Chalet vacation rentals in Rutland County

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Top-rated chalet rentals in Rutland County

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Superhost

Chalet in Plymouth

4.75 out of 5 average rating, 200 reviews

5BR Chalet in Historic Town bet Killington & Okemo

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 Vermont between Killington & Okemo 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 (please inquire)

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 Wells

4.98 out of 5 average rating, 84 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 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/snowshoeing trails right from the house. This home offers open living room with hard wood floors, dining area, kitchen with large island, family room, gas stove, mudroom/laundry area.

Superhost

Chalet in Killington

4.9 out of 5 average rating, 145 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 Killington

4.98 out of 5 average rating, 101 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 favorite

Chalet in Plymouth

4.96 out of 5 average rating, 101 reviews

Ledges Unit: Hot Tub, two miles 2 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 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 Mendon

5 out of 5 average rating, 22 reviews

Unique Luxury-Minutes to Skiing-Hidden Speakeasy

Luxury Ski Chalet in a GREAT location ❄️10 MINUTES TO ALL THE ACTION IN KILLINGTON ❄️5 MINUTES TO THE BASE OF PICO ❄️15 MINUTES TO THE K1 OR SKYSHIP GONDOLAS IN KILLINGTON ❄️SECRET BOOKCASE DOOR HIDING A LARGE, WELL-EQUIPPED SPEAKEASY ❄️NO CLEANING FEE ❄️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 BUT REMOTE

Guest favorite

Chalet in Killington

5 out of 5 average rating, 53 reviews

BearHaus- HUGE Hot Tub, 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.

Guest favorite

Chalet in Stockbridge

4.95 out of 5 average rating, 110 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.