Chalet holiday rentals in Rutland County

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

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.

4.92 out of 5 average rating, 181 reviews

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

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

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

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 =).

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 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 mins from Lake St Catherine Park and country club and many hiking and mt-biking options for the active guests.

4.96 out of 5 average rating, 128 reviews

Chalet in Stockbridge

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.

4.87 out of 5 average rating, 248 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.

5 out of 5 average rating, 59 reviews

Chalet in Mount Holly

Cozy chalet mins from Okemo & VAST.

Come enjoy some time in our cozy & relaxing 3-bedroom, 2-bath home. If you prefer a winter or summer getaway, all the options are available. Minutes from all activities and restaurants. Enjoy the nearby hiking and biking trails, Okemo SP, Jackson Gore, Buttermilk Falls, Plymouth SP, and Echo Lake. Property located opposite mountain traffic. Hang a left on 103 when leaving JG/ Okemo Main Rd.

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space that's all yours, with room for everyone

Flats

Convenient locations with everyday essentials

Popular amenities for chalet rentals in Rutland County

Kitchen

Wifi

Free parking on premises

Air conditioning

Family-friendly chalet rentals

4.75 out of 5 average rating, 215 reviews

5BR Chalet in Historic Town bet Killington & Okemo

PamalaRating, 5 stars2 months ago

We had an issue with our previous rental and needed to find a place to stay that is pet friendly and available. Rad and Carol responded quickly to our reservation request. The house was made available to us early in the day and hot tub prepped last minute for us to enjoy! The Chalet is beautiful and spacious, the location is private and relaxing. The wood stove kept us warm and cozy while we enjoyed watching light snow fall. We would definitely stay there again and bring our family with us!

4.96 out of 5 average rating, 74 reviews

OZ- 6BR Ski Chalet Between Killington & Okemo

EmmaRating, 5 stars3 months ago

Wonderful stay - perfect location

4.82 out of 5 average rating, 76 reviews

Chalet in Ludlow

Mountain Chalet + HOT TUB

ChristopherRating, 5 stars3 months ago

Great place to stay for okemo mountain!! Very close to local restaurants and the mountain

Chalet in Pittsfield

4.95 out of 5 average rating, 56 reviews

Luxury Heart of VT Green Mountains

AbbyRating, 5 stars5 months ago

Fantastic place for a ski trip to Killington. Large and comfortable with plenty of room for 3 adults and 3 teens. We enjoyed the fireplace and hot tub. Communication was great. It was an easy drive to Killington. One of the best places we’ve stayed. We’d definitely stay there again.

4.87 out of 5 average rating, 75 reviews

West Park Chalet at Killington: Great For Groups!

DarleneRating, 5 stars3 months ago

We had a such a great time staying at Ed's property. Super close to the mountains - we went snowboarding every day, it was great! Ed was very responsive, and the house was kept clean. We really enjoyed the hot tub after a long day of snowboarding. Would highly recommend for big groups. Plenty of bed space.

Chalet in Ludlow

4.76 out of 5 average rating, 128 reviews

Charming Lakefront House

EricaRating, 5 stars3 months ago

This home was just what we were looking for. It is charming and spacious, rustic in all of the right ways, with a gorgeous view of the lake, and so close to Okemo. The master bedroom was huge, and we really enjoyed the large communal space with the wood-burning stove. Some of us were cooking while others were playing games, while others were relaxing by the fire, so that we could all easily enjoy each other‘s company. It was the perfect spot for a ski getaway. We all agreed we would love to stay there again.

Chalet in Castleton

4.65 out of 5 average rating, 26 reviews

Eckley Point Lake House

TimRating, 5 stars24 months ago

Guys weekend went smooth with no real hiccups. View and boat lift were great! Hopefully booking again next spring! 🎣⛳️😎

4.92 out of 5 average rating, 60 reviews

Chalet in Mount Holly

3 bedroom mountain getaway

DefneRating, 5 stars3 months ago

My friends and I had a great stay at Daniel’s place! It was very clean with plenty of space to accommodate all of us. We were skiing at Okemo, which was a quick 15 minute drive. Would definitely recommend staying here!

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Luxury chalet rentals

4.97 out of 5 average rating, 35 reviews

Summer getaway deck+bbq+chef’s kitchen+large yard

JillRating, 5 stars3 weeks ago

Second time staying here. Such a beautiful quaint and private location. The house is charming and has every amenity we needed for a long weekend. away. Leslie is a wonderful responsive host who is always very accommodating! Highly recommend 😊

5 out of 5 average rating, 26 reviews

Chalet in Mendon

Cozy Vermont Getaway minutes from Killington Mt.

StanleyRating, 5 stars5 months ago

Plenty of space for a ski trip for 12 people, would stay again!

4.87 out of 5 average rating, 67 reviews

Secluded 4BR cabin w/ HOT TUB- Walk to Access Rd!

CarolineRating, 5 stars3 months ago

Place was great, couple of minute drive to the mountain, nightlife was right around the corner and the accommodation had a ton of space.

Chalet in Ludlow

4.85 out of 5 average rating, 82 reviews

Okemo Mountain-Newly Renovated w AC, hottub, WiFi

KarenRating, 5 stars4 months ago

Brent’s house was beautiful and exactly as pictured. We loved the decor and it matched the mountain house feel. It was perfect for our family of 5 and we loved the board games in the living room. Very easy access to okemo to ski and to town. Recommend 4 wheel drive if you are coming in the winter as the roads and drive away could be a challenge without that! We hope to visit again next year!

4.94 out of 5 average rating, 48 reviews

Chalet in Stockbridge

BENT TREE Vermont, Mtn Chalet 25 min to Killington

PaulRating, 5 stars4 months ago

Beautiful location and very easy access to Killington Ski Resort! We had >1 foot of snow and the steep driveway was plowed well before departure. Very clear communication and instructions made for a very relaxing time. Thank you for sharing your home!

4.83 out of 5 average rating, 29 reviews

Hawk House

DylanRating, 5 stars4 months ago

A great spot for me and my friends to visit the great state of Vermont. Beautiful weather so the hot tub on the porch made for a great end of the day of skiing while it snowed. Overall, a wonderful stay

4.91 out of 5 average rating, 32 reviews

Chalet in Mount Holly

Cozy Chalet near Okemo Jacuzzi/Sauna

KellyRating, 5 stars3 months ago

My family and I had a great week at Gabriella's place in Mt. Holly. It is a 5 min drive from Jackson Gore Base at Okemo, which made for very easy skiing (and parking!). Gabriella was responsive and friendly when we checked in. We happened to be there during a snowstorm and the drive was plowed by midmorning the next day. It was also very cold, and despite the somewhat quirky heating, we were able to stay warm while at the house. My husband and daughter enjoyed the foosball in the basement (not heated, but does have plug in heater). Hot tub was great. Only thing guests might want to note is that there are limited pots and cooking supplies so it was challenging to make meals. Also, the dishes provided are melamine/not microwave safe so we bought paper plates for when we wanted to reheat food. The home is, however, well stocked with glasses, coffee cups, baking dishes, and pans. Beds were comfy. Heated mats on front steps were very helpful. All in all, a great stay and would rent again!