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Chalet vacation rentals in Plymouth

Find and book unique chalets on Airbnb

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Popular amenities for Plymouth chalet rentals

Family-friendly chalet rentals

Superhost
A secluded chalet is surrounded by snow-covered trees, showcasing its wrap-around deck. The winter landscape features undisturbed snow blanketing the ground, while blue skies peek through scattered clouds above.
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
A spacious living area features vaulted wooden ceilings with exposed beams, allowing natural light to fill the room. Comfortable couches are arranged around a central coffee table, with a large television set against the wall. Light-colored curtains frame the windows, enhancing the inviting ambiance.
Chalet in Killington
4.84 out of 5 average rating, 251 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

ScottRating, 5 stars3 weeks ago
This is our second time renting Clinton's ski lodge place is great super host. Always responsive will be renting again next season.
Guest favorite
A rustic ski chalet is nestled among snow-covered trees, with a sloping driveway leading to the entrance. The building showcases a wooden deck and vibrant blue exterior, surrounded by a serene winter landscape.
Chalet in Ludlow
4.82 out of 5 average rating, 76 reviews

Mountain Chalet + HOT TUB

ChristopherRating, 5 stars3 months ago
Great place to stay for okemo mountain!! Very close to local restaurants and the mountain
Guest favorite
A three-level chalet is shown, featuring a wooden exterior and a spacious front deck with chairs. Large windows provide natural light, while surrounding trees create a natural backdrop. A gravel path leads to the entrance, and a grassy area is visible in the foreground.
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
Superhost
Chalet in Jamaica
4.86 out of 5 average rating, 94 reviews

Pickleball Pool Golf 7min-Stratton DogsOK Fire Pit

DanielRating, 5 stars3 months ago
Our stay was fantastic. The house was conveniently located relative to Stratton mountain, very comfortable, and the host was fantastic
Top guest favorite
The spacious A-frame home is set against a backdrop of vibrant trees and lush greenery. A well-manicured hill leads to the house, which features large windows allowing natural light to fill the interior. The bright blue sky complements the tranquil outdoor scenery.
Chalet in Dover
4.97 out of 5 average rating, 113 reviews

Grey Wolf's Den: 5 miles to Mount Snow w/HOT TUB

CaterinaRating, 5 stars3 months ago
Great location! This was a two family trip up to Mt Snow. We had a wide range of ages and 2 dogs. The house had plenty of toys and things for the kids to do - their favorite was the scavenger hunt! The kitchen is one of the best stocked kitchens compared to other Airbnbs we have used. The beds were comfortable - plenty of extra pillows and blankets. The couch and chairs in the living area were also very comfortable. The hot tub was very nice and enjoyable after everyone went skiing.
Guest favorite
The charming chalet is framed by lush greenery, showcasing a blend of stone and wood exterior. Bright windows with shutters open to a spacious yard, while a deck leads to the entrance. Seasonal decorations add a welcoming touch to the garden area.
Chalet in Dover
4.92 out of 5 average rating, 306 reviews

A charming VT chalet

carolynRating, 5 stars1 week ago
Mary was a super good hostess and she even left us a welcome basket full of goodies including Bogle red wine (cabernet), coffee, and other treats plus homebred brownies in the fridge! We loved the chalet and the beauty of it inside and out with the greenery of the forest and the brook which our dog, Beau, got right into it and loved it! We all enjoyed the area and the cozy home with the room to spread out and hear the rain as we were snug inside. The bed we chose to sleep in was comfy and warm and I (Carolyn) loved having coffee on the deck of a morning with Beau. We enjoyed our long walks down the road and the town of Dover was fun to visit as well as the beautiful wedding we attended over Wilmington not far away. It was a wonderful stay and we certainly love Vermont! This was our 4th stay in Vermont between the years of 2004 - now. Our first "Dog Vacation" took us to Brattleboro, Middlebury, Willoughvale with Lake Willoughby, and last summer to White River Junction and Barre. Fun!
Guest favorite
The exterior of the upper unit duplex is surrounded by snow, showcasing a wooden deck with a railing and steps leading to the entrance. A prominent stone chimney rises from the roof, and large windows provide a view of the surrounding forest.
Chalet in Stockbridge
4.92 out of 5 average rating, 181 reviews

Killington ski house winter MTbike -new jacuzzi

ZachRating, 5 stars3 months ago
Great place to stay! The hot tub after a long day of snowboarding was amazing. Dean responds fast to any questions you have too. Definitely recommend

Luxury chalet rentals

Guest favorite
A well-lit living room features a spacious sectional sofa facing a fieldstone fireplace. A wooden coffee table sits centrally, and a Samsung flat-screen TV is mounted above the fireplace. Large windows provide natural light and views of the surrounding greenery, enhancing the serene setting.
Chalet in Killington
4.96 out of 5 average rating, 109 reviews

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

AlixRating, 5 stars3 months 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.
Top guest favorite
Chalet in Dover
5 out of 5 average rating, 35 reviews

Charming Mountain Chalet w/ Spa near Mt Snow

Caitlin Rating, 5 stars2 months ago
Lovely stay in a cozy, comfortable house only 15 minutes from Mount Snow. We enjoyed post ski-day nights by the fire, with plenty of comfortable seating and board games galore. The yard was great for our dogs and features like the koi pond and hot tub were easy to enjoy in a peaceful and private environment. We’ll be back!
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 stars1 month 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
A wooden deck is featured, showcasing a pair of woven chairs and a small table. The natural surroundings are visible through large windows and greenery creates a serene backdrop. The structure exudes a rustic charm, inviting relaxation in the fresh air.
Chalet in Stockbridge
4.94 out of 5 average rating, 48 reviews

BENT TREE Vermont, Mtn Chalet 25 min to Killington

PaulRating, 5 stars4 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 Stratton
4.96 out of 5 average rating, 138 reviews

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

MeghaRating, 5 stars2 weeks ago
My girlfriends and I came here for a weekend (Friday night-Sunday morning) just to have a peaceful weekend away and it was delightful! The house was absolutely stunning, had every amenity we could ever need, and was so peaceful. I was so bummed that it rained all weekend (we managed to slip into the hot tub in between rain squalls) because we wanted to utilize all the fun outdoor stuff, but we still had such a good time keeping ourselves entertained inside with how spacious and stocked the house was with games, a fireplace, and a tv in the upstairs living room. Overall it was a very relaxing weekend for us all and we didn’t have to worry about a thing. Also, the little convenience store down the street was so helpful and stocked with plenty of produce that we thought we would have to go to a grocery store for! Definitely recommend going there if you forget any cooking foods you may need, as we were pleasantly surprised. Definitely book if you have the chance - thank you Josh!
Top guest favorite
An inviting open-concept living area features wooden beams and large windows, allowing for natural light. A spacious cream sofa, accent chairs, and a round coffee table create a comfortable seating arrangement. A well-equipped kitchen is visible in the background, along with a dining area for gatherings.
Chalet in Winhall
5 out of 5 average rating, 50 reviews

Summer Fun in Winhall! Family Game Room & Deck!

BryanRating, 5 stars1 month 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
The living room offers ample seating with a large arrangement of light-colored sofas surrounding a central wooden coffee table. Natural light floods the space through large windows, complemented by a warm wooden floor and soft area rugs. Decorative pillows add subtle touches of comfort.
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!
Guest favorite
A serene waterfall cascades over smooth, large rocks into a clear pool. Surrounding greenery includes vibrant trees and lush vegetation, providing a tranquil natural setting. Sunlight reflects off the water's surface, highlighting the clarity and pebbled texture below.
Chalet in Mount Holly
4.94 out of 5 average rating, 77 reviews

Cozy 4BR/2BA Home near Okemo, Killington Mountains

JesseRating, 5 stars3 weeks ago
Our stay was terrific! We unfortunately didn’t have the best weather but no better place to be stuck inside. The house was very well thought out, everything we could have needed was there and easy to find. We traveled with pets and the house was very dog friendly, the fenced in yard connecting to the porch was such a great feature. The rooms were very clean and comfortable. The hosts were very helpful, upon arrival I did not have the code to enter and with in a minute they had reached out through the door bell service and made sure we got in! Couldn’t be happier with our stay!

Lakefront chalet rentals

Guest favorite
A serene waterfront scene is captured, showcasing calm, reflective waters framed by lush greenery. A cozy seating area with striped cushions is positioned nearby, inviting relaxation. In the distance, a family enjoys time on the water while the sun filters through the trees.
Chalet in Antrim
4.93 out of 5 average rating, 104 reviews

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

CarolRating, 5 stars3 weeks ago
Very great place to take a break and a leisure with the family, quiet place and great house
Guest favorite
A serene lakeside scene showcases a wooden dock extending into clear waters, with several boats anchored nearby. A shaded umbrella rests over a small table, offering a cozy spot for relaxation. Lush green trees line the opposite shore, enhancing the natural setting.
Chalet in Hubbardton
4.94 out of 5 average rating, 96 reviews

Chalet 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.
Guest favorite
The exterior of the lakefront home features a large deck with multiple seating areas including red Adirondack chairs. The architecture is a distinctive A-frame design with large windows, allowing natural light to fill the interior. Surrounding greenery enhances the serene environment.
Chalet in Sunapee
4.94 out of 5 average rating, 81 reviews

Lake Sunapee Get Away

LaurieRating, 5 stars2 weeks 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.
A wooden dock extends into the calm waters of Lake Rescue, reflecting surrounding trees and distant hills. The serene landscape is framed by greenery, with a clear blue sky overhead. A boat is visible at the edge of the image, alongside a boathouse.
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 Plymouth

  • Total rentals

    10 properties

  • Nightly prices starting at

    R2,704 ZAR before taxes and fees

  • Total number of reviews

    1.1K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

Destinations to explore

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  4. Windsor County
  5. Plymouth
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