Chalet vacation rentals in Rutland County

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Top-rated chalet rentals in Rutland County

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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, 249 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!

Top guest favorite

The chalet features a striking A-frame design with two-story stone columns supporting a spacious deck. Soft lighting accentuates the exterior, while lush greenery surrounds the base. The entryway displays a welcoming atmosphere with a bench and lantern illuminating the path.

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 favorite

The chalet is nestled within a snowy woodland, framed by tall evergreen trees. A snow-covered driveway leads up to the home, showcasing its rustic charm and green roof. The entrance and deck are partially visible, inviting guests to explore the surrounding nature.

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.

Guest favorite

A well-lit outdoor Jacuzzi features soothing water jets, creating a relaxing ambiance. The water is illuminated with soft lights, enhancing the tranquil setting. Visible edges and seating areas allow for comfortable relaxation. Surrounding space remains dark, emphasizing the warm glow of the Jacuzzi.

Chalet in Stockbridge

4.92 out of 5 average rating, 181 reviews

Killington ski house winter MTbike -new jacuzzi

Killington Ski Area with access to snowmobile mountain biking trails. This 3 bedroom, 2 bath upper unit duplex. with outdoor private Jacuzzi open year round with barbecue on very nice decks for those nicer days , snow mobile right from the house , on the tweed valley vast trails , in the summer mountain bike on the green mountain trail system right on our mountain keep us in mind for the summer event like the spartan race and the peak series Mt biking events Fantastic unit check our reviews

Superhost

A pathway of wooden steps leads up to a charming house surrounded by lush greenery. The house features a spacious deck with a gentle curve, inviting outdoor relaxation. A gravel area provides ample parking space, blending seamlessly with the natural landscape.

Chalet in Killington

4.9 out of 5 average rating, 162 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!

Top guest favorite

An inviting outdoor space features a fire pit surrounded by natural stones, with string lights overhead creating a warm glow. The chalet is illuminated from within, showcasing large windows that blend indoor and outdoor environments. A projection screen stands to the left, enhancing the entertaining atmosphere.

Chalet in Mendon

5 out of 5 average rating, 45 reviews

Luxury Chalet Close to Skiing, Golf, and Weddings

Luxury Ski Chalet in a GREAT location ⛷️15 MINUTES to Killington 🛀🏼 Incoming HOT TUB- mid May 2025 🥃SECRET BOOKCASE DOOR Hiding a large, well-equipped SPEAKEASY. 👰‍♀️LESS THAN 20 MINUTES to Mountain Top Resort Wedding Venue 🌲 Massive themed KIDS ROOM 🌱TWO MASTER BEDROOMS with private bathroom access. 🔥 THOUGHTFUL AMENITIES for large families seeking luxury and fun 🔋EV CHARGER 🛌 INCREDIBLY COMFORTABLE beds and linens 🚗 CONVENIENT YET REMOTE ❄️5 MINUTES to the base of Pico 🧼LAUNDRY

Guest favorite

A hot tub is situated under a wooden gazebo, with views of a snow-covered chalet in the background. The exterior features traditional black and white architecture, framed by tall trees. The sky appears bright blue with scattered clouds.

Chalet in Plymouth

4.95 out of 5 average rating, 118 reviews

Ledges Unit:1 mile to F&W Summer Camp w/ HOT TUB

The Ledges Unit at Killington’s Brookside Manor is a freshly renovated home away from home just 2 miles from Killington’s Skyeship 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. 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. The other 3 listings at this location are rented separately.

Guest favorite

A cozy chalet is nestled among tall trees, with a fire pit surrounded by seating. The exterior showcases a mix of wood and green materials, and a balcony extends from the upper level. Sunlight filters through the leaves, creating a serene outdoor setting.

Chalet in Mendon

4.96 out of 5 average rating, 26 reviews

Pico/ Killington chalet, minutes to the mountain

Welcome to our boutique style mountain chalet nestled in tall birch trees. Our fully equipped modern home is 10 mins to Pico and 15 minutes to the Killington access road. Whether you’re in VT to shred the Beast of the East or leaf peep the Green Mountains our home offers a cozy retreat for some time to relax between adventures. Close to breweries, orchards, hiking on the Appalachian Trail/Long Trail, and the convenience of Rutland. AND… We’re walking distance to pancakes and putt-putt =).

Superhost

Chalet in Plymouth

4.75 out of 5 average rating, 215 reviews

5BR Chalet in Historic Town bet Killington & Okemo

“Coolidge Retreat” 5 bedroom secluded Chalet on a 5 acres of hilly forest land with a Hot tub (w/ a separate service fee). Located in Historical Plymouth VT, between both resorts 20 min. in either direction (10 min. to Killington Skyship Gondola). 5 min. to Snowmobile tours, 9 min. to Long Trial Brewery, 2 min. to Plymouth Artesian Cheese factory & Calvin Coolidge Homestead Historic site. Also lots of lakes in the area with swimming, boating, and fishing. Canoe available for a $60 fee.

Superhost

Chalet in Killington

4.71 out of 5 average rating, 24 reviews

On access rd. 3bedr. 2bath. Large 10skiers HOT TUB

Hideaway Chalet has excellent location right on access road, walking to restaurants and bars.Part of Killington sidewalk. Leave your car on our maintained secluded private parking lot and take bus to gondola. You are staying close to it all, and yet secluded in forest setting. This listing is for ground level apartment 3 bedr. 2 bathrooms living room and dry bar. It does not have full kitchen. feel free to ask questions. Hot tub is right by private entrance and has fee based on occupancy.

Guest favorite

A stone pathway is framed by lush greenery and garden beds leading to the entrance of the chalet. Soft lighting from lanterns illuminates the steps, creating a welcoming atmosphere as it transitions from the natural surroundings to the home's entrance.

Chalet in Stockbridge

4.96 out of 5 average rating, 126 reviews

Gnome Home Mountain Ski Chalet w/Sauna Killington

Mountaintop Chalet perched in the heart of Green Mountains. Enjoy true mountain living all year long 25m to Killington, White River access minutes from home, abundance of hiking trails, and golf courses. Central to Killington, Rochester, & Woodstock. After your adventures, return to a welcoming & comfortable home with beautiful views from every room, multiple decks, new! fireplace, & sauna, and plenty of special touches to help you unwind and relax.

Guest favorite

A spacious living area features wood-paneled walls and a high ceiling, adorned with large windows that provide natural light. Comfortable seating options include a sofa and chairs arranged around a central table. A decorative rug enhances the warm ambiance, creating a cozy gathering space.

Chalet in Killington

4.87 out of 5 average rating, 248 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.