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Ski-in/Ski-out vacation rentals in Bennington County

Find and book unique ski-in/ski-out homes on Airbnb

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Popular amenities for Bennington County ski-in/ski-out rentals

Ski-in/ski-out house rentals

Superhost
A fire pit area is surrounded by six green Adirondack chairs, set within a natural landscape of fallen leaves and trees. In the background, a spacious two-story home features expansive glass windows and a large deck, providing a welcoming outdoor space.
Home in Jamaica
4.93 out of 5 average rating, 15 reviews

The Mountain Escape

DanRating, 5 stars3 months ago
Great space! We were comfortable with a big group here, and loved being so close to the slopes. Hot tub seems new and is in great condition.
Guest favorite
A blue wooden chalet is surrounded by greenery, featuring large glass windows that provide views of the interior. A small outdoor deck leads to a hot tub, positioned against the backdrop of vibrant autumn foliage.
Home in Dover
5 out of 5 average rating, 14 reviews

Private chalet tucked in the green mountains

Zach & CourtneyRating, 5 stars2 months ago
Liz's place was the great! Beautiful, clean, and conveniently located to the mountain. Everything we needed for a long ski weekend with friends! Thank you!
Top guest favorite
A row of three-story townhouses presents a winter scene under a clear blue sky. Snow blankets the roofs and surrounding landscape, with large windows reflecting the sunlight. The architecture features peaked roofs and chimneys, suggesting a charming mountain retreat.
Home in Dover
5 out of 5 average rating, 5 reviews

Mt Snow Townhouse - Ski On/Off

BarbaraRating, 5 stars3 months ago
We had a great stay at Matthew's. he was so helpful getting us situated and settled in. The space has everything needed for a cozy winter stay. Perfect Family set up
Guest favorite
A bright living area features a large window offering views of lush greenery and distant mountains. Comfortable sofas are arranged around a wooden coffee table, accompanied by a floor lamp and a decorative plant, creating a welcoming space for relaxation.
Home in Winhall
4.92 out of 5 average rating, 26 reviews

Multi-Level Ski Retreat at Stratton Mountain

LiliaRating, 5 stars4 months ago
We had a wonderful stay Duojia’s residence! Peaceful location, clean, and the Stratton Mountain view was icing on the cake. There is privacy and so much space at this home. Thank you!
Top guest favorite
The exterior of the home is shown, featuring a charming porch illuminated by string lights. Adirondack chairs offer a cozy seating area amidst well-tended greenery and a gravel driveway. A backdrop of trees and a clear sky suggests a tranquil setting.
Home in Wilmington
5 out of 5 average rating, 30 reviews

Rustic home near skiing & lakes, walk to downtown

KassRating, 5 stars1 week ago
Very welcoming home, amenities were a great way to entertain ourselves during the night while kids were sleeping. The spacious living room, dining room and kitchen were an absolute dream! Would stay here again!
Superhost
An outdoor seating area features a round table surrounded by four metal chairs. A vibrant flower pot adds color, while a tall planter with greenery stands beside a large window, allowing natural light to brighten the space. The deck offers a serene view of the surrounding trees.
Home in Wardsboro
4.71 out of 5 average rating, 77 reviews

Ski Mountain Snow&Stratton

StephaniaRating, 5 stars3 months ago
Daisy was extremely friendly and responsive. She accommodated a later check out because my snowmobiling tour got delayed to later in the day and she was very understanding and let us check out at 1PM instead of 11AM. The place is so cute and aesthetically put together. The hammock and jacuzzi is the best!!
A red, two-story house is surrounded by greenery, featuring a green metal roof and multiple windows reflecting natural light. A spacious deck extends from the upper level, while a front entryway is accessible via stairs. The yard is lush with grass and trees.
Home in Dover
5 out of 5 average rating, 6 reviews

Spacious 6 Bedroom home on the resort at Mt. Snow

LifangRating, 5 stars20 months ago
Staying at this Airbnb was a fantastic experience! The property was clean, well-maintained, and exactly as described in the listing. The arcade game was a big hit for the kids. During our stay, we felt right at home, and the communication with the host was excellent. Ron was quick to respond to any questions we had. We had a wonderful time, and if we ever visit again, we would definitely stay here.
Guest favorite
An open living space features a cozy seating area with a large sectional sofa facing a stone fireplace. A dining table is positioned nearby, surrounded by black chairs. Natural light floods the room through oversized windows, showcasing a Christmas tree adorned with decorations.
Home in Wilmington
4.89 out of 5 average rating, 27 reviews

Brand new, 5 BR, next to Hermitage Club&Hermt Inn

MargaretRating, 5 stars9 months ago
We loved this house! And plan to come back again soon! Beautiful home with great amenities. Host was very responsive. We had a great visit!

Family-friendly, ski-in/ski-out home rentals

Top guest favorite
A living space showcases two striped sofas and an armchair arranged around a wooden coffee table. A fireplace sits beneath a wall-mounted television. Large windows allow natural light, while light-colored furnishings create a comfortable atmosphere.
Condo in Dover
4.95 out of 5 average rating, 21 reviews

Slopeside at MT Snow VT

KristynaRating, 5 stars4 months ago
Perfect location to get on and off the mountain. Responsive and helpful. We had a great weekend!
A comfortable living area showcases two sofas and a chair arranged around a central coffee table. Natural light enters through large windows, framing views of the lush greenery outside. A lamp and decorative accents add warmth to the space near the fireplace.
Townhouse in West Dover
4.65 out of 5 average rating, 51 reviews

Mt. Snow, VT scenic views, 3decks

AnthonyRating, 5 stars39 months ago
Great place! Clean, spacious, with plenty of amenities. Owner was great. Flexible. Communicated clearly and promptly. Would definitely stay again.
A cozy studio condo is featured, showcasing a warm interior with wood-paneled walls. A large screen TV and a wooden dining set are present. A bunk bed is situated next to a full-size bed, while a fireplace adds a welcoming touch to the space.
Condo in Peru
4.9 out of 5 average rating, 20 reviews

Summer or Winter Slope side on Bromley Mountain!

MicheleRating, 5 stars40 months ago
Talk about great location! This was the best ski-in/ski-out condo we've used. Bonus: the sledding hill is at the end of the parking lot. The beds were very comfortable and the fireplace was easy and so cozy. Corinne was very attentive and took care of any questions promptly.
A living area displays a comfortable green sectional sofa facing a wooden coffee table. Natural light filters through sheer curtains at the large windows. A stone fireplace is positioned against one wall, complemented by wooden furniture and a lamp providing additional lighting.
Condo in Dover
4.59 out of 5 average rating, 34 reviews

Summer Living On Hillside Condo on Mount Snow

RyanRating, 5 stars9 months ago
We had a nice getaway at Paul's place. The place fit our needs perfectly. We enjoyed the use of both the indoor and outdoor pool. You do need to reserve times online for use of the pools or other activities but we never had any issue with that. There are several great restaurants nearby and we enjoyed walking the nearby trails and shopping in Wilmington and Dover.
Guest favorite
The wooden cabin is enveloped in a serene winter landscape, with smoke rising gently from the chimney. Snow blankets the ground, and trees dot the backdrop. A front porch extends along the cabin, providing a welcoming entrance. A snowmobile is parked nearby.
Cabin in Woodford
4.98 out of 5 average rating, 145 reviews

Stone's Camp on Stamford Stream

ThomasRating, 5 stars7 months ago
This was our second stay at Stone's Camp. It was just as great as the first stay. It's very private, peaceful and relaxing. We enjoyed hiking around the area and never had to leave the property in our car during our 4 night stay. The walk from the camp down the abandoned road to the washout is perfect. Our dogs enjoyed being off leash and exploring the woods and stream. It was especially nice for our 15 yro dog who is now unable to tackle larger hikes. Nights were spent enjoying a campfire by the babbling stream on rain free nights. Rainy nights were spent playing cards and games around the table indoors. If you are looking for something quiet, private and love to be outside and away from it all this is the place for you. If you have dogs it's the place for them as well. Thank you again, Chuck, for sharing your piece of paradise and thanks for accommodating our daughter and her boyfriend at the last minute who surprised us with a visit from the West Coast. We hope to be back!
The exterior of a three-story house is presented, showcasing a gray facade with a pitched roof. Large windows allow natural light into the interior. Surrounding shrubs and small trees add greenery to the property, complementing the seasonal foliage in the background.
Townhouse in Stratton
4.86 out of 5 average rating, 51 reviews

Stratton Mountain House

SusanRating, 5 stars27 months ago
We stayed with four adults and two young children. The beds were great - we all had excellent separate spaces. The common room was spacious as was the dining area. It was easy to walk to the shuttle bus pick-up spot. Chris was so great to let us stay a bit later on Sunday to enable us to ski a bit and then organize ourselves for departure.
Superhost
A historic red farmhouse and adjacent barn are set against a clear blue sky, surrounded by lush green grass. Stone pathways lead to the house, highlighting the inviting porch, while vibrant foliage borders the property.
Home in Whitingham
4.93 out of 5 average rating, 70 reviews

The Amos Brown House.

PeterRating, 5 stars3 months ago
This is a really special antique house that has been very well cared for. we visited in the midst of pretty narly presidents dy snow storm and the howling winds and multiple feet of snow outside only made the old house feel even cozier and more special. in the winter, the house sits on the end of a dirt road, due to the southern portion of it being covered in snow so we were nervous that we would get completely snowed in, but the town plowed the road multiple times each day and we had no problems getting in and out! Our big highlights were cross country skiing on the trail that crosses the property, puzzling by the gas fireplace, and the huge mounds of dog toys for our pup! Also, big thank you to Michelle for being so accommodating about our late check out. Our time here makes me want to check out all of the landmark trusts locations!
A rustic barn house is framed by green trees, featuring a bright red metal roof. The wooden exterior has aged gracefully, with windows partially visible. A garden area with flowering plants is noted in the foreground, alongside a small stone wall, set against an expansive green field.
Home in Landgrove
5 out of 5 average rating, 23 reviews

Landgrove Charm - Post and Beam Barn House

DavidRating, 5 stars5 months ago
We stayed there over New Year’s, and it was beautiful, peaceful, and extremely comfortable. The host and caretaker were very responsive and helpful. We would definitely stay there again!

Ski-in/ski-out condo rentals

Guest favorite
A spacious dining area features a long wooden table that seats eight, complemented by modern light fixtures. Large windows allow natural light to fill the room, while a sliding glass door offers access to a private outdoor space. A console cabinet is visible against the wall.
Condo in Dover
5 out of 5 average rating, 15 reviews

Slopes N Seasons | Trailside Condo at Mount Snow

AlexanderRating, 5 stars2 months ago
We loved our stay! Everything was immaculate. New. Even ready with some fun board games and a Bluetooth speaker. The location was excellent, and we had a great time! We definitely recommend and would stay again.
Superhost
A private deck is shown, furnished with two blue chairs placed beside a wooden railing. The view includes a serene landscape of trees and patchy snow, indicative of the changing seasons.
Condo in Dover
4.92 out of 5 average rating, 12 reviews

Renovated Condo - 5 min walk to Mount Snow

Christoph GRating, 5 stars2 months ago
beautiful condo, well maitained and bathrooms new and remodeled. Great location to the ski lifts. He woks great, walls are solid because we couldn't hear the neighbors and all units were full this weekend. Nice fireplace and wifi worked great for the kids and all big flat screen tv's were excellent. Easy kitchen to cook in for the whole family. Best condo we've stayed at in Mt. Snow. Owners answered all our questions and recommendations
Top guest favorite
The living area features a spacious sectional sofa arranged around a coffee table, complemented by a cozy wood-burning fireplace. Natural light fills the room through large windows, which overlook the snowy landscape. A dining table for six and a media console housing a Smart TV are also present.
Condo in Stratton
4.98 out of 5 average rating, 41 reviews

Ski In/Out, Cozy 3BR Condo steps to Village

MatthewRating, 5 stars2 months ago
Exactly as described. Beautiful condo, right in the heart of Stratton. Easy ski in/ski out. Excellent proximity to everything the village has to offer. The kitchen is well equipped and the bedrooms are really comfortable. Brian was a great host! We will absolutely book again for future Stratton ski trips!
Superhost
A cozy living area features two brown leather sofas arranged around a wooden coffee table, which holds an assortment of magazines and a board game. A staircase leads to the upper loft, while large mirrors enhance the sense of space.
Condo in Stratton
5 out of 5 average rating, 4 reviews

Stratton Slopeside Retreat

Wei-YingRating, 5 stars4 months ago
We were looking for a fun ski weekend with friends and Sierra’s place was perfect. Close to the Tamarack lift, it was great for ski-in/ski-out. The unit was cozy with plenty of room. It had everything we needed and we’re already looking forward to next year! ⛷️
Superhost
A cozy living area features a stone fireplace framed by a wooden mantel. Comfortable brown seating is arranged around a small table, with a large window providing natural light and views of the surrounding greenery. A television and a decorative fireplace tool set enhance the space.
Condo in Dover
4.88 out of 5 average rating, 8 reviews

Seasons on Mount Snow | Walk Out / Ski Home!

JohnRating, 5 stars2 months ago
It was exactly how described by management and pics. We felt at home and kitchen had everything one needs. Greg the manager was incredibly responsive and professional…. We would go back.
Guest favorite
A prominent sign displaying the Long Trail House logo features crossed ski poles and imagery of the mountains, set against a patterned green background. Snow is visible on the ground, and large windows of the building can be seen in the background.
Condo in Stratton
4.9 out of 5 average rating, 20 reviews

Stratton Duplex Condo Steps to Lifts, Village!

NathalieRating, 5 stars2 months ago
Great walkable location. Loft space granted nice privacy for 2 couples or extended family. Fireplace and living room were cozy.
Guest favorite
A cozy living area features a mix of orange and brown sofas, complemented by a wooden coffee table. A stone fireplace is positioned beneath a wooden panel wall, with a television mounted nearby. Large windows illuminate the space, offering views of the snowy outdoors.
Condo in Dover
4.89 out of 5 average rating, 9 reviews

Pool & hot tub! Hiking, nature and mountain views!

ToniRating, 5 stars3 months ago
We loved the proximity to Mount snow, and the layout of the place was cozy and comfortable. We loved the newly renovated kitchen and all kitchen supplies were new. We didn’t get to use the amenities but we loved the sauna and hot tub offerings!
Guest favorite
A cozy living area is highlighted by a stone fireplace, topped with a wooden mantle. A large television is mounted on one wall, while plush seating surrounds a wooden coffee table. Stacked firewood is neatly arranged beside the fireplace, adding to the warm ambiance.
Condo in Dover
5 out of 5 average rating, 23 reviews

Lyon Family Lodge - Ski-in/ski-out

BethRating, 5 stars5 months ago
Great location, ski on ski off and very nice community not far from restaurants. Jared was very responsive and flexible with check in time. Overall a great condo on the mountain and would stay here again.

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