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Chalet vacation rentals in Wilmington

Find and book unique chalets on Airbnb

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Popular amenities for Wilmington chalet rentals

Family-friendly chalet rentals

Guest favorite
A gravel driveway leads toward a charming wooden house surrounded by trees in autumn foliage. Greenery and colorful leaves create a welcoming entrance as the home is partially visible in the background.
Chalet in Wilmington
4.95 out of 5 average rating, 98 reviews

Rustic Sunny Vermont Home near Mount Snow

AndreaRating, 5 stars3 months ago
Couldn't say enough great things about both the hosts and the property. Just lovely home - very spacious, and clean and cosy. The area is gorgeous, with a lot to do. Mt. Snow and Hermitage skiing are very close, and Wilmington and the area are charming. Host was very gracious and kind..thank you!
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 stars2 months ago
Great place to stay for okemo mountain!! Very close to local restaurants and the mountain
Superhost
The exterior of a large chalet is showcased, featuring a steeply pitched roof and expansive windows. A wraparound deck provides access to the outdoors, surrounded by lush greenery. The structure exhibits a dark wood finish that contrasts with the clear blue sky.
Chalet in Granville
4.81 out of 5 average rating, 89 reviews

Hilltop Chalet on 20 rolling acres

PaulRating, 5 stars7 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
A rustic chalet is surrounded by a spacious lawn, featuring natural stone elements and several outdoor seating areas. A fire pit is situated in the center, accompanied by Adirondack chairs. The front porch is visible, providing access to the inviting entrance of the home.
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
A contemporary ski house is featured, set against a snowy landscape. The structure showcases large glass windows and a spacious deck, elevated on stilts. Surrounding trees and a light dusting of snow enhance the serene atmosphere of the property, inviting a cozy retreat.
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.
Superhost
Chalet in Jamaica
4.86 out of 5 average rating, 94 reviews

Pickleball Pool Golf 7min-Stratton DogsOK Fire Pit

DanielRating, 5 stars2 months ago
Our stay was fantastic. The house was conveniently located relative to Stratton mountain, very comfortable, and the host was fantastic
Superhost
A spacious living area features high wooden ceilings with large windows allowing natural light to fill the room. Comfortable seating includes two armchairs and a striped sofa, with decorative pillows enhancing the inviting arrangement. A gas fireplace is situated on a stone hearth, adding warmth to the space.
Chalet in Wilmington
4.57 out of 5 average rating, 91 reviews

Cozy House - Mount Snow, VT

VincyRating, 5 stars4 months ago
Mariah’s cabin was perfect for our getaway. Lots of natural light, clean and had everything we needed. It was a quick drive to Mt Snow and close to some cute restaurants in Wilmington. I was given clear and very lengthy instructions for check in/check out and Mariah was responsive to some minor questions we had throughout our stay. I missed the opportunity to book the hot tub/clubhouse when we first made the reservation. Hoping future guests don’t make the same mistake and be sure to request it at the time of booking!
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.

Luxury chalet rentals

Guest favorite
Chalet in Dover
5 out of 5 average rating, 48 reviews

Authentic Vermont Chalet: Year Round Vacation Home

ChristinaRating, 5 stars3 months ago
Beautiful spot with a cozy yet spacious house. Instructions were very clear on how to get in and the different features of the house. Perfect for a relaxing get-away with friends!
Top guest favorite
Chalet in Wilmington
5 out of 5 average rating, 62 reviews

Beautiful Home on 22 Acres w/Ponds & Central A/C

Christopher WRating, 5 stars1 month ago
Beautiful place. The house, the land. My family of 5 and our dog loved it. The kids loved the ponds and the games room. Vanessa was a great host and helped make it a great experience from start to finish. Cheers!
Top guest favorite
The exterior of the chalet is presented, showing a dark wooden structure surrounded by trees. A spacious deck is highlighted with string lights, creating a warm ambiance. Large windows offer glimpses of the interior, reflecting the surrounding greenery.
Chalet in Sunderland
4.99 out of 5 average rating, 80 reviews

Serene & Stylish Chalet + HOT TUB near Manchester

TimRating, 5 stars1 week ago
Garrett was responsive and allowed us to check in early as his Chalet was cleaned and ready for us early. Great host!! Welcome basket with hoodies and a host note to our group. Great!!
Guest favorite
The exterior of the A Frame home features large windows that allow light to fill the space, showcasing the wooden interior. A visible spiral staircase leads to the loft. Outdoor seating areas are arranged on the deck, surrounded by snow, creating a cozy atmosphere.
Chalet in Dover
4.98 out of 5 average rating, 63 reviews

A quintessential Vermont getaway

LauraRating, 5 stars3 months ago
Linda was awesome! She was super responsive and helpful. We ran into several snags with our trip due to weather but we kept in constant communication and it all worked out. The house is cute and has a certain charm to it. The hot tub wasn't working but that was communicated to us a day before so we were aware. The bathrooms are a bit small, particularly the showers. Overall we had a great trip. Very close to Mt Snow. Quiet and scenic location. Fireplace was nice to have. We replenished with kindling and dry wood just so we could keep a nice warm fire going. Lovely host & lovely home.
Superhost
An inviting kitchen area features a sleek bar with four stools, accompanied by a cozy seating area. Large, bright windows provide views of the surrounding trees, bringing natural light into the space. Rustic wooden accents enhance the welcoming ambiance.
Chalet in Dover
4.8 out of 5 average rating, 5 reviews

Relaxing Retreat in the Heart of Dover

KaitlynRating, 5 stars1 week ago
This Airbnb was the perfect fit for my group and I while we visited Vermont. The house was located in a great area where it was close to everything you would need or want to visit. The house was also very spacious for my group and very clean.
Guest favorite
An outdoor fire pit is surrounded by wooden Adirondack chairs, set against a backdrop of a spacious cabin. The cabin features large windows that enhance the view of the surrounding autumn foliage and a sprawling yard, inviting relaxation and outdoor gatherings.
Chalet in Wardsboro
5 out of 5 average rating, 12 reviews

Modern Lux Cabin w/ Mtn Views | Fire Pit

ChanaRating, 5 stars4 weeks ago
This house was perfect for our weekend family trip! The space was beautifully designed, thoughtfully laid out, and on the most wonderful peaceful and quiet road. It was a true Vermont mountains experience. The host was extremely responsive and helpful. We all loved it. Would recommend to anyone and definitely stay again.
Top guest favorite
A charming chalet is nestled among lush forest greenery, featuring a spacious deck adorned with soft lighting. A hot tub is prominently placed for relaxation, while large glass doors invite the warmth of the interior living space to mingle with the outdoors.
Chalet in Wilmington
5 out of 5 average rating, 94 reviews

Mt Snow Chalet: Peaceful Escape w/Hot Tub

AmyRating, 5 stars1 month ago
We loved the Snow Chalet!! Such beautiful surroundings and well appointed. The beds were super comfy and the black out shades were great for the kids. Location was great and close to the grocery stories. Wilmington is a sweet town too with lots of cool shops. The club house pool was warm and the pool was nice and toasty. An awesome trip!
Top guest favorite
The chalet is positioned on a gently sloping grassy area, featuring a spacious deck with a hot tub and several outdoor seating options arranged around a fire pit. Large windows reflect warm interior light, framing a serene natural backdrop of trees, enhancing the inviting ambiance.
Chalet in Winhall
4.98 out of 5 average rating, 101 reviews

Mountain view chalet with hot tub & fire pit!

AndyRating, 5 stars6 days ago
We really enjoyed our stay; the house was ideally situated in a private, wooded area and yet just a few minutes drive into Manchester. The views from the house were spectacular. The house had a cozy mountain chalet feel and yet equipped with a very modern kitchen. We took advantage of both the fire pit and the hot tub.

Lakefront chalet rentals

Top guest favorite
Chalet in Orange
5 out of 5 average rating, 27 reviews

Spectacular Lakefront 3br House, AC, private beach

DonnaRating, 5 stars8 months ago
OMG Beautiful! Walking into the gorgeous house, we didn't know whether to look inside or outside first! The inside is lovely, clean and neat without unnecessary clutter. The outside is spacious and beautiful. The house and property were described perfectly. Washer & dryer worked well. The pool table downstairs could easily be used without waking anyone in the house. When the owner learned we would be traveling with an infant, she made sure to have a highchair, crib, and infant life jacket in the house. The house is safe for babys. There isn't space to list all that we loved about this house. It has become part of our reunion week wonderful memories. Did I mention that the house was spotless and the grounds immaculate (except for the falling leaves which was part of the beauty!) I would happily stay here again and again and again.
Superhost
A spacious deck features multiple seating options, including two wicker chairs, positioned for leisurely views. Large windows provide a connection to the interior spaces, and natural wood flooring complements the outside setting. The entrance door is visible, adding functionality to the outdoor area.
Chalet in Winchester
4.86 out of 5 average rating, 125 reviews

Chalet Sonsie: A Sweetwater Stay

VanessaRating, 5 stars2 weeks ago
Our stay at Patti’s chalet was incredible! The home itself is beautiful and the view of the lake is breathtaking. It is a very quiet and peaceful neighborhood, which we enjoyed walking around every morning. It is also conveniently located—only 20 minutes to downtown Keene. The home is clean and boasts modern amenities. Our favorite features were the decks, fireplace, spacious kitchen, comfy couch, and the game room. The arcade and foosball table were so much fun. This stay was the perfect combination of rest, relaxation and fun. Patti was a very responsive host. We would definitely stay again!
Top guest favorite
A charming wooden house is set amidst lush greenery, featuring a sloped roof and large windows that allow natural light to fill the interior. A porch with rocking chairs welcomes relaxation, while a stone path leads up to the entrance, enhancing the inviting ambiance.
Chalet in Rindge
5 out of 5 average rating, 22 reviews

Adirondack Cabin & Sauna on Lake Monomonac

ShannonRating, 5 stars1 day ago
…We loved it so much, we extended our stay another night! This is hands down one of THE best Airbnb’s I’ve stayed in worldwide. We fell in love with the cabin, and the setting is simply beautiful. Jim couldn’t have been a better host. I look forward to coming back!
Guest favorite
A charming A-frame cabin is surrounded by tall evergreen trees, with a wooden deck accessible by stairs leading to the entrance. Snow blankets the ground, and large windows provide a view of the interior, creating a cozy, inviting exterior impression.
Chalet in Sunapee
4.94 out of 5 average rating, 81 reviews

Lake Sunapee Get Away

LaurieRating, 5 stars5 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!
Superhost
The living area features wood-paneled ceilings and large windows allowing natural light to fill the space. A spacious dining table with wooden chairs is centrally located. A cozy seating area is arranged around a circular coffee table, providing a comfortable environment for gatherings.
Chalet in Rindge

3 Cabins & Sauna on Lake Monomonac

AllisonRating, 5 stars2 months ago
Jim’s place is a dream!! The photos don’t do it justice. These cabins are so cute and cozy, and even on our rainy/snowy weekend in March we had a fantastic stay. Views are gorgeous and the setting feels private and peaceful. Jim was super friendly and kindly set up the sauna for us to use. Everyone was comfortable and the cabins were very clean. Check in/out was easy and convenient. Our group really enjoyed it and would definitely stay again!!
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 Wilmington

  • Total rentals

    30 properties

  • Nightly prices starting at

    G$23,080 GYD before taxes and fees

  • Total number of reviews

    1.8K reviews

  • Family-friendly rentals

    30 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. Windham County
  5. Wilmington
  6. Chalet rentals