Chalets in Windham County

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Check prices for these dates

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

Top Cities in Windham County

ChaletsChalets

Wilmington

Wilmington
Small waterfalls in a woodland stream surrounded by mossy rocks
ChaletsChalets

Putney

Putney

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 It felt a bit outdated and in some need of renovation.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

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

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

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.
The price is AED 680
AED 1,826 total
includes taxes & fees
7 May - 8 May
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

Mt Snow Game Chalet w/ Hot Tub

Mt Snow Game Chalet w/ Hot Tub
Dover
10.0 out of 10, Exceptional, (12 reviews)
"Helpful, fun and warm. "
United States
Anthony S.
The price is AED 569
AED 2,805 total
includes taxes & fees
12 May - 13 May
Mt Snow Game Chalet w/ Hot Tub
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

LUXE Forest Retreat

LUXE Forest Retreat
Chester
The price is AED 1,113
AED 1,765 total
includes taxes & fees
7 May - 8 May
LUXE Forest Retreat
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 perfect for what we needed for our family road trip"
United States
Tracy R.
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.
The price is AED 432
AED 1,676 total
includes taxes & fees
10 May - 11 May
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
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
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.
Exterior

MtSnow/Stratton Chalet w/Hot Tub

MtSnow/Stratton Chalet w/Hot Tub
Wardsboro
10.0 out of 10, Exceptional, (3 reviews)
"Went with a group of friends and we all enjoyed the house. The hot tub, pool table and extra living room made it the perfect spot to hang out at night after a long day of hitting the slopes. Sam was very responsive and this might be the cleanest VRBO I’ve stayed in."
United States
KAITLYN D.
MtSnow/Stratton Chalet w/Hot Tub
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
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)
"Cute place, very pet-friendly."
United States
Jeff H.
The price is AED 496
AED 1,395 total
includes taxes & fees
20 May - 21 May
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"Had a great stay, staff friendly. Breakfast, lots of options - simple but great for our family. Everything we needed, we will be back. "
Hung Shun 2-night trip
Posted 1 day ago
Hampton Inn Brattleboro