Chalet vacation rentals in Rutland County

A spacious living area is furnished with several dark blue sofas featuring decorative pillows. A central coffee table holds magazines, while a wood stove adds warmth to the space. Natural light streams in through large windows, illuminating the inviting room.

4.84 out of 5 average rating, 251 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!

4.9 out of 5 average rating, 143 reviews

A spacious wooden deck features a smooth surface, bordered by a sturdy railing. Two lounge-style chairs and a circular table are positioned for relaxation. Sunlight casts gentle shadows across the deck, surrounded by lush greenery that offers a serene atmosphere.

Chalet in Wells

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

Base rate includes 6 guests. We welcome events reunions, weddings and film studios! Nearby lake, golf, hiking! Your Private 3600 sq ft home+18 acres has an awesome view! Authentic Chalet sleeps 12 (three bedrooms and baths, two queen sofas, daybed). Summer HVAC, Artisan fireplace, oven, Induction cooktop, stocked kitchen, ROKU HDTV, fast Wi-Fi, FirePit Patio. We supply linens / bath towels for beds and baths. As an option, a Private separate 350 sq ft studio office—5-star by work-from-homers.

4.98 out of 5 average rating, 99 reviews

Chalet in Wells

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

A beautiful chalet situated between the 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 minutes from Lake St Catherine Park and country club and many hiking and mt-biking options for the active guests.

4.92 out of 5 average rating, 181 reviews

A private outdoor jacuzzi is presented on a wooden deck. The jacuzzi features multiple seats and a lightly bubbling surface, inviting relaxation. Surrounding elements include a wall and utility hooks in the background, creating a secluded atmosphere.

Chalet in Stockbridge

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

4.99 out of 5 average rating, 70 reviews

The Overlook - AC | Hot Tub | View | Fires | Games

Escape to stunning mountain views at The Overlook with AC. Just 5 min from Killington Resort, restaurants, and shops. Enjoy the peacefulness of this private cozy mountain chalet after a long day of adventure and unwind in the hot tub, game room, or by the fireplace. Convenient Level 2 EV charger compatible with all EVs at the chalet. 🏔️ Mountain View 🌄 Large decks and balcony 🏖️ Hot tub ⚽️ Game room 🍗 Propane grill 🍳 Fully stocked kitchen 🪵 Fire pit 🔥 Fire table ⚡️Level 2 EV Charger

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.

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!

4.96 out of 5 average rating, 109 reviews

4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!

KILLINGTIME CABIN blends privacy with proximity!! Our 2,600 sq ft chalet is PERFECT for groups traveling with friends & family, with plenty of space for all. 4BR/3BA, large common areas, fieldstone fireplace, spacious kitchen, private deck, Weber grill, and finished walkout lower level with billiards, ski boot dryer, sauna, and hot tub for the ULTIMATE in après-ski luxury. Fast 200MB WiFi and 125+ channel cable TV. Bluetooth sound systems on both levels. Have a BLAST with your loved ones!!

4.95 out of 5 average rating, 118 reviews

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

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.

4.96 out of 5 average rating, 26 reviews

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

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

The living room offers ample seating with a large arrangement of light-colored sofas surrounding a central wooden coffee table. Natural light floods the space through large windows, complemented by a warm wooden floor and soft area rugs. Decorative pillows add subtle touches of comfort.

Chalet in Mount Holly

4.91 out of 5 average rating, 32 reviews

Cozy Chalet near Okemo Jacuzzi/ SAUNA

Contemporary ski chalet minutes from Okemo. Small living room has super comfy seating for 6-8 people and a 55” tv above the gas fireplace . Dining area sits 8. Newly remodeled kitchen w/electric range, dishwasher, coffee makers 30” refrigerator 1st floor Bedroom# 1 king bed. Bathroom w / shower 2nd floor -bedroom #2 king size bed and 45” TV -Full bathroom shared with bedroom next to it Bath has 60” jet tub. -Bedroom #3 . Full size bed 3rd floor 3 twin beds, TV, queen blow up bed

5 out of 5 average rating, 48 reviews

Chalet in Mendon

Luxury Chalet - Hidden Speakeasy- Near Killington

Luxury Ski Chalet in a GREAT location 🚴‍♂️ 15 MINUTES to Killington🏌️‍♂️ 🛀🏼 BRAND NEW HOT TUB 🥃 SECRET BOOKCASE DOOR Hiding a large, well-equipped SPEAKEASY. 🥾 Close to the best HIKING 👰‍♀️ LESS THAN 20 MINUTES to Mountain Top Resort Wedding Venue 🌲 Massive themed KIDS ROOM 🌱 2 MASTER BEDROOMS 🎱 THOUGHTFUL AMENITIES for large families seeking luxury and fun 🔋EV CHARGER 🛌 INCREDIBLY COMFORTABLE beds and linens 🚗 CONVENIENT YET REMOTE 🍁 5 minutes to PICO 🔥 FIRE PIT