Chalet holiday rentals in Bennington County

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Top-rated chalet rentals in Bennington County

Guests agree: These chalets are highly rated for location, cleanliness and more.

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Guest favourite

Chalet in Dover

4.95 out of 5 average rating, 100 reviews

Wine Moose Hot tub Fireplace Sauna 9min to Mt Snow

My super cozy mountain chalet 10 mins from Mount Snow is the perfect spot to host your Vermont vacation! Let the grownups cozy up by the wood-burning fireplace in the living room, while the kids hang out in the second living room and game room downstairs. With air hockey, shuffleboard, and poker table, they’ll be busy for hours. Hmmm….maybe the grownups will claim that space for themselves! After a long day on the slopes or trails, the sauna, hot tub, or jacuzzi tub will feel great on tired musc

17–24 Oct

$1,004 NZD per night

Guest favourite

Chalet in Stamford

4.92 out of 5 average rating, 62 reviews

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).

8–15 Dec

$480 NZD per night

Guest favourite

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!

29 Jul – 5 Aug

$1,070 NZD per night

Guest favourite

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!

28 Aug – 4 Sep

$458 NZD per night

Guest favourite

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.

11–18 Dec

$295 NZD per night

Superhost

Chalet in Dover

4.84 out of 5 average rating, 202 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

21–28 Oct

$379 NZD per night

Guest favourite

Chalet in Manchester

5.0 out of 5 average rating, 10 reviews

3/3 Chalet on 1 Acre - Manchester (10 mins to VSF)

The Pine Tree Chalet is the quintessential Vermont home with exposed wood interior, a large Great Room perfect for families and friends, and 1 acre of land in a quiet neighborhood. You will feel right at home in this spacious 3 bedroom, 3 bathroom chalet which includes an outdoor fire pit, deck w/ grille, & ping pong table. 5 minutes to outlets / Manchester's dining scene. 10 minutes to summer equestrian (Vermont Summer Festival/HITS) events. 8 minutes to Bromley.22 minutes to Stratton.

13–20 Nov

$735 NZD 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.

13–20 May

$291 NZD 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**

19–26 Jun

$582 NZD per night

Guest favourite

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.

19–26 Dec

$698 NZD per night

Guest favourite

Chalet in Stratton

4.99 out of 5 average rating, 77 reviews

4 acres, Hot Tub, Treehouse, Sauna, Firepit, Grill

HYGGE HOUSE is your private luxury escape on 4 acres of wooded bliss. Perfect for families and small groups of nature-loving adults to make memories in all that the Green Mountains have to offer in any season; hike, mountain bike, kayak, fish, ski, snowshoe, paddle, & golf. Relax in the HOT TUB or SAUNA. Hang out amongst the trees atop the TREEHOUSE. Take a nap in the HAMMOCK. Roast marshmallows by the FIRE PIT. Located 8-12 min to Mt Snow and Stratton Mountain. NO SMOKERS.

26 Oct – 2 Nov

$885 NZD per night

Guest favourite

Chalet in Wilmington

5.0 out of 5 average rating, 60 reviews

Mt Snow Chalet: Peaceful Escape w/Hot Tub

The Mount Snow Chalet is a place to dream a little, play a little and indulge in quintessential Vermont nostalgia. Enjoy some time to disconnect and reconnect with friends & family. Located only 8 miles from Mt Snow Ski Resort & 4 mi from the charming town of Wilmington for dining & shopping. During the summer, enjoy boating and swimming at the Harriman Reservoir or Lake Raponda. No matter what season you choose, fall in love with this special place! Almost Home!

19–26 Nov

$819 NZD per night