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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

Guest favourite
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 stars2 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.
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! 🎣⛳️😎
Guest favourite
Chalet in Mount Holly
4.92 out of 5 average rating, 60 reviews

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!
Guest favourite
Chalet in Hubbardton
4.94 out of 5 average rating, 96 reviews

Chalet on Pristine Beebe Lake

ConnieRating, 5 stars8 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 stars3 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.
Top guest favourite
Chalet in Killington
4.97 out of 5 average rating, 35 reviews

Classic Ski Chalet+ wood fireplace+chef’s kitchen

JillRating, 5 stars2 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 😊
Guest favourite
Chalet in Mendon
5 out of 5 average rating, 26 reviews

Cozy Vermont Getaway minutes from Killington Mt.

StanleyRating, 5 stars4 months ago
Plenty of space for a ski trip for 12 people, would stay again!
Chalet in Killington
5 out of 5 average rating, 22 reviews

Killington Ski Chalet on Great Eastern Trail

SherryRating, 5 stars17 months ago
This house is amazing! Our family Killington trip was enhanced by staying at this beautiful chalet. The pictures online do not do this property justice as it is much more beautiful in person! The kitchen is very well stocked with everything you need, the house was clean and immaculate with enough linens for everyone. Virginia was responsive to any questions and very welcoming. We had a snowstorm, and the plow came promptly to plow the driveway. There is an echo from the loft in the main floor, and it is much quieter on the lower level. There was ample wood for the fireplace. We would love to come again next year!
Chalet in Ludlow
4.85 out of 5 average rating, 82 reviews

Okemo Mountain-Newly Renovated w AC, hottub, WiFi

KarenRating, 5 stars3 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 stars3 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!
Top guest favourite
Chalet in Killington
4.98 out of 5 average rating, 80 reviews

Chateau Charmaine - Big Hot Tub - No Cleaning Fee

WillRating, 5 stars2 weeks ago
Of all the places I've stayed, this is the best one by far. This house is very unique, spacious and relaxing and exceeded all of our expectations. This house has a record player with cool records. Does anything more need to be said after that?!? Well, yes! There is a fire ring behind the house, the house is in a very peaceful setting and the hot tub is amazing, the furniture and beds are clean and comfortable, the kitchen had everything you could possibly ever want and . . . this is the most cozy house ever, with individual thermostats for each room and each bathroom too, plus a nice and blazing pellet stove in the living room which is super easy to use. Whoever designed and built this place was a true master of space. And the hosts were the most responsive and kind - hats off to hosts Jared & Corey for such a great place! We will be back someday.
Top guest favourite
Chalet in Killington
5 out of 5 average rating, 71 reviews

BearHaus Central AC, HUGE Hot Tub, Awesome FirePit

JenniferRating, 5 stars3 weeks ago
I’ve stayed at this home multiple times, and it’s always a pleasure. The neighborhood is quiet and peaceful, making it a perfect place to relax. The host is incredibly welcoming and makes the entire process smooth and stress-free. The house is always clean, well-maintained, and stocked with everything I need. I always look forward to staying here and would highly recommend it to anyone looking for a comfortable and reliable Airbnb.

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