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

5.0 out of 5 average rating, 36 reviews

The Overlook | Hot Tub | Game Room | 5min to MTN

Escape to stunning mountain views at The Overlook. 5 min from Killington Resort, restaurants, and shops. Enjoy the peacefulness of the private cozy mountain chalet after a long day of adventure and unwind in the hot tub, game room, or by the fireplace. 4WD/AWD and good snow or all-season tires are required to access the chalet on the steep hillside in the winter. 🏔️ Mountain view 🌄 Large decks and balcony 🏖️ Hot tub ⚽️ Game room 🍗 Propane grill 🍳 Fully stocked kitchen 🪵 Fire pit 🔥 Fire table

Aug 14 – 21

G$129,136 GYD per night

Guest favorite

Chalet in Killington

5.0 out of 5 average rating, 117 reviews

Luxury, AC, 6 BR, 12 Beds, 3 Bath, Hot Tub, Yard

CEDARWALK at Killington, a luxury 6 BR, (12 beds) 3 BA home, with AC, for up to 14 people. 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

Aug 27 – Sep 3

G$220,662 GYD per night

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

May 7 – 14

G$46,171 GYD per night

Guest favorite

Chalet in Wells

4.97 out of 5 average rating, 68 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.

Oct 1 – 8

G$96,636 GYD per night

Guest favorite

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

Oct 15 – 22

G$51,244 GYD per night

Guest favorite

Chalet in Killington

4.92 out of 5 average rating, 133 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!

Jun 2 – 9

G$71,676 GYD per night

Guest favorite

Chalet in Killington

4.99 out of 5 average rating, 90 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!!

Oct 2 – 9

G$104,121 GYD per night

Guest favorite

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 =).

Jun 5 – 12

G$58,886 GYD per night

Guest favorite

Chalet in Hubbardton

4.93 out of 5 average rating, 92 reviews

Chalet on Pristine Beebe Lake

Chalet is located at south end of lake Beebe with late afternoon sun and great sunset views. Sailboat, paddle boat, canoe, rowboat, kayaks, paddle board, Life vests, swim float with diving board during the summer, check availability after Oct 1st. Tennis and Pickleball at a private court nearby. A complete list of all amenities can be emailed. PLEASE NOTE: Most essentials are supplied except sheets, bath and beach towels and can be supplied at additional $10 per guest on request.

Mar 4 – 11

G$53,997 GYD per night

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.

Sep 27 – Oct 4

G$58,594 GYD per night

Guest favorite

Chalet in Killington

4.9 out of 5 average rating, 159 reviews

Close to Mountain and walk to restaurants!

Killington Mtn is 1.4 miles away, so the Sports Park is an easy drive. The area offers skiing, snowboarding, tubing, hiking, biking, kayaking, ATVing, PLUS two excellent golf courses nearby. Restaurants and shops are walking distance. The house is casual and comfortable, located on a quiet dirt road with nice views of the valley from the upstairs and deck. There is a HOT TUB and SAUNA and linens included. We also have full weeks available upon request at a substantial discount.

Jul 1 – 8

G$48,980 GYD per night

Guest favorite

Chalet in Killington

4.95 out of 5 average rating, 121 reviews

Treehouse Lodge in heart of Killington

Enjoy vacation in the Treehouse lodge with a true northeast mountain house experience. Located off the access road of one of Vermonts most active mountains, experience three seasons of prime New England fall foliage, Vermont's best snow trails, and summer events and hiking. This sleek, uniquely designed lodge offers a comfortable living room, spacious bedrooms, clean bathrooms, and fully stocked kitchen allowing guests to feel at home away from home.

May 9 – 16

G$76,058 GYD per night