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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Chester chalets

Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
9.8 out of 10, Exceptional, (10 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is €333
includes taxes & fees
12 Mar - 13 Mar
Chalet Mount Snow/Stratton Skiing/hiking
Terrace/patio

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)
"We had an awesome time here. The property was well stocked with essentials, affordable us some opportunity to unwind, explore the creek, and hang out with the fire pit, board games, and the kids enjoyed the ridge racer arcade. Would absolutely come back!"
United States
Joseph R.
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
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
9.8 out of 10, Exceptional, (24 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 €379
includes taxes & fees
1 Apr - 2 Apr
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Outdoor dining

Private cabin: 7 mins to slopes, wood fireplace

Private cabin: 7 mins to slopes, wood fireplace
Dover
9.8 out of 10, Exceptional, (6 reviews)
"The host - Excellent communication and very accommodating!"
United States
Erika O.
The price is €475
includes taxes & fees
1 Apr - 2 Apr
Private cabin: 7 mins to slopes, wood fireplace
Exterior

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 €453
includes taxes & fees
7 Apr - 8 Apr
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Exterior

Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Dover
10.0 out of 10, Exceptional, (7 reviews)
"We had a great time at the Chalet. Great accommodations Jennifer made sure we had everything we needed She went above and beyond to accommodate our group. "
United States
Chris I.
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Outdoor spa tub

Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus

Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus
Dover
10.0 out of 10, Exceptional, (12 reviews)
"Doug was very communicative and the home was beautiful!"
United States
Kate M.
Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus
Exterior

Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres

Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres
Stratton
10.0 out of 10, Exceptional, (6 reviews)
"We had an amazing stay. It was the perfect location for 4 couples. The owners were super responsive. Amenities were great (our only kitchen recommendation is a non-glass cutting board and individual salt and pepper shakers). Would love to stay again in the summer next time! "
United States
Nicholas D.
Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres
Exterior

Spacious Chalet Near Stratton and Mt. Snow w/Indoor Hot Tub, Fireplace, Firepit

Spacious Chalet Near Stratton and Mt. Snow w/Indoor Hot Tub, Fireplace, Firepit
Wardsboro
10.0 out of 10, Exceptional, (3 reviews)
"Everything was great!"
United States
emilie d.
The price is €934
includes taxes & fees
18 Mar - 19 Mar
Spacious Chalet Near Stratton and Mt. Snow w/Indoor Hot Tub, Fireplace, Firepit
Exterior

NEW Private Chalet - 4 mins to Mt Snow

NEW Private Chalet - 4 mins to Mt Snow
Dover
10.0 out of 10, Exceptional, (3 reviews)
"Mary and Adam were absolutely lovely hosts! From the initial booking to check-in and throughout our stay, they were incredibly responsive. The house was fantastic—completely updated, with a fully equipped kitchen, spacious bedrooms, and a beautiful living area with a cozy fireplace.Our only regret is that we couldn’t stay longer. Thank you, Mary and Adam, for a wonderful stay!"
United States
Patricia N.
The price is €565
includes taxes & fees
23 Mar - 24 Mar
NEW Private Chalet - 4 mins to Mt Snow
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, (16 reviews)
"This place was absolutely amazing! The pictures didn’t do this place justice. The ambience of the deck at night was magical. "
United States
Kaymari T.
The price is €727
includes taxes & fees
1 Apr - 2 Apr
A Charming Chalet with Hot Tub 1 Mile to Mt. Snow
Exterior

New Stratton Ski Haus: A-Frame Hot Tub Sauna EV Privacy 1Gbps Manchester Okemo

New Stratton Ski Haus: A-Frame Hot Tub Sauna EV Privacy 1Gbps Manchester Okemo
Jamaica
10.0 out of 10, Exceptional, (3 reviews)
"Couldn't be better! Outstanding! We had our family holiday ski trip from Dec 25-29th,2025. The amenities were second to none. The hot tub, sauna and fire pit made the winter warm! The house was clean comfortable and very cozy. The kitchen was extremely well appointed (sharp knives!). The staples available (coffee, tea, oil, spices etc.) were high quality and the best I've ever experienced in a short term rental. The beds and bedding were very comfortable! Most immortality the hosts were very...
United States
Laird N.
New Stratton Ski Haus: A-Frame Hot Tub Sauna EV Privacy 1Gbps Manchester Okemo
Exterior

Ski Haus @ Quartermile 3 mins from Base / shuttle King Beds with Private Baths

Ski Haus @ Quartermile 3 mins from Base / shuttle King Beds with Private Baths
Winhall
9.8 out of 10, Exceptional, (17 reviews)
"The place was perfect for our large family!"
United States
Gary N.
The price is €835
includes taxes & fees
1 Apr - 2 Apr
Ski Haus @ Quartermile 3 mins from Base / shuttle King Beds with Private Baths
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 Chester Hotel Reviews

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

6/10 Okay
"Hot tub nor sauna we’re working. This is pretty important for a ski Hotel, or anyone that bills themselves as a spa. "
Karyne 1-night trip
Posted 6 hours ago
The Equinox Golf Resort & Spa

Find out more about Chester

Chester Chalets information

Number of reviews
98
Accommodation
102 Chalets
Lowest Price
€333
Highest Price
€934