Chalets in Cheshire County

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Our top choices for Cheshire County chalets

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 It felt a bit outdated and in some need of renovation.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

Modern Chalet Near Mt. Sunapee & Lake Massasecum

Modern Chalet Near Mt. Sunapee & Lake Massasecum
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.
Modern Chalet Near Mt. Sunapee & Lake Massasecum

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

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

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

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)
"This is a beautiful place. Has everything you need for an enjoyable stay. Watching the firefly show at night from the deck was amazing. "
United States
Christopher V.
Stratton Mountain Escape w Hot Tub|Deck|Projector

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 753
AED 1,918 total
includes taxes & fees
2 Jun - 3 Jun
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

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

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)
"House is much smaller than it appears, owner turned off hot water in the middle of the night, took hours to get back up in the morning. Appliances are old and clog up. Unreasonable fees "
United States
Boris Y.
Beautiful Lodging at Mount Snow with Hot Tub on Deck

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, (27 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 1,638 total
includes taxes & fees
28 May - 29 May
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Direct Waterfront, Year-Round, A-Frame Cabin

Direct Waterfront, Year-Round, A-Frame Cabin
Antrim
10.0 out of 10, Exceptional, (10 reviews)
"Perfect place for a quick getaway! Lovely house in a great location!"
United States
Johnna P.
Direct Waterfront, Year-Round, A-Frame Cabin

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

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

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Chester
10.0 out of 10, Exceptional, (11 reviews)
"We had a great stay. The house had the perfect amenities for our family ski weekend. Hoping we can come again! "
United States
Hilary S.
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain

Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain
Chester
9.4 out of 10, Exceptional, (6 reviews)
"Greay family trip. Comfortable house with great hot tub and fire pit."
United States
Victoria H.
Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain

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

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

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)
"Great spot, close to Wilmington Town and 10 min from Mount Snow. Cozy set up. Matt was a pleasure to deal with."
United States
David G.
Cozy ski chalet - w/ Assoc amenities. 10 mins from Mount Snow

Spacious 5-bedroom chalet with AC and WiFi in charming Chester

Spacious 5-bedroom chalet with AC and WiFi in charming Chester
Chester
10.0 out of 10, Exceptional, (8 reviews)
"Great cabin with lots of room. Secluded on a country road but very close to town. We had a wonderful stay. "
United States
Mark R.
Spacious 5-bedroom chalet with AC and WiFi in charming Chester
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