Chalet holiday rentals in Jamaica

Find and book unique chalets on Airbnb

Top-rated chalet rentals in Jamaica

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Guest favourite

Chalet in Wilmington

4.96 out of 5 average rating, 109 reviews

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).

Top guest favourite

Chalet in Wells

4.9 out of 5 average rating, 143 reviews

Views! Entire Chalet, FAST Wi-Fi, All 18 Acres

We Welcome events fam. reunions, weddings and film studios! Ski most resorts within an hour! You will enjoy the entire 3600 sq ft home+18 acres with an awesome view! True Chalet sleeps 12 and it’s perfect for retreats, family reunions, getaways. AC+radiant heat, Artisan fireplace, oven, Induction cooktop, stocked kitchen, ROKU HDTV fast Wi-Fi. For bed and bath, we supply the linens and bath towels. An optional separate 350 sq. ft. private studio office, 5-star by work-from-homers, is available

Guest favourite

Chalet in Mount Holly

4.97 out of 5 average rating, 151 reviews

Charming Summit View Chalet near Okemo and Lakes

Welcome to Mount Holly! Our chalet is a 3-level, 3-bedroom, 2-full bathroom home slightly northwest of Okemo. A bright, comfortable home with large deck & mountain views. 4 miles to skiing and lakes! 2 Queen beds & a bunk w/full & twin bed - sleeps 7 people max. Large laundry room with full size washer/dryer. Full kitchen. Sits on private, 1-acre wooded lot in quiet wooded neighborhood. Short drive to restaurants, hikes, lakes, cheese shop & local farm. Local helpers in the neighborhood.

Superhost

Chalet in Wilmington

4.79 out of 5 average rating, 188 reviews

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.

Guest favourite

Chalet in Wilmington

4.95 out of 5 average rating, 147 reviews

Mountain View Retreat: 5 Mi to MT Snow, Hot Tub

Come escape to Wilmington, Vermont. Stunning views of Mt. Snow, a small stream, and a large hot tub on 12 secluded acres. Only 10 minutes to Mount Snow and 30 minutes to Stratton our home is the perfect getaway for your VT adventure with all of your family and friends. Come ski, snowboard, snowmobile, hike, kayak, mountain bike, swim, or fish just minutes away! After your long day exploring come relax in the hot tub, by the fire, in the game room, or just out on our deck taking in the sunset!

Guest favourite

Chalet in Dover

4.92 out of 5 average rating, 302 reviews

A charming VT chalet

Charming chalet nestled in the Mt Snow valley. Relax to the sound of a babbling brook in the back yard while you hang around a stone fire pit! Unwind in the quiet serenity of this country home complete with fully equipped kitchen with a newly installed gas fireplace , a comfy open living room with flat screen cable tv & DVD player Roko & High speed Internet . We have a lock box located on the post near the front entrance. combo provided upon arrival . Washer & dryer located on first level.

Superhost

Chalet in Dover

4.86 out of 5 average rating, 256 reviews

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

Guest favourite

Chalet in Jamaica

4.82 out of 5 average rating, 171 reviews

Artists Chalet minutes from Stratton Ski Resort

One of a kind, brand new, hand built by owners in the heart of the Green Mountains. House boasts spacious high ceilings, built with wood from the property and custom windows that reflect the true intention of the h’om’e. Beautiful pikes falls less than one mile down the road. Minutes to Stratton Mountain and Jamaica State Park. Partial mountain view’s! 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.

Top guest favourite

Chalet in Jamaica

4.98 out of 5 average rating, 258 reviews

Vermont Chalet

Escape to our cozy A-frame on 3 private acres in Southern Vermont for a peaceful, secluded retreat. Relax to the soothing sounds of the river across the street while unwinding on the covered, enclosed porch. Enjoy a fully stocked kitchen, updated bathroom, strong WiFi, video games and books by a warm wood stove. Explore local towns, hiking, or wander through our tranquil forest. With an EV charger, local artisan soaps, and warm woodstove, this is the perfect spot for a serene getaway.

Guest favourite

Chalet in Dover

4.94 out of 5 average rating, 121 reviews

Mountain Chalet mins from Mt Snow Skiing/hiking

Experience nature at this peaceful mountain retreat. World class skiing at Mt Snow is just 14 minutes away. After a day of outdoor activities enjoy a relaxing time in front of the fireplace. This cozy chalet boasts exposed wood beams and wood paneling all throughout the house. You will wake up in the master bedroom with views of the woods. During the off winter months, enjoy your morning coffee on patio with views of the mountain. The kitchen is well equipped with your cooking needs.

Top guest favourite

Chalet in Dover

4.97 out of 5 average rating, 113 reviews

Grey Wolf's Den: 5 miles to Mount Snow w/HOT TUB

Charming spacious A-frame with lots of natural light, beautiful scenery and wrap around deck. Property features a long rolling hill perfect for sleigh riding or 75' slip n slide, tennis court, firepit, and 5 acres of Green Mountain Nat'l forest and brook. Home has 3 bedrooms + loft area.. 5 miles to Mount Snow, and minutes to golf course, bars/restaurants and lakes. This house is action packed inside and out with hot tub, 200' zipline and "unlock the box" scavenger hunt.

Guest favourite

Chalet in Stratton

4.96 out of 5 average rating, 131 reviews

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.