quiet, River Front

Jamaica
9.4 out of 10, Exceptional, (75)
"Loved the location and the house was great. All amenities were as described. Great host. Highly recommend. "
United States
Brian E.
Two Bedroom Chalet, Charming, Quiet, River Front
Exterior detail
Vermont winter chalet near Mount Snow and Wilmington

Vermont winter chalet near Mount Snow and Wilmington

West Dover
10.0 out of 10, Exceptional, (23)
"Great place, close to everything, all amenities and most importantly great hosts!"
United States
Michael S.
Vermont winter chalet near Mount Snow and Wilmington
Exterior
Mountain Chalet mins from Mt Snow Skiing/hiking

Mountain Chalet mins from Mt Snow Skiing/hiking

East Dover
9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
$353 nightly
The price is $398
Dec 7 - Dec 8
Total with taxes and fees
Mountain Chalet mins from Mt Snow Skiing/hiking
Outdoor spa tub
Hot Tub, Game Room, Fire Pit, Dog friendly, 8 minutes to Ski Mount Snow

Hot Tub, Game Room, Fire Pit, Dog friendly, 8 minutes to Ski Mount Snow

West Dover
10.0 out of 10, Exceptional, (20)
"Had a delightful time here for the Holiday. Quiet place which held us all comfortably! Easy to get to the places we wanted to go to and was well maintained. Communication with the hosts was fantastic."
United States
Jeannine A.
$497 nightly
The price is $562
Dec 10 - Dec 11
Total with taxes and fees
Hot Tub, Game Room, Fire Pit, Dog friendly, 8 minutes to Ski Mount Snow
Exterior
Private cabin: 7 mins to slopes, wood fireplace

Private cabin: 7 mins to slopes, wood fireplace

2.0 star property
Dover
9.8 out of 10, Exceptional, (6)
"We spent the week, excellent location and the home was exactly as described in listing."
United States
Chris R.
$744 nightly
The price is $841
Dec 10 - Dec 11
Total with taxes and fees
Private cabin: 7 mins to slopes, wood fireplace
Outdoor dining
COZY TREE LIKE HOUSE. WALK TO MARKET & REST. LOW RATES. 1 MILE TO MT SNOW.

COZY TREE LIKE HOUSE. WALK TO MARKET & REST. LOW RATES. 1 MILE TO MT SNOW.

West Dover
9.8 out of 10, Exceptional, (35)
"Clean, spacious and perfect location!!"
United States
Anonymous traveler
COZY TREE LIKE HOUSE. WALK TO MARKET & REST. LOW RATES. 1 MILE TO MT SNOW.
Exterior
Chimney Hill 15 mins to Mt Snow, Clubhouse w/indoor pool, VAST trail to house

Chimney Hill 15 mins to Mt Snow, Clubhouse w/indoor pool, VAST trail to house

Wilmington
9.6 out of 10, Exceptional, (40)
"Joe was nice and easy to talk to. Neighbors were all friendly and the pool area/clubhouse was nice, clean, and inviting. We enjoyed the duck pond for some small easy fishing. Friendly, cool town center about 14 minutes away. I think this place was perfect for the price. "
United States
David Q.
Chimney Hill 15 mins to Mt Snow, Clubhouse w/indoor pool, VAST trail to house
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, (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. "
United States
Chris I.
$625 nightly
The price is $706
Jan 6 - Jan 7, 2026
Total with taxes and fees
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Exterior
Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room

Guilford
$336 nightly
The price is $368
Dec 7 - Dec 8
Total with taxes and fees
Vikings Villages Resort - Double Bed Room
Terrace/patio
New Listing! Golf/Ski home w/SteamRoom & Hot Tub

New Listing! Golf/Ski home w/SteamRoom & Hot Tub

Dover
10.0 out of 10, Exceptional, (7)
"Beautiful house and property."
United States
Arthur H.
New Listing! Golf/Ski home w/SteamRoom & Hot Tub
Property grounds
New! Mt Snow Chalet w/land, privacy, relaxation

New! Mt Snow Chalet w/land, privacy, relaxation

Dover
8.6 out of 10, Excellent, (7)
"Excellent location to skiing Spacious rooms Plenty of towels Kitchen stocked with appliances Close to market "
United States
Heather F.
New! Mt Snow Chalet w/land, privacy, relaxation
Terrace/patio
Spacious Vermont Chalet for Group Getaways

Spacious Vermont Chalet for Group Getaways

West Dover
10.0 out of 10, Exceptional, (3)
"This property had plenty of space! We had 9 adults and 2 dogs. Shuffleboard and hot tub were great bonuses! Management was very attentive and responded within 10 minutes to any inquiries even once we checked in. House was clean, spacious and perfectly located."
United States
Kimberly M.
Spacious Vermont Chalet for Group Getaways
Exterior
Mountain Chalet mins to Mt Snow - Clubhouse w/pool, mins to town for dining out.

Mountain Chalet mins to Mt Snow - Clubhouse w/pool, mins to town for dining out.

Wilmington
9.6 out of 10, Exceptional, (14)
"Perfect for a family of four, close to Mt Snow"
United States
Elisabeth G.
Mountain Chalet mins to Mt Snow - Clubhouse w/pool, mins to town for dining out.
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 County Hotel Reviews

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"The staff are amazing! So friendly and welcoming. The lodge is so cute! The rooms were spotless and the hottub sparkling clean. The shuttle service until 10 pm was fantastic and the shuttle driver was very nice. We can't wait to visit again! "
Barbara 1-night trip
Posted 1 day ago
The Black Bear Lodge at Stratton Mountain Resort

Find out more about Windham County

Windham County Chalets information

Number of reviews
360
Accommodation
71 Chalets
Lowest Price
$368
Highest Price
$841

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