Chester Chalets
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Our top choices for Chester chalets
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Cozy 4bd - Ski Okemo, Killington, Magic & BromleyChester
10.0 out of 10, Exceptional, (10)
"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!"
Carla C.
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Pet-friendly winter retreat in the woods with fireplace near Okemo + KillingtonPlymouth
10.0 out of 10, Exceptional, (14)
"Really enjoyed the setup at the location and the owners were very responsive to any queries!"
Ed N.
$517 nightly
The price is $579
Jan 5 - Jan 6, 2026
Total with taxes and fees
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 HouseDover
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. "
SZU YIN C.
$355 nightly
The price is $401
Jan 5 - Jan 6, 2026
Total with taxes and fees
Mountain Chalet mins from Mt Snow Skiing/hiking
Mountain Chalet mins from Mt Snow Skiing/hikingEast Dover
9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
Roy-michael G.
$420 nightly
The price is $475
Jan 5 - Jan 6, 2026
Total with taxes and fees
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."
Kristen T.
$451 nightly
The price is $510
Jan 13 - Jan 14, 2026
Total with taxes and fees
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. "
Chris I.
$524 nightly
The price is $592
Jan 1 - Jan 2, 2026
Total with taxes and fees
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 "
Seth G.
$426 nightly
The price is $481
Jan 20 - Jan 21, 2026
Total with taxes and fees
Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres
Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acresStratton
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! "
Nicholas D.
$655 nightly
The price is $740
Jan 13 - Jan 14, 2026
Total with taxes and fees
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
10/10 Excellent
Find out more about Chester
Chester Chalets information
Number of reviews | 81 |
|---|---|
Accommodation | 102 Chalets |
Lowest Price | $401 |
Highest Price | $970 |
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