
Chalet holiday rentals in Jamaica
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Top-rated chalet rentals in Jamaica
Guests agree: These chalets are highly rated for location, cleanliness and more.

Snug Chalet - Wi-Fi + Close to Mount Snow
This stylish 1971 chalet is a country retreat with modern comforts for you and your family... complete with strong WiFi and a fenced-in dog yard! The minimal cabin is tucked in the trees and set up for families and friends, pet & kid-friendly. 10-15 Minutes to Mount Snow 10-15 Minutes to Downtown Wilmington This is a country house, not a boutique hotel :) If booking during winter or spring months, we HIGHLY recommend a 4wd vehicle as the weather can cause some tough road conditions (snow/mud).

Peaceful VT Chalet w/ Mountain View’s
My peaceful 3-bedroom chalet has everything you need for your VT trip. The house comes with a washer, dryer, Roku TV’s, pullout queen couch. 2.5 bathrooms, indoor elec. fireplace, outdoor fire pit and fully equipped kitchen.Short driving distance to several popular golf courses, shops, restaurants, breweries, fishing, white water rafting, hiking, kayaking, ATV/snowmobile trails, & mountain slopes. An ideal base to explore the Green Moutain National Forests (VT) or the Berkshire Mountains (MA).

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

Pickleball Pool Golf 7min-Stratton DogsOK Fire Pit
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.

Vermont Cabin
Looking for a quick getaway to take in the culture of southern Vermont? Check out this cozy rustic cabin in the woods that comfortably sleeps 2 and is centrally located between skiing, hiking, golfing, camping and unique dining and shops. The cabin is 5 miles from Mount Snow and 5 miles from historic downtown Wilmington, nestled on a quiet private road, but also located just a short walk from the free Moover public transportation Route 7 East Dover Road Stop. Free parking for three vehicles.

Mountain view chalet with hot tub & fire pit!
Welcome to the Vermont View Chalet! 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.

Serene & Stylet Chalet•HOT TUB•Skiing•Manchester
Hey there, relaxation enthusiasts and adventure seekers alike! Shady Pines Chalet is your spot: a groovy 4-bed/2-bath cabin tucked away in the lush, serene embrace of the Green Mountains! It's just 15mins from Manchester, where you can shop and dine like a pro. Plus, you're in prime adventure territory: hiking, kayaking, & fly-fishing are all on the menu. And if you're a winter warrior, Bromley (25min) and Stratton & Magic Mountains (40min) are ready for your skiing prowess!!

Luxe HOT TUB, SAUNA 8–12 min Stratton & Mount Snow
Welcome to HYGGE HOUSE, a luxurious modern retreat on 4 wooded acres in Stratton. Inspired by the Danish concept of hygge, this home embodies warmth, coziness, and well-being. Unwind year-round in a private HOT TUB, SAUNA, and even a TREEHOUSE for the ultimate mountain getaway. Just minutes from Stratton and Mount Snow resorts, this architectural gem is a haven for relaxation and adventure, with an open floor plan, cozy fireplace, and large windows connecting you to nature.
Popular amenities for Jamaica chalet rentals
Family-friendly chalet rentals

Brookside Timber Chalet w/ Hot Tub at Mount Snow

Silver Birch Chalet: Mountain Apt w/ Hot Tub

Lake view chalet 15 min to Mt Snow | 3 min to town

Hilltop Chalet on 20 rolling acres

Peaceful Chalet In Londonderry

New! Mt Snow Chalet w/land, privacy, relaxation

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

Stylish Farmhouse - Close to Ski, Golf + Hot Tub
Luxury chalet rentals

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

The Lodge on Warner Hill

Green Mountain Chalet: Tranquil Oaisis W/Spa

Spacious Chalet W/ Endless Entertainment THE BARN

Hot Tub-1mi To Mt Snow-TheaterRm-Game Room-FirePit

Minutes to Stratton! Large, private home w. sauna

The Great Escape!

Wine Moose Hot tub Fireplace Sauna 9min to Mt Snow
When is the best time to visit Jamaica?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $488 AUD | $509 AUD | $418 AUD | $323 AUD | $323 AUD | $320 AUD | $338 AUD | $338 AUD | $338 AUD | $398 AUD | $338 AUD | $383 AUD |
| 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 holiday rentals
Explore 10 holiday rentals in Jamaica

Nightly prices starting at
Jamaica holiday rentals start at $135 AUD per night before taxes and fees

Verified guest reviews
Over 1,810 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Jamaica holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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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- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Monadnock State Park
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- Pats Peak Ski Area
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- Magic Mountain Ski Resort
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