Chalet holiday rentals in Wilmington

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Top-rated chalet rentals in Wilmington

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Guest favourite

Chalet in Cummington

4.86 out of 5 average rating, 101 reviews

Berkshire A-Frame Chalet!

Our secluded home is just off of route 9 in Cummington. We are less than 1 hour away from many attractions including Tanglewood, Mass MoCA, Glendale Falls and Northampton. This area is not only beautiful for hiking, but also motorcycle riding here is exquisite! No wifi or cable (plenty of movies!), good cell phone coverage for Verizon and AT&T (tMobile has not worked in the past, but recently guests have said that it does work). Friendly pets welcome! 1 pet maximum. We abut Shire Village Camp.

6–13 Jul

$236 SGD 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!

23–30 Jul

$722 SGD 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!

20–27 Aug

$278 SGD 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.

18–25 Sep

$210 SGD 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

2–9 Sep

$278 SGD per night

Guest favourite

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.

3–10 Jun

$184 SGD 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.

19–26 Jan

$350 SGD 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**

5–12 May

$272 SGD 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.

3–10 Sep

$486 SGD per night

Guest favourite

Chalet in Wilmington

5.0 out of 5 average rating, 59 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!

8–15 Dec

$554 SGD per night

Guest favourite

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 .

29 Nov – 6 Dec

$526 SGD per night

Guest favourite

Chalet in Wells

4.89 out of 5 average rating, 133 reviews

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

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, creatives. HVAC Heat/AC+baseboards. 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

9–16 Mar

$473 SGD per night