Chalet vacation rentals in Killington

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Popular amenities for Killington chalet rentals

Family-friendly chalet rentals

Guest favorite
Chalet in Peru
4.9 out of 5 average rating, 63 reviews

Getaway in Green Mountains

AndrewRating, 5 stars2 months ago
We stayed here with another couple and their dog two years back and had a wonderful time. I am so grateful that we came back this year with our dog, Chili, and she had the absolute best time! Old Manchester rd is really quiet and is great for off leash walks. Chili loved frequently seeing the other neighbors and their dogs (who were all friendly) on her walks. We’re also runners and so the road is great for running (mostly flat, minimal traffic, frequently plowed, amazing views of Bromley). Jennifer and Dan are both very friendly too. Jennifer did a good job of reaching out to us often making sure we had what we needed. Dan often came by to plow the driveway which was really nice too. Our last day was during a snow storm and they were flexible with checkout which was really helpful. This place really has everything you need and the location is excellent (close to Stratton, Manchester which has a dog park, and downtown Peru which has an outdoor ice skating rink
Superhost
Chalet in Plymouth
4.75 out of 5 average rating, 215 reviews

5BR Chalet in Historic Town bet Killington & Okemo

PamalaRating, 5 stars3 weeks 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!
Superhost
Chalet in Killington
4.73 out of 5 average rating, 11 reviews

Luxury of large space by ski slopes, deck HOT TUB

SandaRating, 5 stars49 months ago
Our stay at Hideaway was relaxing and exactly how we expected it. The cabin is within a short driving distance from the ski areas and grocery stores, and very comfortable for a family with two children. The host was easy to reach and responded quickly to communication. Overall, a wonderful vacation.
Top guest favorite
Chalet in Pittsfield
5 out of 5 average rating, 54 reviews

Mountain Bliss: Spacious Retreat Near Killington

WilliamRating, 5 stars1 month ago
This place is a lovely spot that exceeded expectations for me and my friends! The host was super communicative throughout the whole process, from right after booking through checkout. It’s an amazing place and I would definitely stay here again.
Guest favorite
Chalet in Ludlow
4.82 out of 5 average rating, 76 reviews

Mountain Chalet + HOT TUB

ChristopherRating, 5 stars1 month 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 stars1 month 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.
Top guest favorite
Chalet in Woodstock
4.98 out of 5 average rating, 105 reviews

Falcon House: VT Chalet w/Sauna, Bike to Village

VanessaRating, 5 stars1 month ago
Enjoyed everything about our stay. Beautiful property, loved the sauna and ability to snowshoe right out the door. Quaint and nicely decorated. Plenty of privacy, room for guests including extra parking. Had nearly 12 inches of snow while there, quite the winter wonderland. Quickly plowed, shoveled and sanded when needed. Oversized windows and unique architecture made it all extra special. Will definitely return. Perfect for any season.
Guest favorite
Chalet in Mount Holly
4.92 out of 5 average rating, 60 reviews

3 bedroom mountain getaway

DefneRating, 5 stars1 month 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!

Luxury chalet rentals

Guest favorite
Chalet in Killington
4.96 out of 5 average rating, 109 reviews

4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!

AlixRating, 5 stars1 month ago
We had a great weekend skiing at Killington and hanging at this lovely mountain house. The house was perfect for a group of couples. We loved the big open kitchen, huge sectional couch, and the hot tub. It was a 5 minute drive to many restaurants and fun bars, and a 7 minute drive to Killington lifts - super convenient and easy! We would definitely stay here again.
Guest favorite
Chalet in Winhall
4.92 out of 5 average rating, 36 reviews

1970's Classic Ski Chalet - Stratton Mountain

CaraRating, 5 stars2 months ago
The 70’s chalet is its name sake! Cozy and close to the mountain. The fireplace and downstairs room make it a great after ski relaxation spot! And it’s 5 minutes to Stratton Mountain!
Superhost
Chalet in Warren
4.79 out of 5 average rating, 48 reviews

Chalet In The Clouds - MT views, private trails

SamRating, 5 stars1 month ago
Great spot to stay and excellent view of the valley. The main floor is a great space for gathering!
Guest favorite
Chalet in Winhall
4.89 out of 5 average rating, 79 reviews

Spacious Chalet W/ Endless Entertainment THE BARN

LuisRating, 5 stars1 month ago
The property was spacious, clean, and well-equipped to accommodate our large group comfortably. Perfect for relaxing after a day on the slopes. The location was ideal, just a couple minutes drive from the ski resort. Bobby, the host, was incredibly responsive and helpful!. We couldn't have asked for a better place for our ski weekend and would highly recommend it to anyone looking for a great group getaway!
Superhost
Chalet in Warren
5 out of 5 average rating, 4 reviews

Scenic Getaway: Unique Large Home with Views!

LouisRating, 5 stars7 months ago
Beautiful place with beautiful view! Close enough to Warren in bike and it was fun to discover the area! House was clean and had everything. The insinkerator switch was closed so we had issues with the sink but other than that, everything was amazing! Jacuzzi water wasn’t clean and had a weird smell, although it didn’t really bother us but it would be great to verify its maintenance!
Top guest favorite
Chalet in Stockbridge
4.94 out of 5 average rating, 48 reviews

BENT TREE Vermont, Mtn Chalet 25 min to Killington

PaulRating, 5 stars2 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!
Guest favorite
Chalet in Winhall
4.96 out of 5 average rating, 95 reviews

Minutes to Stratton! Large, private home w. sauna

AliciaRating, 5 stars2 months ago
We had a wonderful stay at Zach and Tasha’s place. Perfect house for our 2 families with kids. Close to Stratton Mountain. Very clean house and well equipped. The sauna was our favorite part! Will come back for sure!
Top guest favorite
Chalet in Winhall
4.98 out of 5 average rating, 97 reviews

Mountain view chalet with hot tub & fire pit!

JaymeRating, 5 stars2 weeks ago
Breathtaking views and 5 Star Host! My husband and I wanted to give our son and his friends a remote trip to Vermont. Ryan, our host, was so helpful and went above and beyond to make my son’s 18th birthday “guy’s trip” a success. We truly felt right at home and every single picture looks exactly like the property. Thank you Ryan-you’ve set a high bar.

Lakefront chalet rentals

Guest favorite
Chalet in Sunapee
4.94 out of 5 average rating, 80 reviews

Lake Sunapee Get Away

WyattRating, 5 stars2 months ago
Carl was a great host and extremely responsive. He helped make the check in/out process extremely easy and was extremely responsive with any questions. There was snow shovels and salt to deal with snow which was helpful. He helped navigate an issue right away and was very generous with offering help even though he was somewhat unavailable. The house was a great location and very clean, and could accommodate a large group easily. The open floor plan for the kitchen/dining room/living room was very nice and we enjoyed the new range for cooking. Carl even helped to make sure we forgot something that we left at the house after contacting us that it was there! Overall, I would highly recommend staying here.
Top guest favorite
Private room in Bridgewater
4.99 out of 5 average rating, 172 reviews

MT Retreat / Killington, Woodstock, Rutland, Okemo

NicolaRating, 5 stars1 month ago
Linda and Ted are very welcoming hosts and have a beautiful home. We had a great weekend and would definitively consider going back.
Chalet in Ludlow
4.76 out of 5 average rating, 128 reviews

Charming Lakefront House

EricaRating, 5 stars2 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.
Guest favorite
Chalet in Hubbardton
4.94 out of 5 average rating, 96 reviews

Chalet on Pristine Beebe Lake

ConnieRating, 5 stars7 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.

Quick stats about chalet rentals in Killington

  • Total rentals

    50 properties

  • Nightly prices starting at

    ﺩ.ﺇ220 before taxes and fees

  • Total number of reviews

    3K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Rutland County
  5. Killington
  6. Chalet rentals