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Chalet holiday rentals in Rutland County

Find and book unique chalets on Airbnb

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Popular amenities for chalet rentals in Rutland County

Family-friendly chalet rentals

Superhost
Chalet in Plymouth
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!
Guest favourite
Chalet in Plymouth
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
Guest favourite
Chalet in Ludlow
4.82 out of 5 average rating, 76 reviews

Mountain Chalet + HOT TUB

ChristopherRating, 5 stars3 months ago
Great place to stay for okemo mountain!! Very close to local restaurants and the mountain
Superhost
Chalet in Killington
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.
Superhost
Chalet in Granville
4.81 out of 5 average rating, 90 reviews

Hilltop Chalet on 20 rolling acres

MelRating, 5 stars2 weeks ago
Another wonderful stay at The Chalet! The property and home are beautiful, very quiet and peaceful. We look forward to coming back every year. Plenty of space for a big family, and our dogs enjoy playing outside.
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

JRating, 5 stars20 months ago
La maison correspondait au descriptif, endroit très calme au bord du lac, équipement complet, jeux, kayak à disposition, nous avons passé un agréable moment en famille. Merci Georgina de nous permis de partir plus tard. Bon souvenir!
Guest favourite
Chalet in Hubbardton
4.94 out of 5 average rating, 96 reviews

Chalet on Pristine Beebe Lake

ConnieRating, 5 stars9 months ago
This property was the most peaceful stay I have ever had. So quiet and relaxing. It was the perfect getaway while we were in town for a wedding. The stay had everything we needed to make dinners for the family and a wonderful porch overlooking Lake Beebe. Thanks for sharing your space with my family and me. Side note: Dylan was very successful fishing in this lake and the boats made it easy to explore the lake.

Luxury chalet rentals

Chalet in Plymouth
4.8 out of 5 average rating, 41 reviews

Chalet Schlosser

JeremyRating, 5 stars4 months ago
Chalet Schlosser was perfect for our short vacation week excursion. Plenty of beds for a couple families, super cozy, and everything worked as advertised, including the fireplace which kept us warm and helped dry our gear. Really convenient to Killington lodges, easy drive to town, driveway was plowed and cleaned during a storm while we were there without needing to ask about it. The "chalet" was the cherry on top of a great weekend.
Chalet in Stockbridge
4.95 out of 5 average rating, 38 reviews

Private Mountain Sanctuary | 15 Min to Killington

CoreyRating, 5 stars2 weeks ago
One of the best locations in the northeast, period. The 360 degree mountain top view is unmatched. The home is beautiful and well connected via solar and starlink, so while we could unplug, it was also possible to reply to emails and get some work done. 11/10
Top guest favourite
Chalet in Killington
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 😊
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.
Guest favourite
Chalet in Mount Holly
4.93 out of 5 average rating, 67 reviews

Okemo Hot Tub Fireplace Billiard

ChristopherRating, 5 stars3 months ago
Our stay was awesome! The driveway was icy but the hosts provided salt for us to use and the snow-pile guy came during our week and spread sand which was very helpful. The house was huge and provided lots of activities and room for everyone to spread out. We had some amazing family dinners using the well equipped kitchen and large dining space.
Guest favourite
Chalet in Mendon
4.96 out of 5 average rating, 26 reviews

Pico/ Killington chalet, minutes to the mountain

MelissaRating, 5 stars4 months ago
The home was the perfect getaway for a weekend of snowboarding. Enough space for everyone to have their own area but also cozy enough to be all together, perfect mix of both. Absolutely would recommend to anyone looking to be close to the mountain and all the other amenities the Killington/Pico area has to offer.
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!
Top guest favourite
Chalet in Stockbridge
4.94 out of 5 average rating, 48 reviews

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!

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