Chalets in Cheshire County

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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

Our top choices for Cheshire 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 It felt a bit outdated and in some need of renovation.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 HK$1,449
HK$3,869 total
includes taxes & fees
5 May - 6 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
Outdoor spa tub

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 HK$1,368
HK$6,096 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 HK$2,374
HK$3,773 total
includes taxes & fees
5 May - 6 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 HK$922
HK$3,574 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
Property grounds

Direct Waterfront, Year-Round, A-Frame Cabin

Direct Waterfront, Year-Round, A-Frame Cabin
Antrim
10.0 out of 10, Exceptional, (10 reviews)
"The host was very responsive to our questions and the house was perfect for our family of 4 (plus 1 dog). "
United States
Jaclyn H.
Direct Waterfront, Year-Round, A-Frame Cabin
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

3-bedroom chalet next to skiing, hiking, boating and breweries

3-bedroom chalet next to skiing, hiking, boating and breweries
Bradford
10.0 out of 10, Exceptional, (12 reviews)
"The house was great. Plenty of room to spread out and great views from the living room and deck. The fire pit was an added bonus and all the necessary wood, kindling & lighters were all provided. Well appointed kitchen and the house was clean. Would definitely stay again!"
United States
Ben G.
3-bedroom chalet next to skiing, hiking, boating and breweries
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
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cheshire County Hotel Reviews

Motel 6 Leominster, MA

Motel 6 Leominster, MA

8/10 Good
"Clean room and bathroom"
Kether 1-night trip
Posted 2 hours ago
Motel 6 Leominster, MA

Find out more about Cheshire County

Cheshire County Chalets information

Number of reviews
306
Accommodation
86 Chalets
Lowest Price
HK$3,574
Highest Price
HK$6,096

Explore a world of travel with Expedia