Chalet vacation rentals in Rutland County

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Top-rated chalet rentals in Rutland County

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

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Guest favorite

A private hot tub is illuminated with soft blue lights, creating a relaxing atmosphere. The hot tub features multiple jets and is surrounded by wooden walls and a partially covered area, ensuring privacy. Warm ambient lighting enhances the tranquil setting, inviting relaxation.

Chalet in Killington

4.84 out of 5 average rating, 264 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

The Killington Chalet is your ideal vacation rental in the Green Mountains. It's the Right side of a duplex, perfect for families, couples, and groups. Located just off Killington Rd, it offers a secluded retreat near slopes, restaurants, and outdoor activities. Enjoy skiing, boarding, mountain biking, and more. Features include hot tub, sauna, boot dryer, wood stove, fire pit, and a fully equipped kitchen. Fresh linens, towels, and toiletries provided. Book for a memorable stay in every season!

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Top guest favorite

Chalet in Wells

4.91 out of 5 average rating, 159 reviews

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

June-August '26 special: 2 well-behaved pets stay for the rate of one - S'mores on us! Scenic, nearby lake, golf, hiking! Base rate includes up to 6 guests. Authentic Chalet is private, 3600 sqft, 18 acres, sleeps 13: 3 bedrooms, 1 King, 2 Queen, 3 Twin, 2 Queen sleeper-sofas, 3 full baths. Artisan fireplace, HVAC, oven, Induction cooktop, air fryer, ROKU HDTV, fast Wi-Fi, Fire Pit Patio. Linens/bath towels, soaps supplied. Add on: 5-star private studio/office. Events: reunions & weddings.

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Guest favorite

The exterior of a large chalet is showcased, featuring a steeply pitched roof and expansive windows. A wraparound deck provides access to the outdoors, surrounded by lush greenery. The structure exhibits a dark wood finish that contrasts with the clear blue sky.

Chalet in Granville

4.81 out of 5 average rating, 104 reviews

Hilltop Chalet | 360° Views · Theater · Gym · 6BR

Perched on a private hilltop on the NY/VT border with 360° views of rolling meadows. Sunsets and starry nights are spectacular. Soaring vaulted great room with catwalk, marble kitchen, master suite with jacuzzi, custom castle bunk beds, theater, game room (arcade, basketball, foosball), gym, central AC and fiber (250 Mbps). Outside enjoy a fire pit, bocce ball, and cornhole. Grocery store 5 minutes away. Lake George, Saratoga, Manchester VT and Killington all under an hour. 4WD req. in winter

ValueLocationHeating

Guest favorite

A spacious wooden deck is featured, equipped with a large patio table and six chairs. A hot tub is positioned nearby, surrounded by trees. Large sliding doors offer access to the interior, allowing natural light to fill the space.

Chalet in Killington

4.89 out of 5 average rating, 180 reviews

Kingsbrook: Chalet w Sauna, Hot Tub, AC!

Located off East Mountain Road, on a secluded dead end street, just minutes from your choice of the Killington base lodges. There is access to a ski/hiking trail at the end of our street (1/2 mile from the house), and we're surrounded by hiking and biking trails. The house is great for large groups and families, as there are 2 separate living areas (kids like to hang out in the lower family room with large screen TV and games). Very strong and fast internet. Now with AC for summer getaways!

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Guest favorite

Chalet in Stockbridge

4.92 out of 5 average rating, 50 reviews

Private Mountain Sanctuary | 15 Min to Killington

This is not just a house. Welcome to your one-of-a-kind off-grid nature adventure! *NO Air conditioning. Most summer nights are cool and breezy, and we do have an industrial sized fan, but no AC due to off-grid solar set up. Wow: * Designer modern chalet on 150+ private acres of Vermont wilderness * Off-grid privacy with hiking trails, stargazing, complete seclusion * World-class mountain biking 5 minutes away. 360-degree panoramic views * Hike, Bike, Explore, Stargaze, Views Views Views!

ValueLocationQuiet

Top guest favorite

The chalet is set against a backdrop of mountains and trees. The property features a large green lawn, and two dogs are seen resting on the grass in the foreground. The warm exterior of the home, complete with a deck, can be seen in the background.

Chalet in Wells

4.98 out of 5 average rating, 123 reviews

Chalet on a Hill w/ Mountain & Lake View, Hot Tub

A beautiful chalet situated between mountains and Lake St Catherine. Whether on the deck or inside the house, you can enjoy the tranquil and serene view of the mountains and the lakes. At over 3000 sq ft, the house offers multiple gathering areas, including separate living room(s), a sociable kitchen, a pool table, and a bar. A perfect home for a retreat. Located less than 10 mins from Lake St Catherine Park and country club and many hiking and mt-biking options for the active guests.

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Guest favorite

A rustic ski chalet is nestled among snow-covered trees, with a sloping driveway leading to the entrance. The building showcases a wooden deck and vibrant blue exterior, surrounded by a serene winter landscape.

Chalet in Ludlow

4.84 out of 5 average rating, 94 reviews

Okemo Chalet + HOT TUB

Located just 5 minutes from Okemo Resort and downtown Ludlow, our cozy newly updated chalet offers stunning mountain views, a relaxing hot tub, and access to skiing, hiking, and the beautiful Lakes Region. With spacious living areas, a fully equipped new kitchen and furniture, and streaming services like Netflix and Amazon, it’s perfect for family or group getaways. Two levels of cozy couches, perfect for relaxing after a day of adventure. Killington Resort just 30 minutes to the north.

ValueFamilyHospitality

Guest favorite

A two-story house is set amidst greenery, featuring a welcoming red door and a balcony with chairs. An American flag decorates the front, while gardening tools and vibrant flowers are arranged along the lower level. A grassy area surrounds the property.

Chalet in Killington

4.92 out of 5 average rating, 204 reviews

Close to Mountain and easy walk to restaurants!

We have full weeks available upon request at a substantial discount. Killington Mtn is 1.4 miles away, so the Sports Park is an easy drive. The area offers skiing, snowboarding, tubing, hiking, biking, kayaking, ATVing, PLUS two excellent golf courses nearby. Restaurants and shops are walking distance. The house is casual and comfortable, located on a quiet dirt road with nice views of the valley from the upstairs and deck. There is a HOT TUB and SAUNA and linens included.

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Top guest favorite

A cozy indoor relaxation area features a large hot tub alongside natural wood paneling. Rattan chairs and lounge chairs surround a geometric-patterned rug. Greenery is present, enhancing the tranquil setting. Natural light enters through the window, creating a warm atmosphere.

Chalet in Killington

4.96 out of 5 average rating, 110 reviews

BearHaus Central AC, HUGE Hot Tub, Awesome FirePit

NEW! BearHaus is a fully renovated 6 bedroom Killington chalet that is conveniently located in the heart of town in a tranquil forest setting. The Chalet is built in the classic Austrian style and lovingly renovated top to bottom with brand new modern amenities. There are two kitchens, a giant table for 16 people, one of the biggest hot tubs in all of Killington, a beautiful wet bar with wine fridge and plenty of room for everyone to spread out or hang out together.

LocationFamilyPets

Guest favorite

A two-story chalet features a striking facade with dark wood framing and cream-colored walls. Snow covers the roof and ground, enhancing the winter ambiance. Yellow window shutters and stacked firewood are visible in front, providing a cozy, rustic touch to the scenic setting.

Chalet in Plymouth

4.95 out of 5 average rating, 129 reviews

Ledges Unit: Skyeship Gondola 2 miles w/ HOT TUB

The Ledges Unit is a recently updated home away from home just 2 miles from Killington’s Skyship Gondola. It is only 15 minutes from Killington’s main base area and 20 minutes to Okemo. The Ledges is a 2 story chalet in a 4 unit building. View sister listings by clicking my Host profile picture below. The 1st floor has a kitchen, living room with a large stone mantel and wood stove, dining room, and full bathroom. The 2nd floor has 4 bedrooms and bathroom.

ValueLocationIndoor spaces

Guest favorite

A warm living space is crafted with wooden paneling and large windows that provide natural light. Comfortable seating includes a leather sofa and patterned armchairs, arranged around a wooden coffee table. Soft lighting is provided by lamps, enhancing the cozy atmosphere.

Chalet in Killington

4.86 out of 5 average rating, 265 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

Short walk (200 yds) to Homestretch ski trail at Killington ski mountain. Trail is weather dependent, from late Dec to mid-March. If the nearby trail is not open, it will not be available. Close to hiking/biking trails, golf, nightlife, rivers and lakes. Large open living space and lots of sleeping space makes our home comfortable for large groups. Driveway holds up to 5 cars. Enjoy relaxing in the hot tub, sauna or spending time by the fire.

ValueFamilyWalkability

Guest favorite

A charming A-frame house is presented, set against a colorful sunset. The property features a spacious wrap-around deck with seating, surrounded by trees and greenery. Windows are framed with dark shutters, and the entrance offers a welcoming appearance.

Chalet in Killington

4.95 out of 5 average rating, 104 reviews

Spacious 5BR Chalet | 2 Min to Mountain

🏡 Classic Vermont A-frame chalet – 5BR, 4BA 🎿 2 min to Killington Resort 🚶‍♂️ Walk to town restaurants & shops 🛁 7-person hot tub – open year-round 🔥 2 cozy living rooms w/ Smart TV 🛏️ Ideal for families & groups 🍽️ Full kitchen, large dining area & open floor plan 🌄 Wrap-around deck with great views Perfect for ski trips, family getaways, or mountain escapes!

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