Chalet holiday rentals in Rutland County

Find and book unique chalets on Airbnb

Top-rated chalet rentals in Rutland County

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Chalet in Killington

5.0 out of 5 average rating, 39 reviews

The Overlook | Hot Tub | Game Room | Mountain View

Escape to stunning mountain views at The Overlook. 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. Take advantage of the 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

Chalet in Stockbridge

4.93 out of 5 average rating, 168 reviews

Killington spring ski - MTbike -new jacuzzi

Killington Ski Area with access to snowmobile and mountain biking trails. This is a 3 bedroom, 2 bath upper unit duplex. with outdoor 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 too Fantastic unit check our review

Guest favourite

Chalet in Killington

4.9 out of 5 average rating, 49 reviews

Kilbourne Lodge︙3BR/2BA＋Pets＋Fireplace＋Boot Dryer

Kilbourne Lodge is a classic mid-century ski chalet featuring a stunning stone accent wall, wood-burning fireplace, large picture windows, knotty pine walls & a quintessential mid-century angled roof. Vintage leather furniture, antique ski equipment, bathroom radiant floor heating & built-in boot dryer system round out this unique property! Ample parking & perfect central location off Killington Rd makes getting around a cinch! The lodge has 3 bedrooms & is best suited for families or couples.

Guest favourite

Chalet in Wells

4.97 out of 5 average rating, 69 reviews

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.

Guest favourite

Chalet in Killington

4.82 out of 5 average rating, 234 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

Our home is located on a quiet secluded road, just off Killington road, it's close to everything in Killington, the slopes, restaurants, bars & shops. It's the right side of a duplex with a large open living space that fosters great social interaction. We have 2-full-sized refrigerators, 24 PAIR SKI BOOT & GLOVE DRYER (Yes, dry gloves and boots every day), a private hot tub, sauna, wood stove, fire pit, 4 USB ports in every bedroom for charging, fresh linens & towels, a beautiful front yard

Guest favourite

Chalet in Killington

4.92 out of 5 average rating, 136 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!

Guest favourite

Chalet in Killington

4.99 out of 5 average rating, 91 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!!

Guest favourite

Chalet in Mendon

4.95 out of 5 average rating, 21 reviews

Cozy single family chalet close to Killington/Pico

Welcome to our boutique style mountain chalet nestled in tall birch trees. Our fully equipped modern home is 5 mins to Pico and 10 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 =).

Guest favourite

Chalet in Killington

4.96 out of 5 average rating, 24 reviews

Summer Getaway Spacious Beautiful Country Chalet

Relax around the large wood fireplace, enjoy a family weekend away. Killington/Pico ski resorts minutes away. Great place for kids. Gourmet kitchen, cathedral ceilings. 3 full baths. Rec room with ping pong and foosball Snowmobile? bring your sleds trails nearby plenty of driveway space to park trailers. During the summer months hike & bike right outside your door. 2 championship rated golf courses-Green Mtn National & Killington Resort 5 mins drive away.

Guest favourite

Chalet in Stockbridge

4.95 out of 5 average rating, 88 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 favourite

Chalet in Killington

4.87 out of 5 average rating, 228 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.

Superhost

Chalet in Mount Holly

4.94 out of 5 average rating, 53 reviews

Cozy 4BR/2BA Home near Okemo, Killington Mountains

Discover the ultimate mountain retreat at our spacious 4BR, 2BA home in Mt. Holly VT. Surrounded by lush woods, it's just minutes from Okemo & Killington Mountains. Relax on our big deck, soak in the hot tub, or enjoy indoor entertainment with 3 65" Smart TVs, a game room, Each room features a plush pillow-top bed with 1200 thread count sheets. Enjoy easy access to 103s, with a cleared driveway and pathways during snow. Plus, a fully fenced yard.