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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Chester chalets

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 NZ$684
includes taxes & fees
3 Mar - 4 Mar
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
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 NZ$1,102
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, (23 reviews)
"Wonderful time..the home was very spacious and comfortable..great location!"
United States
Ellen P.
The price is NZ$1,246
includes taxes & fees
10 Feb - 11 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 NZ$828
includes taxes & fees
2 Mar - 3 Mar
Chalet Mount Snow/Stratton Skiing/hiking
Exterior

Chalet-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK

Chalet-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
Jamaica
7.0 out of 10, Good, (2 reviews)
"Its a cabin. Very fun for a group of friends. I wouldnt bring a family here. No running water in the morning"
United States
Hugo T.
The price is NZ$449
includes taxes & fees
12 Feb - 13 Feb
Chalet-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
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 NZ$771
includes taxes & fees
2 Mar - 3 Mar
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 NZ$942
includes taxes & fees
2 Mar - 3 Mar
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
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)
"We spent the week, excellent location and the home was exactly as described in listing."
United States
Chris R.
The price is NZ$1,342
includes taxes & fees
2 Mar - 3 Mar
Private cabin: 7 mins to slopes, wood fireplace
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 NZ$7,840
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 NZ$1,266
includes taxes & fees
10 Mar - 11 Mar
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 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 NZ$1,091
includes taxes & fees
9 Feb - 10 Feb
NEW Private Chalet - 4 mins to Mt Snow
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.
The price is NZ$986
includes taxes & fees
8 Feb - 9 Feb
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
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 didn’t do this place justice. The ambience of the deck at night was magical. "
United States
Kaymari T.
The price is NZ$1,585
includes taxes & fees
9 Feb - 10 Feb
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 NZ$1,732
includes taxes & fees
3 Mar - 4 Mar
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, (2 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.
The price is NZ$1,984
includes taxes & fees
3 Mar - 4 Mar
Stratton A-Frame: Hot Tub Sauna EV Boot Warmers 1 Gbps Manchester Okemo 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

On The River Inn

On The River Inn

10/10 Excellent
"Everything from the manager to the staff to the room and food. 5 stars"
Debra 1-night trip
Posted 2 days ago
On The River Inn

Find out more about Chester

Chester Chalets information

Number of reviews
130
Accommodation
102 Chalets
Lowest Price
NZ$449
Highest Price
NZ$7,840

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