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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Chester chalets

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

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
2.0 star property
Plymouth
10.0 out of 10, Exceptional, (14)
"Really enjoyed the setup at the location and the owners were very responsive to any queries!"
United States
Ed N.
The price is AED 658
AED 2,000 total
includes taxes & fees
16 Dec - 17 Dec
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Outdoor spa tub
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

8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
West Dover
10.0 out of 10, Exceptional, (20)
"Had a delightful time here for the Holiday. Quiet place which held us all comfortably! Easy to get to the places we wanted to go to and was well maintained. Communication with the hosts was fantastic."
United States
Jeannine A.
The price is AED 638
AED 2,219 total
includes taxes & fees
15 Dec - 16 Dec
8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
Exterior
Mountain Chalet mins from Mt Snow Skiing/hiking

Mountain Chalet mins from Mt Snow Skiing/hiking

Mountain Chalet mins from Mt Snow Skiing/hiking
East Dover
9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is AED 344
AED 1,492 total
includes taxes & fees
11 Dec - 12 Dec
Mountain Chalet mins from Mt Snow Skiing/hiking
Terrace/patio
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

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.8 out of 10, Exceptional, (22)
"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 AED 341
AED 1,556 total
includes taxes & fees
5 Jan - 6 January 2026
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Terrace/patio
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

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, (14)
"Perfect weekend getaway "
United States
Seth G.
The price is AED 698
AED 1,639 total
includes taxes & fees
11 Dec - 12 Dec
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!

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Wardsboro
10.0 out of 10, Exceptional, (4)
"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 AED 863
AED 2,038 total
includes taxes & fees
14 Dec - 15 Dec
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Exterior
Private cabin: 7 mins to slopes, wood fireplace

Private cabin: 7 mins to slopes, wood fireplace

Private cabin: 7 mins to slopes, wood fireplace
2.0 star property
Dover
9.8 out of 10, Exceptional, (6)
"We spent the week, excellent location and the home was exactly as described in listing."
United States
Chris R.
The price is AED 1,873
AED 3,627 total
includes taxes & fees
15 Dec - 16 Dec
Private cabin: 7 mins to slopes, wood fireplace
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!

Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Dover
10.0 out of 10, Exceptional, (4)
"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 AED 2,020
AED 3,627 total
includes taxes & fees
6 Jan - 7 January 2026
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Exterior
Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres

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)
"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 AED 2,648
AED 4,627 total
includes taxes & fees
7 Jan - 8 January 2026
Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres
Terrace/patio
A Charming Chalet with Hot Tub 1 Mile to Mt. Snow

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, (14)
"Place was super clean. My wife’s favorite video game pac man was down stairs which gave us all a chance to compete against each other and was a blast. We would love to go back A on this property "
United States
Rich H.
The price is AED 1,098
AED 2,615 total
includes taxes & fees
15 Dec - 16 Dec
A Charming Chalet with Hot Tub 1 Mile to Mt. Snow
Smart TV, fireplace, books, stereo
7 min, 10 guests | Stratton Ski Haus | Sauna, HotTub, BootWarmers, 1GB

7 min, 10 guests | Stratton Ski Haus | Sauna, HotTub, BootWarmers, 1GB

7 min, 10 guests | Stratton Ski Haus | Sauna, HotTub, BootWarmers, 1GB
Jamaica
The price is AED 1,240
AED 3,084 total
includes taxes & fees
11 Dec - 12 Dec
7 min, 10 guests | Stratton Ski Haus | Sauna, HotTub, BootWarmers, 1GB
Exterior
NEW Private Chalet - 4 mins to Mt Snow

NEW Private Chalet - 4 mins to Mt Snow

NEW Private Chalet - 4 mins to Mt Snow
Dover
10.0 out of 10, Exceptional, (2)
"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 AED 901
AED 2,446 total
includes taxes & fees
11 Dec - 12 Dec
NEW Private Chalet - 4 mins to Mt Snow
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 Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent
"Nice staff, big room, comfortable bed, walking distance to downtown-overall great stay! "
Amanda 1-night trip
Posted 2 days ago
The Palmer House Resort, an Ascend Collection Hotel