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Chalets in Windham County

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Top Cities in Windham County

A calm lake reflecting a forest with autumn foliage.
ChaletsChalets

Brattleboro

Brattleboro

Our top choices for Windham County chalets

A man standing at a wooden deck door with wicker furniture and string lights.

1. 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, (21 reviews)
"Excellent location and really fun common spaces made this a great choice for our ski vacation. The hosts were super responsive especially when we got a big snow storm and the driveway was plowed. "
United States
Victoria R.
The price is CA $275
CA $816 total
includes taxes & fees
Sep 7 - Sep 8
A Charming Chalet with Hot Tub 1 Mile to Mt. Snow

2. 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
A snow-covered house with a large chimney, surrounded by trees and a snowy landscape.

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

Skybarn Vermont | Pool, 100-Mile Views, Historic Barn
West Dover
10.0 out of 10, Exceptional, (4 reviews)
"Great view!"
United States
Tim V.
Skybarn Vermont | Pool, 100-Mile Views, Historic Barn
A wooden deck with a table and chairs, surrounded by a forest.

4. 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, (9 reviews)
"Loved this place so much! Adorable spot, quaint but has everything you need. Loved the luxury details. "
United States
Carly L.
The price is CA $215
CA $632 total
includes taxes & fees
Sep 15 - Sep 16
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
A cabin with a wooden deck, a red door, and an American flag.

5. Comfy chalet near town, lake, skiing and hiking

Comfy chalet near town, lake, skiing and hiking
Wilmington
10.0 out of 10, Exceptional, (19 reviews)
"Hosts were very responsive and the location was great!"
United States
Melissa N.
Comfy chalet near town, lake, skiing and hiking
A two-story building with balconies, surrounded by trees and a grassy area.

6. 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
A two-story house with a balcony, a chimney, and an American flag.

7. 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, (9 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.
A wooden deck with a table and chairs, a grill, and a small table.

8. 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, (48 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
A wooden deck with wicker furniture, a bench, and a railing overlooking a rocky stream.

9. Two Bedroom Chalet, Charming, Quiet, River Front

Two Bedroom Chalet, Charming, Quiet, River Front
Jamaica
9.4 out of 10, Exceptional, (83 reviews)
"Very cosy and convenient get-away with easy access to Stratton Mountain"
United States
Tyler L.
Two Bedroom Chalet, Charming, Quiet, River Front
A snow-covered balcony with a railing and a view of a forest.

10. Mountain chalet

Mountain chalet
Londonderry
10.0 out of 10, Exceptional, (48 reviews)
"Perfect for our stay and great host!"
United States
Tommy S.
Mountain chalet
A wooden house with a porch lit by string lights, surrounded by snow.

11. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (14 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is CA $162
CA $608 total
includes taxes & fees
Aug 30 - Aug 31
Chalet Mount Snow/Stratton Skiing/hiking
A small, single-story house with a front porch, a red door, and a white fence.

12. The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm

The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm
Wardsboro
10.0 out of 10, Exceptional, (1 review)
"Everything was wonderful and perfect for our family. Super clean and great Vermont experience"
United States
Lisa B.
The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm
A rustic cabin surrounded by autumn foliage, with a clear view of the surrounding forest and a distant mountain range.

13. Modern Lux Cabin w/ Mtn Views | Fire Pit

Modern Lux Cabin w/ Mtn Views | Fire Pit
Stratton
10.0 out of 10, Exceptional, (2 reviews)
"Tommy was a fantastic host!"
United States
Kelsey H.
Modern Lux Cabin w/ Mtn Views | Fire Pit
A two-story building with a staircase leading to the entrance, surrounded by dense greenery and trees.

14. Chalet With A/C, 5 minutes from golf and Mount Snow

Chalet With A/C, 5 minutes from golf and Mount Snow
Dover
10.0 out of 10, Exceptional, (1 review)
"Clean, well maintained and a responsive host."
United States
Tim W.
Chalet With A/C, 5 minutes from golf and Mount Snow
A wooden cabin with an 'OPEN' sign, a wooden deck, and a frozen lake in the background.

15. 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, (48 reviews)
"“Heaven on Earth” provided a true winter haven for our 2 night stay—a peaceful scenic setting for lots of amenities!The children really enjoyed playing in the snow and sled boarding right in the yard and adjacent woods. More fun awaited at the Clubhouse indoor pool and arcade. And cross country skiing was a hit at nearby Prospect Mountain. The hot tub and fireplace enhanced the coziness, and our host was welcoming and responsive. All and all a grand getaway experience!"
United States
Nancy G.
Beautiful Lodging at Mount Snow with Hot Tub on Deck
A two-story wooden house with blue shutters, a front porch with string lights, and two hanging flower baskets.

16. Vermont chalet near beautiful Mount Snow and the quaint town of Wilmington

Vermont chalet near beautiful Mount Snow and the quaint town of Wilmington
West Dover
10.0 out of 10, Exceptional, (26 reviews)
"Great place, close to everything, all amenities and most importantly great hosts!"
United States
Michael S.
Vermont chalet near beautiful Mount Snow and the quaint town of Wilmington
A two-story wooden house with a stone retaining wall, a covered porch, and a small shed.

17. 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
9.4 out of 10, Exceptional, (28 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is CA $170
CA $636 total
includes taxes & fees
Aug 26 - Aug 27
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
A wooden deck with two Adirondack chairs and a small table, overlooking a lake and autumn foliage.

18. 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
A wooden deck with a black Adirondack chair and a small table, surrounded by trees.

19. 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, (20 reviews)
"Cute place, very pet-friendly."
United States
Jeff H.
The price is CA $248
CA $599 total
includes taxes & fees
Sep 1 - Sep 2
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
A cabin surrounded by tall trees with a dirt path leading to it.

20. 10 min from Stratton! Log Cabin w/ Beautiful Views

10 min from Stratton! Log Cabin w/ Beautiful Views
South Londonderry
10.0 out of 10, Exceptional, (14 reviews)
"Always a relaxing stay at the cabin."
United States
Jeffery S.
10 min from Stratton! Log Cabin w/ Beautiful Views
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

Latchis Hotel

Latchis Hotel

8/10 Good
"The room was very clean and the staff was amazing but the proximity of the hotel makes it hard to sleep in the morning. It’s at a very busy intersection, and the train comes through and blasts its horn early in the morning.It is a great place to stay, but if you want to sleep in, it’s not the right place for you."
Michelle 2-night trip
Posted 9 hours ago
Latchis Hotel

Find out more about Windham County

Windham County Chalets information

Number of reviews
472
Accommodation
77 Chalets
Lowest Price
CA $599
Highest Price
CA $816

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