Chalet vacation rentals in Windham County

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Top-rated chalet rentals in Windham County

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Guest favorite

Chalet in Brookline

5.0 out of 5 average rating, 56 reviews

Cozy Vermont Chalet

Relax and visit with family and friends in our cozy, peaceful and kid friendly home. Enjoy many outdoor activities. Hike the Windmill Hill or Long Trails. Swim in, kayak, canoe or tube down the West River. Stroll, run or bike Grassy Brook, Ellen Ware, or River Roads. Bird watch on Putney Mountain. Enjoy winter and other seasonal sports at Stratton, Mt Snow, Grafton Trails and Outdoor Center, as well as other nearby favorites. End your day around the fire pit telling stories and making s’mores!

Jun 2 – 9

G$24,788 GYD per night

Superhost

Chalet in Jamaica

4.78 out of 5 average rating, 400 reviews

Mountain Chalet ~ 7min to Stratton, Views, Private

This authentic Vermont chalet is 3 miles to Stratton Mountain's Sun Bowl, a 7- minute drive away. Spectacular view of Stratton's ski slopes. Swimming hole at the brook on the property. Dogs welcome, $30 fee per dog. No cats due to allergies. Picnic table, fire pit in front yard & propane BBQ grill. Vinyl record player & records, board games, VHS & videos. Full kitchen. Starlink Satellite Internet/WiFi 20-100 mbps. Heat options: 2 propane wall furnaces, wood stove, pellet stove & space heaters.

Jul 17 – 24

G$28,791 GYD per night

Guest favorite

Chalet in Wilmington

4.96 out of 5 average rating, 108 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!

Jul 23 – 30

G$111,247 GYD per night

Guest favorite

Chalet in Stratton

4.99 out of 5 average rating, 143 reviews

Family Chalet Near Skiing, Hiking, Swimming & Golf

Cozy chalet awaits your stay. This home sits on just under 4 acres. Sit back and 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 June of 2023. Open floor plan w/wood burning fireplace. Main bedroom has queen bed and twin bunks. Finished basement with brand new Queen size bed and twin bunk above. Very kid friendly home! Mins to Stratton Mtn and Mt Snow for skiing & golf!

Aug 20 – 27

G$42,578 GYD per night

Guest favorite

Chalet in Dover

4.93 out of 5 average rating, 265 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.

Sep 18 – 25

G$32,188 GYD per night

Superhost

Chalet in Dover

4.84 out of 5 average rating, 201 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

Sep 2 – 9

G$42,531 GYD per night

Guest favorite

Chalet in Dover

4.99 out of 5 average rating, 86 reviews

Cozy Mountain Chalet mins from Mt Snow

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. Experience nature at this peaceful mountain retreat. 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.

Jun 3 – 10

G$27,862 GYD per night

Superhost

Chalet in Jamaica

4.82 out of 5 average rating, 157 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.

Jan 19 – 26

G$53,735 GYD per night

Guest favorite

Chalet in Wardsboro

5.0 out of 5 average rating, 20 reviews

Brook Haven Retreat - Minutes to Mt Snow/Stratton

Welcome to Brook Haven Retreat! We are situated directly on Wardsboro Brook, just minutes away from the best skiing and riding in the Southern Vermont. Skiing, hiking, biking, fishing and relaxation abound! The property features a private fenced yard and deck to take in all the beauty alongside the brook. The home is fully updated with modern conveniences including three sleeping areas, living room, and a fully stocked kitchen. We love and allow well-behaved furry friends in our home!

May 29 – Jun 5

G$47,430 GYD per night

Superhost

Chalet in Wardsboro

4.87 out of 5 average rating, 123 reviews

Hot Tub/Generator Open Floor Home Mt Snow/Stratton

The Pams Hill Chalet, nestled in the Snow Mountain Farms community, is the perfect getaway during any season. Come in the warmer months to enjoy the great deck area, hot tub, and bonfire area outside. Additionally, enjoy the great hiking trails close-by. The house boasts a great open floor plan on the main floor that includes a propane fireplace. The house also offers a great hangout area in the basement that includes a pool table for those nice relaxing nights. **Stairs**

May 5 – 12

G$41,694 GYD per night

Guest favorite

Chalet in Dover

4.97 out of 5 average rating, 104 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.

Sep 3 – 10

G$74,456 GYD per night

Guest favorite

Chalet in Dover

4.89 out of 5 average rating, 152 reviews

Mount Snow cabin with Jacuzzi.

Entire Alpine style Chalet in Mount Snow with outdoor jacuzzi. 1 mile away from the ski lift. 3 bedrooms and 1 loft ( kids playroom), 2 full baths, brand new kitchen with all appliances. Fireplace, TV ( Netflix ), outside terrace, parking onsite up to 2 vehicles. Supermarket nearby ( 5 mins walk ). 1 dog per stay is allowed as long as he is well trained . Dog fee applies. Dog are not allowed to sleep in the beds . 2 dogs per stay is strictly subject to approval .

Nov 29 – Dec 6

G$80,690 GYD per night