
Chalet vacation rentals in Rutland County
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Top-rated chalet rentals in Rutland County
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Popular amenities for Rutland County chalet rentals
Family-friendly chalet rentals
Guest favorite

Chalet in Plymouth
4.75 out of 5 average rating, 215 reviews5BR 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 favorite

Chalet in Plymouth
4.96 out of 5 average rating, 74 reviewsOZ- 6BR Ski Chalet Between Killington & Okemo
EmmaRating, 5 stars3 months ago
Wonderful stay - perfect location
Guest favorite

Chalet in Ludlow
4.82 out of 5 average rating, 76 reviewsMountain Chalet + HOT TUB
ChristopherRating, 5 stars2 months ago
Great place to stay for okemo mountain!! Very close to local restaurants and the mountain
Superhost

Chalet in Granville
4.81 out of 5 average rating, 89 reviewsHilltop Chalet on 20 rolling acres
PaulRating, 5 stars8 months ago
My wife and I thoroughly enjoyed our stay at John's Chalet. The house was exactly as described beautiful inside and out. We loved seeing all the wildlife around the home every day. The home is very private and close to many outdoor activities especially hiking. We would certainly consider this home again on our next trip to Vermont. Sincerely Paul & Rebecca

Chalet in Ludlow
4.76 out of 5 average rating, 128 reviewsCharming 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 otherās 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 reviewsEckley 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! š£ā³ļøš
Guest favorite

Chalet in Mount Holly
4.92 out of 5 average rating, 60 reviews3 bedroom mountain getaway
DefneRating, 5 stars3 months ago
My friends and I had a great stay at Danielās 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 favorite

Chalet in Hubbardton
4.94 out of 5 average rating, 96 reviewsChalet 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 reviewsChalet 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 favorite

Chalet in Killington
4.97 out of 5 average rating, 35 reviewsClassic Ski Chalet+ wood fireplace+chefās 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 š

Chalet in Pittsfield
4.95 out of 5 average rating, 56 reviewsLuxury 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 weāve stayed. Weād definitely stay there again.
Guest favorite

Chalet in Mendon
5 out of 5 average rating, 26 reviewsCozy Vermont Getaway minutes from Killington Mt.
StanleyRating, 5 stars4 months ago
Plenty of space for a ski trip for 12 people, would stay again!
Guest favorite

Chalet in Mendon
4.96 out of 5 average rating, 26 reviewsPico/ 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 Killington
5 out of 5 average rating, 22 reviewsKillington 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!
Top guest favorite

Chalet in Killington
4.98 out of 5 average rating, 80 reviewsChateau 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.
Guest favorite

Chalet in Pittsfield
4.86 out of 5 average rating, 37 reviewsThe Sklarzhaus
StevenRating, 5 stars3 months ago
We really enjoyed staying at Fionaās place for our ski trip to Killington. The house was warm and inviting when we arrived. The beds were comfortable and clean. The kitchen and living room gave us plenty of space for us to stretch out.
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- Stratton Mountain
- Sugarbush Resort
- Okemo Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- West Mountain Ski Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Dartmouth Skiway
- Lake George Expedition Park
- Fort Ticonderoga
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Autumn Mountain Winery
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Hooper Golf Course
- Cozy Cottages & Otter Valley Winery
- Montshire Museum of Science
- Gooney Golf
- Adirondack Extreme Adventure Course
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