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Chalet holiday rentals in Woodstock

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Popular amenities for chalet rentals in Woodstock

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 stars1 month 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 Killington
4.84 out of 5 average rating, 250 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

MauraRating, 5 stars3 weeks ago
Nice space for a group, plenty of room for dining and relaxing. Clint was very responsive and gave excellent instructions. Appreciated the hospitality!
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 stars50 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.
Guest favourite
Chalet in Waitsfield
4.96 out of 5 average rating, 140 reviews

Warm Luxury Mid-Century Modern Chalet

Meg & RobRating, 5 stars2 months ago
Sierra is extremely responsive, understands the ski mentality and very considerate of our group. Thank you so much, we enjoyed spending quality time by the fireplace and of course the super close by Mad River Glen access!!!!!!
Guest favourite
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 Jamaica
4.78 out of 5 average rating, 445 reviews

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

OscarRating, 5 stars4 days ago
Beautiful place, real quaint and nice to stay at. The surroundings were real nice at nice and the nature was very nice to be surrounded by. All the amenities worked as expected and the beds were comfortable. The porch was our favorite place to relax at; hammock, yard, stereo playing from inside. Great stay … thanks Jason and Sara :))))
Guest favourite
Chalet in Ludlow
4.94 out of 5 average rating, 126 reviews

Okemo Ski Chalet with Hot Tub

KatieRating, 5 stars4 weeks ago
Bob’s place is great for several families. Many bedrooms, multiple bathrooms, great amenities and close to skiing!
Top guest favourite
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.

Luxury chalet rentals

Superhost
Chalet in Killington
4.9 out of 5 average rating, 162 reviews

Kingsbrook: Chalet w Sauna, Hot Tub, AC!

AndrewRating, 5 stars3 weeks ago
This was the second time we stayed here and had a great time. The location is great and the house is well maintained and comfortable. We'll definitely be returning!
Top guest favourite
Chalet in Mendon
5 out of 5 average rating, 45 reviews

Luxury Chalet Close to Skiing, Golf, and Weddings

KateRating, 5 stars6 days ago
This house was a really special find. It is very thoughtfully designed and feels comfortable and clean. Extra special touches like the record player, shuffleboard, and giant kids' bunk room make it unique. We loved roasting marshmallows at the outdoor fire pit, checking the little creek for frog's eggs, and cooking in the spacious kitchen. Host communication was thorough and easy too. Great find!
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.
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 favourite
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!
Guest favourite
Chalet in Wardsboro
4.88 out of 5 average rating, 42 reviews

Indoor Hot Tub Chalet | Firepit Fun Near Mt Snow

KellyRating, 5 stars1 month ago
We really enjoyed our stay! The house is beautiful and perfect location for skiing at Mt snow or Stratton. Indoor hot tub was a huge hit & spacious living spaces were great for spending quality time together!
Guest favourite
Chalet in Stratton
4.96 out of 5 average rating, 132 reviews

Luxe HOT TUB, SAUNA 8–12 min Stratton & Mount Snow

BethanyRating, 5 stars1 day ago
We adored our stay! It was perfect for our group. The sauna and hot tub were a massive hit. The hosts are wonderful. On a stormy night we lost power and Josh quickly reached out to check-in give us power company updates and let us know the generator would do its thing which it did beautifully. Would love to come back with my family and enjoy further relaxing and peaceful moments together in the mountains!

Lakefront chalet rentals

Guest favourite
Chalet in Antrim
4.94 out of 5 average rating, 97 reviews

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

TruthRating, 5 stars1 day ago
The house is exactly as advertised. All the amenities you’d want/need for a little vacation. The hot tub is great
Guest favourite
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.
Guest favourite
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 favourite
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.

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