Jamaica Chalets from CA $123

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Our top choices for Jamaica chalets

A white, single-story cabin with a red door, surrounded by trees.

1. Ski Stratton A-Frame | Sleeps 10, Hot Tub, Sauna

Jamaica

fran g.

CA $1,467 total

includes taxes & fees

Nov 10 - Nov 11

A wooden deck with a black Adirondack chair and a small table, surrounded by trees.

2. Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Wardsboro

Jeff H.

CA $583 total

includes taxes & fees

Nov 9 - Nov 10

A wooden cabin with a front porch, surrounded by a forest.

3. The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

Wardsboro

Carly L.

CA $641 total

includes taxes & fees

Nov 9 - Nov 10

A small, single-story house with a front porch, a red door, and a white fence.

4. The Perfect Vermont Getaway! 3 bedroom, Fireplace, indoor Pool & Mountain Charm

Wardsboro

Lisa B.

CA $648 total

includes taxes & fees

Nov 9 - Nov 10

A wooden house with a porch lit by string lights, surrounded by snow.

5. Chalet Mount Snow/Stratton Skiing/hiking

East Dover

Chelsea G.

CA $533 total

includes taxes & fees

Nov 8 - Nov 9

A spacious living room with a fireplace, blue sofas, a leather armchair, and a ceiling fan.

6. Luxe Chalet - Leaf Peeping, Near Mt Snow and Stratton Mountain w/Hot Tub, Sauna

Stratton

samantha b.

CA $1,033 total

includes taxes & fees

Nov 8 - Nov 9

A two-story wooden house with a stone retaining wall, a covered porch, and a small shed.

7. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Dover

Brian S.

CA $689 total

includes taxes & fees

Nov 30 - Dec 1

A two-story cabin with a deck, large windows, and a hot tub.

8. Chalet 1mi to Mount Snow with cinema and hot tub

Dover

Liz E.

CA $1,050 total

includes taxes & fees

Nov 10 - Nov 11

A two-story wooden house with a porch, surrounded by snow-covered trees.

9. Mountain Chalet, sleeps 8, with hot tub

Peru

Michael B.

CA $998 total

includes taxes & fees

Nov 10 - Nov 11

10. NEW Private Chalet - 4 mins to Mt Snow

Dover

Mark C.

CA $902 total

includes taxes & fees

Nov 9 - Nov 10

A two-story house with a large deck and a covered porch, surrounded by trees and a grassy yard.

11. Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

Dover

Andrew B.

CA $729 total

includes taxes & fees

Nov 9 - Nov 10

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Learn more about Jamaica

Tucked along the West River, this charming village offers hiking trails and swimming holes perfect for summer exploration. Visit Jamaica State Park to discover Hamilton Falls or enjoy winter skiing at nearby Stratton Mountain.

See all hotels in Jamaica

A mountainous landscape with autumn foliage, a river, and a small pond.

Top reviews in Jamaica

A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

Four Columns Inn

Newfane

10/10 Excellent

Marie-Christine

A large building with a symmetrical facade, a central entrance with a glass door, and two smaller structures on either side.

Inn At Mount Snow

West Dover

10/10 Excellent

marco

A rustic lodge with stone walls, a stone fireplace, and outdoor seating.

Seesaw's Lodge

Peru

10/10 Excellent

We enjoyed our stay immensely! Our room was lovely and clean. The pillows and bed were very comfortable! The Green Mountain coffee in our room was a nice touch! Our only complaint was that there wasn’t real cream for our coffee, so next time, we will bring our own. The large walk-in shower was very nice as well. The main common area was beautiful and homey! The kitchen seemed fully equipped, but we didn’t have any meals there. We will definitely come back for a longer stay!

Joy