A large rock with carved faces and a river in the background.

Chalets in Cheshire County

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Top Cities in Cheshire County

A town nestled among dense forests with a river and a bridge.
ChaletsChalets

Swanzey

Swanzey

Our top choices for Cheshire County chalets

A deck with a table and chairs, a grill, and a view of a grassy field.

1. 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 wooden deck with a table and chairs, surrounded by a forest.

2. 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, (13 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 $264
CA $700 total
includes taxes & fees
Oct 14 - Oct 15
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
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, (6 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
A cabin with a wooden deck, a red door, and an American flag.

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

Comfy chalet near town, lake, skiing and hiking
Wilmington
10.0 out of 10, Exceptional, (20 reviews)
"Hosts were very responsive and the location was great!"
United States
Melissa N.
Comfy chalet near town, lake, skiing and hiking
A deck overlooking a lake surrounded by trees.

5. Waterfront Family Friendly 3bed/2Bath home near Sunapee

Waterfront Family Friendly 3bed/2Bath home near Sunapee
Newbury
10.0 out of 10, Exceptional, (3 reviews)
"Everything was wonderful. We truly enjoyed our stay!"
United States
Stephanie S.
Waterfront Family Friendly 3bed/2Bath home near Sunapee
A wooden deck with wicker furniture, a bench, and a railing overlooking a rocky stream.

6. 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 rustic cabin surrounded by autumn foliage, with a clear view of the surrounding forest and a distant mountain range.

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

Modern Lux Cabin w/ Mtn Views | Fire Pit
Stratton
10.0 out of 10, Exceptional, (3 reviews)
"Great place to stay for many families!"
United States
Karen C.
Modern Lux Cabin w/ Mtn Views | Fire Pit
A two-story house with a balcony, a chimney, and an American flag.

8. Cozy 3 bedroom 2 bathroom chalet centrally located in Southern Vermont.

Cozy 3 bedroom 2 bathroom chalet centrally located in Southern Vermont.
Windham
10.0 out of 10, Exceptional, (12 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 hot tub on a wooden deck with a view of a forest and a lake.

9. 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, (9 reviews)
Spacious 5-bedroom chalet with AC and WiFi in charming Chester
A two-story cabin with a balcony, surrounded by snow and trees.

10. Peaceful chalet near Bromley, Magic, Okemo, Mount Snow, and Stratton

Peaceful chalet near Bromley, Magic, Okemo, Mount Snow, and Stratton
Windham
10.0 out of 10, Exceptional, (5 reviews)
"Great place"
United States
Brigid M.
Peaceful chalet near Bromley, Magic, Okemo, Mount Snow, and Stratton
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, (16 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is CA $208
CA $683 total
includes taxes & fees
Nov 4 - Nov 5
Chalet Mount Snow/Stratton Skiing/hiking
A red house with a porch and a gravel driveway surrounded by trees with autumn leaves.

12. The Davis Hill House - 4BR, Hot Tub, Privacy & 8 Min to Mount Snow

The Davis Hill House - 4BR, Hot Tub, Privacy & 8 Min to Mount Snow
Wilmington
9.8 out of 10, Exceptional, (7 reviews)
"Amazing home and would love to stay again. "
United States
Evan R.
The Davis Hill House - 4BR, Hot Tub, Privacy & 8 Min to Mount Snow
A laundry room with a washing machine, dryer, and a door leading to another room.

13. Mt Snow Retreat | Walk to brewery

Mt Snow Retreat | Walk to brewery
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"The exceeded our expectation. The place is beautiful clean and has every thing that makes the guest comfortable and relaxed. We really enjoyed it. I will give the place 5 We would like to book again God willing when the ski season starts we really enjoyed our stay very much and we appreciate the host’s quick response which was immediately after we contact him for anything, thanks again And and we will book the same place again and we will recommend it for our friends and family Samir and Samira...
United States
Samira G.
Mt Snow Retreat | Walk to brewery
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 two-story wooden house with blue shutters, a front porch with string lights, and two hanging flower baskets.

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

Vermont ski chalet near beautiful Mount Snow and the quaint town of Wilmington
West Dover
10.0 out of 10, Exceptional, (27 reviews)
"Great place, close to everything, all amenities and most importantly great hosts!"
United States
Michael S.
Vermont ski chalet near beautiful Mount Snow and the quaint town of Wilmington
A wooden cabin with an 'OPEN' sign, a wooden deck, and a frozen lake in the background.

16. 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, (49 reviews)
Beautiful Lodging at Mount Snow with Hot Tub on Deck
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, (29 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is CA $182
CA $661 total
includes taxes & fees
Oct 20 - Oct 21
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
A cabin surrounded by autumn foliage and a small pond.

18. Private 6 bedroom Chalet 5min to Mt Snow

Private 6 bedroom Chalet 5min to Mt Snow
Dover
9.8 out of 10, Exceptional, (17 reviews)
"Return customers, love it"
United States
Clifford D.
Private 6 bedroom Chalet 5min to Mt Snow
A two-story house with a garage, surrounded by snow-covered trees and a clear sky.

19. COZY TREE LIKE HOUSE. WALK TO MARKET & REST. LOW RATES. 1 MILE TO MT SNOW.

COZY TREE LIKE HOUSE. WALK TO MARKET & REST. LOW RATES. 1 MILE TO MT SNOW.
West Dover
9.8 out of 10, Exceptional, (39 reviews)
"The view was beautiful and the living room was very spacious and had plenty of room for our group to hang out and spend time together. "
United States
Sarah J.
COZY TREE LIKE HOUSE. WALK TO MARKET & REST. LOW RATES. 1 MILE TO MT SNOW.
A wooden deck with two Adirondack chairs and a small table, overlooking a lake and autumn foliage.

20. Spectacular 4 Season Home on Spruce Lake

Spectacular 4 Season Home on Spruce Lake
Wilmington
9.8 out of 10, Exceptional, (72 reviews)
"The place and location are gorgeous, we absolutely loved it."
United States
Heriberto T.
Spectacular 4 Season Home on Spruce 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

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"My sister and I needed a very last minute place to stay after our VRBO rental was not what we thought. The ladies at the front desk were really nice and very help. The beds and pillows were very comfortable and the room was very clean. The only issue is the area, it’s a bit of a drive if you want to shop however, one minute up the road is Murdoch’s restaurant and they had delicious food. We ate there twice. Just make sure to make a reservation. All in all it was a nice stay and we definitely suggest staying there."
Stephanie 1-night trip
Posted less than an hour ago
Pointe at Castle Hill Resort

Find out more about Cheshire County

Cheshire County Chalets information

Number of reviews
379
Accommodation
88 Chalets
Lowest Price
CA $661
Highest Price
CA $700

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