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Chalets in Cheshire County

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Top Cities in Cheshire County

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ChaletsChalets

West Chesterfield

West Chesterfield

Our top choices for Cheshire County chalets

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, (46 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
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

Modern Chalet Near Mt. Sunapee & Lake Massasecum

Modern Chalet Near Mt. Sunapee & Lake Massasecum
Bradford
10.0 out of 10, Exceptional, (13 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
Exterior

Comfy chalet near town, lake, skiing and hiking

Comfy chalet near town, lake, skiing and hiking
Wilmington
10.0 out of 10, Exceptional, (18 reviews)
"Hosts were very responsive and the location was great!"
United States
Melissa N.
Comfy chalet near town, lake, skiing and hiking
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (12 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is AED 287
AED 1,440 total
includes taxes & fees
14 Jul - 15 Jul
Chalet Mount Snow/Stratton Skiing/hiking
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

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.
Outdoor dining

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 AED 771
AED 1,947 total
includes taxes & fees
21 Jul - 22 Jul
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Exterior

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
Exterior

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
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, (27 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is AED 393
AED 1,623 total
includes taxes & fees
14 Jul - 15 Jul
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
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)
"Perfect place for a quick getaway! Lovely house in a great location!"
United States
Johnna P.
Direct Waterfront, Year-Round, A-Frame Cabin
Outdoor dining

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, (46 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

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

Skybarn Vermont | Pool, 100-Mile Views, Historic Barn
West Dover
10.0 out of 10, Exceptional, (3 reviews)
"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
Terrace/patio

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, (20 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.
A Charming Chalet with Hot Tub 1 Mile to Mt. Snow
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)
"Return customers, love it"
United States
Clifford D.
Private 6 bedroom Chalet 5min to Mt Snow
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, (9 reviews)
"Place was very cozy, and the hot tub was a hit! Exactly as described for a college guys reunion snowboard trip!"
United States
Matt K.
HotTub&GameRm&Traeger Smoker-15 min 2 Mt Snow, Across from Golf, 5 min to Lake
Property grounds

Mountain chalet

Mountain chalet
Londonderry
10.0 out of 10, Exceptional, (46 reviews)
"Perfect for our stay and great host!"
United States
Tommy S.
Mountain chalet
Terrace/patio

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
Exterior

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is AED 1,010
AED 1,254 total
includes taxes & fees
14 Jul - 15 Jul
Vikings Villages Resort - Double Bed Room
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

Newport Motel

Newport Motel

10/10 Excellent
"The older gentleman in the office was so sweet. The king size room is beautiful and the bed is super comfy. I stayed 2 nights for a wedding and it was the best motel for a great price. <3"
Dina 2-night trip
Posted 8 hours ago
Newport Motel