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Chalet vacation rentals in Killington

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Popular amenities for Killington chalet rentals

Family-friendly chalet rentals

Guest favorite
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 favorite
Chalet in Waitsfield
4.96 out of 5 average rating, 141 reviews

Warm Luxury Mid-Century Modern Chalet

CaitlinRating, 5 stars2 weeks ago
This is the second time I’ve stayed at Sierra’s house, and we just love it! It’s comfortable, beautiful, Waitsfield is lovely, and we couldn’t have asked for anything else!
Guest favorite
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 favorite
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
Superhost
Chalet in Granville
4.81 out of 5 average rating, 89 reviews

Hilltop 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
Superhost
Chalet in Jamaica
4.78 out of 5 average rating, 452 reviews

Chalet 7min to Ski Stratton-WoodStove,Views,DogsOK

KarenRating, 5 stars1 week ago
We had a great time at the cabin. Although there are other cabins on the property, it felt private. The space was very roomy and comfy. We loved the record player, and I looked at every record and played many of them! We took our own sheets and towels, but all that was at the cabin when we got there, so we didn't need them. It was nice to find empty kitchen cupboards for our own stuff, so we didn't have to rearrange everything :) And we've had a run of vacation rentals with foot high grass lately, so it was nice to see Jason mowing the lawn on our third day there. All in all, it was a great stay
Guest favorite
Chalet in Ludlow
4.95 out of 5 average rating, 128 reviews

Okemo Ski Chalet with Hot Tub

WillRating, 5 stars3 weeks ago
Stop scrolling, you found your next vacation. Bob is a fantastic host with a stunning home. We have stayed with Bob many times and he continues to invest in the property and ensures your stay is nothing short of fantastic. Cannot recommend the ski chalet enough.
Guest favorite
Chalet in Peru
4.85 out of 5 average rating, 89 reviews

Bromley Aframe - King Master Bed, Wood Fireplace

SamanthaRating, 5 stars1 month ago
All around a wonderful experience. Michael was lovely, super responsive and went out of his way to make sure we were comfortable. The house and amenities are well appointed. Bed was super comfy. Would absolutely stay again.

Luxury chalet rentals

Top guest favorite
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 favorite
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.
Top guest favorite
Chalet in Killington
4.99 out of 5 average rating, 70 reviews

The Overlook - AC | Hot Tub | View | Fires | Games

KevinRating, 5 stars3 weeks ago
Oh my God the views! Super cute place with plenty of room and awesome hosts. The hot tub is nice (but SUPER chlorinated, which was a little annoying, but I get it). The kitchen is STOCKED with gadgets and cookware, which is super convenient. Also, killer location: great restaurants less than a mile away in Killington village and Rutland only 20 min away. Everything was clean and tidy and the whole family had an absolute blast. Will definitely come back.
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 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 favorite
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 favorite
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.
Top guest favorite
Chalet in Winhall
5 out of 5 average rating, 50 reviews

Summer Fun in Winhall! Family Game Room & Deck!

BryanRating, 5 stars3 weeks ago
This was an enjoyable stay. Slept 6 comfortably. We also had such a great time in the game room playing pool, watching tv, and utilizing the arcade games. Totally recommend!
Superhost
Chalet in Mount Holly
4.91 out of 5 average rating, 32 reviews

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!

Lakefront chalet rentals

Guest favorite
Chalet in Antrim
4.94 out of 5 average rating, 102 reviews

Direct Waterfront A-Frame, Close to 3 Ski Areas!

ScottRating, 5 stars2 weeks ago
Very peaceful and quiet location. Had all the amenities and is well furnished. Not much need to leave the property but still close enough to small towns with shops and many nice hikes. Seems like a great place to stay any time of year. Our dog was able to swim right from the deck which was nice.
Guest favorite
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.
Guest favorite
Chalet in Sunapee
4.94 out of 5 average rating, 81 reviews

Lake Sunapee Get Away

LaurieRating, 5 stars6 days ago
Thank you so much for a wonderful stay! The view was spectacular on every level! Lake Sunapee is a very special place, and meant a lot to be able to stay here. Excellent communication and very helpful instructions. The house is well equipped with everything. Beds are so comfortable. Plenty of room to spread out. Quiet and peaceful, loved looking at the lake! Thank you again so much for everything!
Top guest favorite
Private room in Bridgewater
4.99 out of 5 average rating, 172 reviews

MT Retreat / Killington, Woodstock, Rutland, Okemo

NicolaRating, 5 stars2 months ago
Linda and Ted are very welcoming hosts and have a beautiful home. We had a great weekend and would definitively consider going back.
Guest favorite
Chalet in Fort Ann
5 out of 5 average rating, 30 reviews

Gorgeous Lakefront Lake George Area Chalet

JessicaRating, 5 stars7 months ago
This home was beautiful, the photos do not do it justice, perfectly decorated! We had 3 families that compromised of 6 boys and there was PLENTY of space, each family took a floor and the boys were outside the whole time either fishing, catching crawfish, or in the paddle boat, they had a blast! Also, the kitchen was surprisingly well stocked with all your needs and more! We had such an amazing time here and are looking forward to come back next year!
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.

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