Top Chalets in Cheshire County in 2026

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

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Top Cities in Cheshire County

A stone archway surrounded by lush greenery and trees.

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

Wilmington

Dawn F.

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!

Wardsboro

Carly L.

HK$3,990 total

includes taxes & fees

9 Nov - 10 Nov

A snow-covered house with a large chimney, surrounded by trees and a snowy landscape.

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

West Dover

"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...

Sandra V.

A cabin with a wooden deck, a red door, and an American flag.

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

Wilmington

Melissa N.

A deck overlooking a lake surrounded by trees.

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

Newbury

Stephanie S.

A wooden deck with wicker furniture, a bench, and a railing overlooking a rocky stream.

6. Two Bedroom Chalet, Charming, Quiet, River Front

Jamaica

Tyler L.

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

Stratton

Karen C.

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.

Windham

Jessica M.

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

Chester

Mark R.

A two-story cabin with a balcony, surrounded by snow and trees.

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

Windham

Brigid M.

A wooden house with a porch lit by string lights, surrounded by snow.

11. Chalet Mount Snow/Stratton Skiing/hiking

East Dover

Roy-michael G.

HK$3,745 total

includes taxes & fees

4 Nov - 5 Nov

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

Wilmington

Evan R.

A laundry room with a washing machine, dryer, and a door leading to another room.

13. Mt Snow Retreat | Walk to brewery

West Dover

"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...

Samira G.

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

Dover

Tim W.

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

West Dover

Michael S.

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

Wilmington

"This beautiful property allowed our entire family to stay together while we did a celebration of life. The communication with owner was absolutely amazing. She was very attentive and enjoy we were good and comfortable during our stay. This beautiful space was so quite peaceful and allowed us all to enjoy eachother with plenty of space. They had everything you would need or possibly forgot their as complimentary. We were all so great to stay and will absolutely return to this beautiful property...

Shelby M.

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

Dover

Brian S.

HK$3,595 total

includes taxes & fees

20 Oct - 21 Oct

A cabin surrounded by autumn foliage and a small pond.

18. Private 6 bedroom Chalet 5min to Mt Snow

Dover

Clifford D.

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.

West Dover

Sarah J.

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

Wilmington

Heriberto T.

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Top Cheshire County Hotel Reviews

Latchis Hotel

10/10 Excellent

"They are right downtown with parking so, unlike other hotels in Brattleboro, guests can walk to local restaurants and attractions in this chrarming river town."

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."

Great Wolf Lodge Boston / Fitchburg, MA

10/10 Excellent

"The facility is great. I was able to get handicapped parking this time which is always a plus. The room was great, very clean. The waterpark was fun. The food was delicious. Specifically at the Fireside restaurant. The staff at the restaurant was fast and efficient. We definitely will be going back."

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent

"It is a charming inn with very lovely staff & family attending the guests. I highly recommend staying here if you appreciate history & charm! The building was built in 1788 I believe they said. We stayed inPikes Suite and were comfortable and happy. Yes, the beautiful old floors creak, but it’s all part of the charm of this lovely still family owned hideaway! I hope to return again!"

The White House Inn

8/10 Good

"It was a beautiful property with friendly staff. The room was very pretty but the mattress was very soft and the pillows were tiny. We loved the fireplace as well but when you lay down you can't see the fire and it was uncomfortable to sit at the end of the bed. A cozy area should be in front of the fire place. However I would still stay there again."

Motel 6 Leominster, MA

10/10 Excellent

"There are few things to be concerned about. You can here your next door neighbor when they speaking loud and there were some cigarettes smoke in the room eventhough we had a non smoking room. It wasn't strong. Overall, the property surprised me how clean it is and how white the sheets and towels are. Very convenient locati I need to shopping area and to the soccer tournament location."

Find out more about Cheshire County

Cheshire County Chalets information

Number of reviews	379
Accommodation	85 Chalets
Lowest Price	HK$3,595
Highest Price	HK$3,990

Chalets in Cheshire County

Change your mind

Treat yourself

Be picky

Check prices for these dates

Top Cities in Cheshire County

West Chesterfield

Our top choices for Cheshire County chalets

1. Beautiful- Ski/Golf home, Hot tub, mins to MTN

2. The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

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

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

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

6. Two Bedroom Chalet, Charming, Quiet, River Front

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

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

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

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

11. Chalet Mount Snow/Stratton Skiing/hiking

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

13. Mt Snow Retreat | Walk to brewery

14. Chalet With A/C, 5 minutes from golf and Mount Snow

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

16. Beautiful Lodging at Mount Snow with Hot Tub on Deck

17. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

18. Private 6 bedroom Chalet 5min to Mt Snow

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

20. Spectacular 4 Season Home on Spruce Lake

Find holiday rentals that suit your style

Top Cheshire County Hotel Reviews

Latchis Hotel

Find out more about Cheshire County

Cheshire County Chalets information

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