Chalets in Cheshire County

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Our top choices for Cheshire County chalets

Two Bedroom Chalet, Charming, Quiet, River Front

Two Bedroom Chalet, Charming, Quiet, River Front
Jamaica
9.4 out of 10, Exceptional, (81 reviews)
"This place was just what we need to get away from big-city living for a week."
United States
Scott P.
Two Bedroom Chalet, Charming, Quiet, River Front

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

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 It felt a bit outdated and in some need of renovation.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

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
9.8 out of 10, Exceptional, (17 reviews)
"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.

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)
"Stay was amazing! Location was perfect, the house was in immaculate condition and the host made it super easy. Everything required to enjoy the house was in place; firewood, towels, sheets, kitchenware and even pancake mix!!! Hope to be back…"
United States
Joao R.
Cozy 3 bedroom 2 bathroom chalet centrally located in Southern Vermont.

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 533
AED 1,444 total
includes taxes & fees
19 Apr - 20 Apr
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Comfy chalet near town, lake, skiing and hiking

Comfy chalet near town, lake, skiing and hiking
Wilmington
10.0 out of 10, Exceptional, (16 reviews)
"Nice property. Accurate listing. Clean and good communication. Had a great time."
United States
tom c.
Comfy chalet near town, lake, skiing and hiking

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, (25 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 1,663 total
includes taxes & fees
9 Apr - 10 Apr
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

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, (45 reviews)
"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

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

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)
"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

Wine Moose Hot tub Fireplace Sauna 9min to Mt Snow

Wine Moose Hot tub Fireplace Sauna 9min to Mt Snow
Dover
10.0 out of 10, Exceptional, (8 reviews)
"We had a great time at the Wine Moose! The sauna kept us super warm in the super cold temps. Very very close to Mt. Snow and we also hit up Berkshire East and Magic an hour south and north respectively, easily. I'd recommend staying here!"
United States
Zach F.
Wine Moose Hot tub Fireplace Sauna 9min to Mt Snow

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, (7 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 716
AED 1,851 total
includes taxes & fees
27 Apr - 28 Apr
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

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

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

LUXE Forest Retreat

LUXE Forest Retreat
Chester
The price is AED 1,113
AED 1,773 total
includes taxes & fees
6 Apr - 7 Apr
LUXE Forest Retreat

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

Private cabin: 7 mins to slopes, wood fireplace

Private cabin: 7 mins to slopes, wood fireplace
Dover
9.8 out of 10, Exceptional, (8 reviews)
"The host - Excellent communication and very accommodating!"
United States
Erika O.
The price is AED 474
AED 1,864 total
includes taxes & fees
12 Apr - 13 Apr
Private cabin: 7 mins to slopes, wood fireplace

Cozy ski chalet - w/ Assoc amenities. 10 mins from Mount Snow

Cozy ski chalet - w/ Assoc amenities. 10 mins from Mount Snow
Wilmington
10.0 out of 10, Exceptional, (14 reviews)
"Property had attention to details and was 'plug and play' when it came to enjoying our stay. The house was fully furnished. Fireplace was a bonus especially after a full day of skiing/snowboarding. I would recommend this property to others for anytime of the year. "
United States
Anonymous traveler
Cozy ski chalet - w/ Assoc amenities. 10 mins from Mount Snow

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
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 Cheshire County Hotel Reviews