
Chalet vacation rentals in Woodstock
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Top-rated chalet rentals in Woodstock
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Popular amenities for Woodstock chalet rentals
Family-friendly chalet rentals

5BR Chalet in Historic Town bet Killington & Okemo
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!

Luxury of large space by ski slopes, deck HOT TUB
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.

Warm Luxury Mid-Century Modern Chalet
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!!!!!!

Mountain Bliss: Spacious Retreat Near Killington
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.

Mountain Chalet + HOT TUB
Great place to stay for okemo mountain!! Very close to local restaurants and the mountain

Chalet 7min to Ski Stratton-WoodStove,Views,DogsOK
The quiet retreat in Vermont, just like we wanted. We are already comfortable with country living, so being here was easy and peaceful.

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

3 bedroom mountain getaway
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

Kingsbrook: Chalet w Sauna, Hot Tub, AC!
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!

4+BR pet-friendly w/ hot tub & Stratton parking!
Great house, as described. Very responsive host before and during the stay with clear instructions. The couple of things that stood out: 1. Big house; easily sleeps 10, can get a couple more kids in if you want. 2. 15 minutes to Stratton with a parking permit provided which was key. 3. Indoor garage space was great, especially as it was snow storming outside. Kitchen had everything you'd want. Snow was plowed early in the morning. Stayed with wife and 2 teenage daughters and 2 dogs. Would come back. Thank you!

Chalet In The Clouds - MT views, private trails
Great spot to stay and excellent view of the valley. The main floor is a great space for gathering!

Spacious Chalet W/ Endless Entertainment THE BARN
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!

Scenic Getaway: Unique Large Home with Views!
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!

Indoor Hot Tub Chalet | Firepit Fun Near Mt Snow
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!

Luxe HOT TUB, SAUNA 8-12 min Stratton & Mount Snow
So hyggelig! Hygge House is 100% what it promises. Wonderful, peaceful place to escape the busy life for a few days and relax in a beautiful house in a beautiful forest. Hot tub, sauna, cosy house, surrounded by nature. Near all activities of Stratton area. We even got five inches of new snow making it winter wonderland in April.

Mountain view chalet with hot tub & fire pit!
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

Direct Waterfront A-Frame, Close to 3 Ski Areas!
Thank you, was a great stay and an amazing experience with Emily as the host

Chalet on Pristine Beebe Lake
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.

Lake Sunapee Get Away
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.

MT Retreat / Killington, Woodstock, Rutland, Okemo
Linda and Ted are very welcoming hosts and have a beautiful home. We had a great weekend and would definitively consider going back.

Charming Lakefront House
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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- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Pats Peak Ski Area
- Owl's Nest Resort
- Ragged Mountain Resort
- Tenney Mountain Resort
- Mount Snow Ski Resort
- Hooper Golf Course
- Baker Hill Golf Club
- Veterans Memorial Recreation Area Ski Hill
- Fort Ticonderoga
- Dartmouth Skiway
- Northeast Slopes Ski Tow
- Mount Sunapee Resort
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Ekwanok Country Club
- Killington Adventure Center
- Santa's Land USA
- Whaleback Mountain