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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Chester chalets

Exterior

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 really sweet stay here. It was cozy and comfortable, and had everything as advertised. Plenty of towels and kitchen supplies when we needed them, and the beds were comfortable. We had a great trip to Okemo!"
United States
Carla C.
The price is AEDĀ 959
AEDĀ 1,933 total
includes taxes & fees
27 Jan - 28 Jan
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Exterior

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Plymouth
10.0 out of 10, Exceptional, (14 reviews)
"We had a great stay! Beautiful spot tucked in the woods. Great host communication!"
United States
Julie-Anne B.
The price is AEDĀ 1,102
AEDĀ 2,588 total
includes taxes & fees
9 Feb - 10 Feb
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Exterior

8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly

8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
West Dover
10.0 out of 10, Exceptional, (21 reviews)
"Whole hearted recommend this property for anyone looking to stay in the area. Great location, great atmosphere and most importantly great house. 10/10 hidden gem. "
United States
Joshua L.
The price is AEDĀ 2,432
AEDĀ 4,495 total
includes taxes & fees
18 Feb - 19 Feb
8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
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 AEDĀ 726
AEDĀ 1,969 total
includes taxes & fees
29 Jan - 30 Jan
Chalet Mount Snow/Stratton Skiing/hiking
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, (22 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 AEDĀ 547
AEDĀ 1,781 total
includes taxes & fees
10 Feb - 11 Feb
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
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, (6 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.
The price is AEDĀ 878
AEDĀ 2,171 total
includes taxes & fees
26 Jan - 27 Jan
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
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, (16 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.
The price is AEDĀ 661
AEDĀ 1,590 total
includes taxes & fees
27 Jan - 28 Jan
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
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, (5 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 AEDĀ 698
AEDĀ 1,822 total
includes taxes & fees
27 Jan - 28 Jan
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Property grounds

Green Mountain Manor - Ski and Summer Chalet

Green Mountain Manor - Ski and Summer Chalet
Winhall
9.8 out of 10, Exceptional, (7 reviews)
"Beautiful property less than 5 minutes from Stratton!! Very private and secluded"
United States
Jay T.
The price is AEDĀ 13,094
AEDĀ 18,557 total
includes taxes & fees
21 Feb - 22 Feb
Green Mountain Manor - Ski and Summer Chalet
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, (5 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.
The price is AEDĀ 1,227
AEDĀ 2,706 total
includes taxes & fees
27 Jan - 28 Jan
Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres
Exterior

NEW Private Chalet - 4 mins to Mt Snow

NEW Private Chalet - 4 mins to Mt Snow
Dover
10.0 out of 10, Exceptional, (2 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 fantasticā€”completely updated, with a fully equipped kitchen, spacious bedrooms, and a beautiful living area with a cozy fireplace.Our only regret is that we couldnā€™t stay longer. Thank you, Mary and Adam, for a wonderful stay!"
United States
Patricia N.
The price is AEDĀ 901
AEDĀ 2,412 total
includes taxes & fees
2 Feb - 3 Feb
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, (15 reviews)
"This place was absolutely amazing! The pictures didnā€™t do this place justice. The ambience of the deck at night was magical. "
United States
Kaymari T.
The price is AEDĀ 1,833
AEDĀ 3,598 total
includes taxes & fees
27 Jan - 28 Jan
A Charming Chalet with Hot Tub 1 Mile to Mt. Snow
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, (10 reviews)
"Helpful, fun and warm. "
United States
Anthony S.
The price is AEDĀ 1,468
AEDĀ 3,510 total
includes taxes & fees
26 Jan - 27 Jan
Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus
Exterior

Stratton A-Frame: Hot Tub Sauna EV Boot Warmers 1 Gbps Manchester Okemo MT Snow

Stratton A-Frame: Hot Tub Sauna EV Boot Warmers 1 Gbps Manchester Okemo MT Snow
Jamaica
10.0 out of 10, Exceptional, (1 review)
"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.
The price is AEDĀ 1,440
AEDĀ 3,429 total
includes taxes & fees
27 Jan - 28 Jan
Stratton A-Frame: Hot Tub Sauna EV Boot Warmers 1 Gbps Manchester Okemo MT Snow
Exterior

Stratton Mountain Getaway: Ski Chalet w/Hot Tub, Fireplace, BBQ & Pond Views

Stratton Mountain Getaway: Ski Chalet w/Hot Tub, Fireplace, BBQ & Pond Views
Winhall
8.8 out of 10, Excellent, (16 reviews)
"The house was nice and clean, kitchen was fully equippedā€¦Comfortably the beds are only for 10 adults and two little kids, not for 16 as advertisedā€¦The Futon and two long chairs are not comfortable for sleepingā€¦"
United States
Arti P.
Stratton Mountain Getaway: Ski Chalet w/Hot Tub, Fireplace, BBQ & Pond Views
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

10/10 Excellent
"We have been staying at the Equinox for over 35 yrs. Love the whole scene and vibe. Love the pool and hot tub. Love the big real wood fireplace. "
Patricia 4-night trip
Posted 5 hours ago
The Equinox Golf Resort & Spa