Chester Chalets

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Check prices for these dates

Next weekend
Nov 14 - Nov 16
In two weeks
Nov 21 - Nov 23
In one month
Dec 5 - Dec 7
In two months
Jan 2 - Jan 4

Chalets in Chester

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

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

2.0 star property
Plymouth
10.0 out of 10, Exceptional, (14)
"Excellent week at a cozy property, convenient to Killington and Okemo. Easy check in and check out; highly responsive and helpful host. Would recommend to those looking for a great VT escape."
United States
Amanda L.
$401 nightly
The price is $449
Nov 12 - Nov 13
Total with taxes and fees
Pet-friendly winter retreat in the woods near Okemo + Killington
Exterior
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.
$382 nightly
The price is $432
Nov 9 - Nov 10
Total with taxes and fees
Mountain Chalet mins from Mt Snow Skiing/hiking
Outdoor spa tub
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

West Dover
10.0 out of 10, Exceptional, (20)
"great space for adults and teenagers. loved the hot tub! "
United States
Jessica M.
$540 nightly
The price is $610
Nov 9 - Nov 10
Total with taxes and fees
Hot Tub, Game Room, Fire Pit, Dog friendly, 8 minutes to Ski Mount Snow
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

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.
$360 nightly
The price is $407
Dec 3 - Dec 4
Total with taxes and fees
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Exterior
Private cabin: 7 mins to slopes, wood fireplace

Private cabin: 7 mins to slopes, wood fireplace

2.0 star property
Dover
9.6 out of 10, Exceptional, (5)
"Had a lovely stay here in mid-August. Despite the rain, played two rounds of golf at the beautiful resorts at Mt. Snow and Stratton. The house is nestled in the woods with a great view of the mountain ski trails. House is very spacious and the kitchen has everything you need! Our only issue was the lack of AC. Our bad luck to pick the most humid weekend of the summer, I guess, bc I know AC is rare in VT but maybe add more ceiling fans? Aside from that, we had a great time. "
United States
Suzanne H.
$496 nightly
The price is $560
Nov 9 - Nov 10
Total with taxes and fees
Private cabin: 7 mins to slopes, wood fireplace
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, (8)
"Get together with old friends. Had an easy time checking in and a great time!"
United States
Erik D.
$597 nightly
The price is $675
Nov 12 - Nov 13
Total with taxes and fees
Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus
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, (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.
$423 nightly
The price is $478
Nov 20 - Nov 21
Total with taxes and fees
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
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, (14)
"Perfect weekend getaway "
United States
Seth G.
$378 nightly
The price is $427
Nov 11 - Nov 12
Total with taxes and fees
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Exterior
Bromley Aframe - King Master Bed, Wood Fireplace

Bromley Aframe - King Master Bed, Wood Fireplace

Peru
9.6 out of 10, Exceptional, (14)
"This house was great for my family's spring vacation. The stream was beautiful and relaxing. "
United States
Loni N.
$396 nightly
The price is $443
Nov 30 - Dec 1
Total with taxes and fees
Bromley Aframe - King Master Bed, Wood Fireplace
Exterior
15 min to Killington & Okemo 4-bedroom Chalet w/ Private Sauna & Hot Tub

15 min to Killington & Okemo 4-bedroom Chalet w/ Private Sauna & Hot Tub

2.0 star property
Plymouth
$697 nightly
The price is $781
Nov 10 - Nov 11
Total with taxes and fees
15 min to Killington & Okemo 4-bedroom Chalet w/ Private Sauna & Hot Tub
Exterior
NEW Private Chalet - 4 mins to Mt Snow

NEW Private Chalet - 4 mins to Mt Snow

Dover
10.0 out of 10, Exceptional, (1)
$514 nightly
The price is $581
Nov 10 - Nov 11
Total with taxes and fees
NEW Private Chalet - 4 mins to Mt Snow
Exterior
Mountain Views. Hot Tub. , 5 Wooded Acres. Private Pond

Mountain Views. Hot Tub. , 5 Wooded Acres. Private Pond

Plymouth
Mountain Views. Hot Tub. , 5 Wooded Acres. Private Pond
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, (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.
$619 nightly
The price is $699
Dec 1 - Dec 2
Total with taxes and fees
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

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.
$614 nightly
The price is $694
Nov 11 - Nov 12
Total with taxes and fees
Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres
Terrace/patio
Charming Chalet w. Hot Tub - 1 mile to Mt. Snow

Charming Chalet w. Hot Tub - 1 mile to Mt. Snow

Dover
10.0 out of 10, Exceptional, (14)
"The Chalet was perfect for my families stay in Vermont. We spent the week hiking, exploring the waterfalls and all the towns. The house had everything we needed after a day of hiking. All the games were great too. The house was very clean and well maintained. Thank you for allowing us to stay at The Chalet!"
United States
John S.
$634 nightly
The price is $716
Nov 10 - Nov 11
Total with taxes and fees
Charming Chalet w. Hot Tub - 1 mile 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

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Nice clean room and friendly staff. I was there off season (early November) so some restaurants weren’t open but there were still plenty of options. "
Andrew 1-night trip
Posted 2 days ago
Pointe at Castle Hill Resort

Find out more about Chester

Chester Chalets information

Number of reviews
126
Accommodation
112 Chalets
Lowest Price
$407
Highest Price
$716

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