
Chalet vacation rentals in Jamaica
Find and book unique chalets on Airbnb
Top-rated chalet rentals in Jamaica
Guests agree: these chalets are highly rated for location, cleanliness, and more.

7 Min Stratton Mtn/15 Min Mt Snow /Wood Fireplace!
Cozy chalet awaits your stay. This home sits on just under 4 acres. Sit back & enjoy the heated sunroom and stare out at the woods that surround you. You may be lucky enough to spot one of the moose or bear that visit the property. Kitchen remodeled 2023! Open floor plan w/wood burning fireplace. Main bedroom has new King Bed & twin bunks. Finished basement with new Queen size bed & twin bunk above. Kid friendly home! Mins to Stratton Mtn & Mt Snow for skiing & golf! Free Disc golf on property.

Chalet Sonsie: A Sweetwater Stay
Chalet Sonsie is a freshly-renovated waterfront getaway, where you can enjoy breathtaking views of Forest Lake year-round, from every room and all 3 levels of decks! Whether you're traveling with the kids, friends, or just looking for a quiet fishing retreat, there's something here for everyone. This cozy 2-bedroom home features 2 full kitchens, 1.5 baths, expansive fireplace and TV, plus a game room complete with foosball and mini-arcade! Book today, or check out other Sweetwater Stays! -Patti

7min-Stratton Dogs OK Fire Pit EV Charger Arboreal
7min drive to pickleball, tennis, pool, golf, mountain biking and skiing @Stratton Resort. Soak up 13 acres of arboreal views from your private chalet. Light-filled w/ southern exposure. Deck and fire pit for stargazing, mid-century modern furnishings, new appliances, and 300Mbps Wi-Fi and a Mini Split AC/Heat. Convenient to ski areas, restaurants, shops, and swimming holes, yet secluded and quiet. Walk to Pikes Falls 29min to Bromley and Mt Snow AWD required for spring/winter. Pet fee $187.

10 min from Stratton! Log Cabin w/ Beautiful Views
Spectacular views of Stratton Mountain! This cozy log cabin is set on 10 acres of land offering a quiet year round Vermont getaway. The home offers 3 bedrooms (all with mountain views), 2 baths and comfortably sleeps 7. Located 10-15 minutes from skiing (Stratton, Bromley and Magic), 25 minutes from shopping and dining in Manchester, and ½ mile from Gale Meadows Pond for hiking and water activities in the summer. If you’re looking for the ultimate Vermont experience, you’ve found your spot!

Mountain view chalet with hot tub & fire pit!
Welcome to the @vermontviewchalet! This spacious, family-friendly property is perfect for year-round enjoyment. With the mountain view as your backdrop, come unplug by the fire pit and unwind in the hot tub. Perfectly situated between Manchester (shopping & dining) and Bromley/Stratton (skiing and entertainment). You're also just 2 minutes away from the Appalachian trail for the best hiking and fall foliage Southern Vermont has to offer. Look no further, you've arrived at your destination.

The Mountain A-Frame at Mount Snow
Entire chalet-style A-Frame in Mount Snow with mountain views. Less than 1 mile from the base of Mount Snow and close to all the fun in the Green Mountains: AT access, swimming holes, covered bridges and more! Across the street you can hop on the Moover shuttle that takes you right to the mountain! 2 minute walk to market, coffee shop and local bar. 2 bedrooms + 1 loft, 1 bath, wrap around deck, cooking necessities, Smart TV and WiFi. You can find us on social (tag us!) @themountainaframe

Bromley Aframe - King Master Bed, Wood Fireplace
Classic Aframe home in a private setting but just down the road from Bromley Ski area and downtown Manchester. Primary bedroom has a king bed, fireplace and french doors to backyard. Second bedroom with queen size bed and third lofted bedroom. Full kitchen with Crate and Barrel dishes and drink ware, coffee maker and cookware. Modern bathrooms renovated in 2022. Great place to come with family for a week away. Skiing in winter or hiking in summer, or just relaxing all year round.

Private Brook Chalet: Hot Tub - Fire pit - Ski
The Brook House Vermont is set back in the trees and unbelievably cozy. It's a place to reconnect while listening to the brook. To enjoy big meals, conversations, and games by the fireplace. To bask in the sun or do yoga on the deck, or gaze into dark, starry skies from the hot tub and fire pit at night. There's skiing mins away at Mount Snow, swimming at Harriman Reservoir, as well as hiking, golf, mountain biking, antiquing, breweries, and some of the best food VT has to offer.

Artists Chalet minutes from Stratton Ski Resort
One of a kind hand gem…built by the owner in the heart of the Green Mountains. House boasts spacious high ceilings, maple trim sourced from the property and custom windows that reflect the intention of the land. Pikes Falls is one mile down the road. Minutes to Stratton Mountain and Jamaica State Park. Mountain views from the deck! During the winter season, all wheel drive or 4WD is recommended. Pets are welcome on a case by case basis and may be subject to a Pet Fee

MountSnow 8 Min, HotTub, GameRoom, FirePit, DogsOk
✔ Relax in the Hot Tub under the Pergola & String Lights ✔ Cozy Fire Pit Area with Adirondack Chairs ✔ Fun Game Room with Air Hockey & Connect Four ✔ 4 Bedrooms, 3 Bathrooms ✔ Dog-Friendly (w/ fee) ✔ 8 Minutes to Mount Snow, 30 minutes to Stratton, 60 minutes to Okemo ✔ 20 minutes to Lake Whitingham/Harriman Reservoir for boating & fishing ✔ Fast Wi-Fi for Remote Work & Streaming ✔ High Chair & Pack N' Play Provided ✔ All Linens, Towels, & Soaps Included

Luxe Hot Tub, Sauna 8-12 min Stratton & Mount Snow
Escape to HYGGE HOUSE, a luxurious modern retreat for 8 on four wooded acres in Stratton. Unwind year-in the private HOT TUB and SAUNA or relax in the rustic TREEHOUSE for the ultimate mountain getaway. Just minutes from Stratton Mountain and Mount Snow, this architectural gem is the perfect blend of seclusion and adventure. Features high-speed internet, a gourmet kitchen, and a cozy stone fireplace. Your ultimate cozy & modern mountain getaway awaits.

Barrel Sauna + Hot Tub & Mtn Views
Escape to Stratton Chalet, 5 mins from a pristine swimming pond, featuring a new hot tub and barrel sauna with incredible Stratton mountain views. Recently renovated, Stratton Chalet features a large stone fireplace, outdoor, modern fire-pit area, two outdoor decks, contemporary outdoor furniture, Bose soundbar, and a well-equipped kitchen.
Popular amenities for Jamaica chalet rentals
Family-friendly chalet rentals

Cozy Lakeview Chalet | Near Mount Snow + Downtown

Chalet w/ hot tub min. to Stratton & Mount Snow

Tranquil Brookside Retreat w/Hot Tub

Chalet-7 min to Ski Stratton-Woodstove-View-Dog OK

3BR Chalet | Skiing | Mountains| Golden Triangle

Designer Chalet w/ Mountain Views close to it all

The Great Escape!

Sheldon Hill Chalet | 4BR Home by Mt Snow/Stratton
Luxury chalet rentals

On Shuttle, Sleeps 10, 4 Bathrooms, Full Kitchen

Secluded Retreat on 22 Acres - Ponds, Hot Tub, A/C

The Lodge on Warner Hill

Green Mountain Chalet: Tranquil Ski Oaisis W/Spa

Spacious Chalet W/ Endless Entertainment THE BARN

Stratton A-Frame: Hot Tub Sauna EV Boot Warmers

Minutes to Stratton! Large, private home w. sauna

Maple Pine w/Hot Tub Pool Table 3min to Mount Snow
When is the best time to visit Jamaica?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$67,868 GYD | G$70,791 GYD | G$58,053 GYD | G$44,897 GYD | G$44,897 GYD | G$44,480 GYD | G$46,985 GYD | G$46,985 GYD | G$46,985 GYD | G$55,338 GYD | G$46,985 GYD | G$53,250 GYD |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Quick stats about chalet rentals in Jamaica

Total vacation rentals
Explore 20 vacation rentals in Jamaica

Nightly prices starting at
Jamaica vacation rentals start at G$25,059 GYD per night before taxes and fees

Verified guest reviews
Over 1,900 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Jamaica vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Jamaica rentals

4.9 Average rating
Jamaica stays are highly rated by guests—averaging 4.9 out of 5!
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- Chalet rentals Windham County
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- Chalet rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Killington Resort
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Pats Peak Ski Area
- Monadnock State Park
- Berkshire East Mountain Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- West Mountain Ski Resort
- Mount Snow Ski Resort
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Crotched Mountain Ski and Ride
- Fox Run Golf Club
- Montshire Museum of Science
- Mount Sunapee Resort
- Mount Monadnock
- Dartmouth College
- Massachusetts Museum of Contemporary Art
- Southern Vermont Arts Center




