Find Chalets in Windham County, VT from $244

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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Top Cities in Windham County

Mount Snow
ChaletsChalets

West Dover

West Dover

Our top choices for Windham County chalets

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 reviews)
"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
Exterior

Cozy & Spacious Ski Condo 1 mile from Mount Snow VT

Cozy & Spacious Ski Condo 1 mile from Mount Snow VT
Dover
8.0 out of 10, Very Good, (1 review)
"Over the condo was nice. Great location, enough room and had basically what we needed. It felt a bit outdated and in some need of renovation. "
United States
Sean E.
Cozy & Spacious Ski Condo 1 mile from Mount Snow VT
Exterior

Skybarn Vermont | Pool, 100-Mile Views, Historic Barn

Skybarn Vermont | Pool, 100-Mile Views, Historic Barn
West Dover
10.0 out of 10, Exceptional, (1 review)
"I almost do NOT want to review this property because it was the absolute 100% BESTTTTT place I have stayed in all of my travels (which I can say we travel most every other week of most months!!!!! We absolutely loveeeeedddd this Was stunning felt as if it was a dream! Not sure how we were lucky enough to find this place and we were even allowed to bring our Dog who also NEVER wanted to leave!!! We would love to come back again and think we may have to because I’m not sure we could ever...
United States
Sandra V.
Skybarn Vermont | Pool, 100-Mile Views, Historic Barn
Exterior

Private 6 bedroom Chalet 5min to Mt Snow

Private 6 bedroom Chalet 5min to Mt Snow
Dover
9.8 out of 10, Exceptional, (16 reviews)
"Gorgeous house. Right next to the mountain. Gracious host."
United States
Clifford D.
Private 6 bedroom Chalet 5min to Mt Snow
Exterior

Modern Lux Cabin w/ Mtn Views | Fire Pit

Modern Lux Cabin w/ Mtn Views | Fire Pit
Stratton
10.0 out of 10, Exceptional, (1 review)
"Tommy was a fantastic host!"
United States
Kelsey H.
Modern Lux Cabin w/ Mtn Views | Fire Pit
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, (8 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.
$452 nightly
The price is $511
Jun 2 - Jun 3
Total with taxes and fees
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Exterior

Stratton Mountain Escape w Hot Tub|Deck|Projector

Stratton Mountain Escape w Hot Tub|Deck|Projector
East Jamaica
10.0 out of 10, Exceptional, (6 reviews)
"Great place. Clean and well taken care of. No issues over 6 days!"
United States
Justin S.
Stratton Mountain Escape w Hot Tub|Deck|Projector
Exterior

Chalet With Mountain View Steps From Shuttle

Chalet With Mountain View Steps From Shuttle
Dover
10.0 out of 10, Exceptional, (1 review)
"Clean, well maintained and a responsive host."
United States
Tim W.
Chalet With Mountain View Steps From Shuttle
Exterior

HotTub&GameRm&Traeger Smoker-15 min 2 Mt Snow, Across from Golf, 5 min to Lake

HotTub&GameRm&Traeger Smoker-15 min 2 Mt Snow, Across from Golf, 5 min to Lake
Wilmington
10.0 out of 10, Exceptional, (8 reviews)
"House was great for our family and perfect location for us to ski at hermitage club. Host was excellent with communication. "
United States
Devin P.
HotTub&GameRm&Traeger Smoker-15 min 2 Mt Snow, Across from Golf, 5 min to Lake
Property grounds

Beautiful Lodging at Mount Snow with Hot Tub on Deck

Beautiful Lodging at Mount Snow with Hot Tub on Deck
Wilmington
9.2 out of 10, Wonderful, (45 reviews)
"The cabin is wonderful. And as incredible as it sounds, it's much more beautiful and impressive in person. Surrounded by nature. Very peaceful and quiet. I recommend going for at least 3 days. You'll thank me later. And as a final piece of advice, since it's such a small town, I recommend doing your shopping early. Delivery is quite difficult, and there are no Ubers."
United States
Amet P.
Beautiful Lodging at Mount Snow with Hot Tub on Deck
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
9.6 out of 10, Exceptional, (26 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.
$390 nightly
The price is $441
May 10 - May 11
Total with taxes and fees
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Exterior

Chimney Hill Chalet w/full resort access, heated pools, trails, near lake & town

Chimney Hill Chalet w/full resort access, heated pools, trails, near lake & town
Wilmington
9.6 out of 10, Exceptional, (45 reviews)
"Great stay! We loved that everything was there that we needed and it was an easy, relaxing stay. The host was great!! "
United States
Melissa G.
Chimney Hill Chalet w/full resort access, heated pools, trails, near lake & town
Exterior

Chimney Hill Mtn Chalet w/resort access - heated pools, trails, near lake & town

Chimney Hill Mtn Chalet w/resort access - heated pools, trails, near lake & town
Wilmington
9.8 out of 10, Exceptional, (17 reviews)
"We had a great stay! The house was very cozy, the beds were super comfortable and there was plenty of room in the house for several adults and children; the kitchen was well stocked for all of our cooking needs. We appreciated the availability of snow sleds for the kids to use. The clubhouse was also very close by to use the pool and hot tub. Overall, we had a classic Vermont experience with daily snowfall, cold temps, and great skiing. Joe was a fantastic host who made the check-in and out...
United States
Alina Z.
Chimney Hill Mtn Chalet w/resort access - heated pools, trails, near lake & town
Exterior

Cozy 3 bedroom 2 bathroom chalet centrally located in Southern Vermont.

Cozy 3 bedroom 2 bathroom chalet centrally located in Southern Vermont.
Windham
9.8 out of 10, Exceptional, (8 reviews)
"We had such a great stay, the house was perfect for our weekend away and it was so welcoming to the puppies! The host was so great and worked with us when we had to leave early due to the big snowstorm. Would absolutely stay again and highly recommend!"
United States
Jessica M.
Cozy 3 bedroom 2 bathroom chalet centrally located in Southern Vermont.
Terrace/patio

Two Bedroom Chalet, Charming, Quiet, River Front

Two Bedroom Chalet, Charming, Quiet, River Front
Jamaica
9.4 out of 10, Exceptional, (81 reviews)
"We would not recommend staying here in the winter. The house was COLD, we had to wear our ski jackets indoors the first day/evening, it took many hours for the electric baseboard heaters to warm up the bedrooms."
United States
Caroline S.
Two Bedroom Chalet, Charming, Quiet, River Front
Property grounds

Mountain chalet

Mountain chalet
Londonderry
10.0 out of 10, Exceptional, (45 reviews)
"Perfect for our stay and great host!"
United States
Tommy S.
Mountain chalet
Exterior

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
$241 nightly
The price is $244
May 10 - May 11
Total with taxes and fees
Vikings Villages Resort - Double Bed Room
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.
$358 nightly
The price is $404
May 10 - May 11
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
Terrace/patio

Spectacular 4 Season Home on Spruce Lake

Spectacular 4 Season Home on Spruce Lake
Wilmington
9.8 out of 10, Exceptional, (71 reviews)
"The place and location are gorgeous, we absolutely loved it."
United States
Heriberto T.
Spectacular 4 Season Home on Spruce Lake
Property grounds

4-bedroom chalet with outdoor hot tub in lovely Wilmington with WiFi

4-bedroom chalet with outdoor hot tub in lovely Wilmington with WiFi
Wilmington
10.0 out of 10, Exceptional, (5 reviews)
"Amazing home and would love to stay again. "
United States
Evan R.
4-bedroom chalet with outdoor hot tub in lovely Wilmington with WiFi
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

Harvest Barn Inn

Harvest Barn Inn

10/10 Excellent
"Charming B&B. Blessing & Kaelan could not have been nicer, and the breakfast was off the charts!"
Jon 1-night trip
Posted 7 hours ago
Harvest Barn Inn

Find out more about Windham County

Windham County Chalets information

Number of reviews
355
Accommodation
79 Chalets
Lowest Price
$244
Highest Price
$511

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