Chalet vacation rentals in Rutland County

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Top-rated chalet rentals in Rutland County

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Guest favorite

Chalet in Killington

4.83 out of 5 average rating, 235 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!

Guest favorite

Chalet in Stockbridge

4.93 out of 5 average rating, 175 reviews

Killington ski house winter 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 favorite

Chalet in Killington

4.88 out of 5 average rating, 56 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 favorite

Chalet in Wells

4.98 out of 5 average rating, 82 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 favorite

Chalet in Mendon

5 out of 5 average rating, 19 reviews

Unique Luxury- Secret Door-Minutes to Ski Resorts

Luxury Ski Chalet in a GREAT location! ❄️NO CLEANING FEE ❄️5 MINUTES TO THE BASE OF PICO ❄️10 MINUTES TO ALL THE ACTION IN KILLINGTON ❄️15 MINUTES TO THE K1 OR SKYSHIP GONDOLAS IN KILLINGTON ❄️SECRET BOOKCASE DOOR HIDING A LARGE, WELL-EQUIPPED SPEAKEASY ❄️MASSIVE THEMED KIDS ROOM ❄️TWO MASTER BEDROOMS WITH PRIVATE BATHROOM ACCESS ❄️THOUGHTFUL AMENITIES FOR LARGE FAMILIES SEEKING COMFORT, LUXURY, AND FUN ❄️INCREDIBLY COMFORTABLE BEDS AND LINENS ❄️CONVENIENT BUT REMOTE- 4 WHEEL DRIVE RECOMMENDED

Guest favorite

Chalet in Killington

4.92 out of 5 average rating, 144 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 favorite

Chalet in Plymouth

4.96 out of 5 average rating, 101 reviews

Ledges Unit: Hot Tub, 2 mi to Skyeship Gondola

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

Chalet in Mendon

4.96 out of 5 average rating, 24 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 favorite

Chalet in Wells

4.89 out of 5 average rating, 137 reviews

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

We Welcome events like weddings and filming! 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 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

Guest favorite

Chalet in Mount Holly

4.92 out of 5 average rating, 51 reviews

3 bedroom mountain getaway

This beautifully updated three bedroom, two bathroom ranch on 3+ acres is surrounded by mountain wilderness. The VAST trail can be accessed right off the property. You are only a few steps away from incredible skiing/boarding, hiking, fishing, swimming, road cycling. There are over twenty miles of biking/hiking trails next to our house. This home offers open living room with hard wood floors, dining area, kitchen with large island, family room, gas stove, mudroom/laundry area.

Guest favorite

Chalet in Killington

5 out of 5 average rating, 126 reviews

Luxury, AC, 6 BR, 12 Bed, 3 Bath, Hot Tub, privacy

CEDARWALK at Killington, a luxury 6 BR, (12 beds) 3 BA home, with AC, Heart of Killington, three levels, 2 living rooms, great yard! 6/7 person HOT TUB on the deck with tons of privacy, Cathedral ceilings, huge Windows for great views, open living spaces! Perfect for entertaining. Renovated inside and out with upscale decor and comfortable beds. bluetooth SONOS sound. Certified with Vermont Fire Safety. Whole house water filtration. Cedarwalk Killington, killingtonLIFE

Guest favorite

Chalet in Stockbridge

4.95 out of 5 average rating, 107 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.