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

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

Top-rated ski-in/ski-out rentals in Bennington County

Guests agree: These ski-in/ski-out homes are highly rated for location, cleanliness and more.

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Guest favourite
Condo in Dover
4.89 out of 5 average rating, 114 reviews

SKI IN/OUT @ Mount Snow (Hot Tub & Pool)

Escape to Seasons on Mount Snow & stay in our fully equipped 2 bedroom (ski in/out) condo. Our location is the best on the mountain ... right between the main face & Carinthia Freestyle Park! Enjoy the log burning fire (wood provided), smart TV & boardgames plus the fabulous Seasons on Mount Snow facilities where you can relax in a hot tub, pool or sauna. See below for info on activities in the warmer months including hiking, biking, scenic rides, lakes, golf, camp, a spa & the fall colors!

Top Guest favourite
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, 54 reviews

Ski In/Out, Cozy 3Bed condo steps to Village

Mountain Watch is one of the most sought after locations in Stratton due to its proximity to the lifts, shops and restaurants. This comfortable ski-in, ski-out home is well suited for family getaways and trips with close friends. Tasteful furnishings, wood burning fireplace and lift and mountain views from the deck and living room await your stay here. Comfortably sleeps 7, but can fit 8. There is a sleeper pullout chair in the king bedroom, and also a pack-n-play crib for the youngest guests.

Superhost
A cozy living area features a dark gray sofa with decorative cushions, complemented by two wooden armchairs. A timber-framed window offers a view of the outdoors. A coffee table holds a small centerpiece, and vintage skis are mounted on the wall above the seating.
Home in Wilmington
4.87 out of 5 average rating, 126 reviews

MtSnow* HotTub* Pool * AirHockey* PingPong * Darts

Welcome to our ❄newly listed❄lodge style home! HOT TUB✅ Our home is located on private 2.6 acre lot with beautiful views of Mount Snow in the distance. Our home offers easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our home. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in southern Vermont!

Guest favourite
Condo in Dover
4.92 out of 5 average rating, 123 reviews

Base of M.S. All Seasons Fun. Deck/HotT/Pool/Sauna

Sunsil Loft @ MountSnow, your ideal Getaway. Walk to the Base. Unbeatable access to skiing, hiking, biking. Vermont never stops to surprise you with its outdoor adventures, great food and views. The loft offers a cozy gas fireplace, private deck. The kitchen has all you need to prep meals. You also have access to the pool (Summer), sauna, hot tub and GYM. Whether you’re skiing, hiking and biking in summer, or enjoying the fall foliage, our loft is your perfect home base in the Green Mountains.

Guest favourite
A cozy fire pit is surrounded by stone, situated in the foreground of a spacious lawn. In the background, a modern chalet features large windows and a combination of wood and stone siding, framed by colorful autumn foliage.
Home in Winhall
4.95 out of 5 average rating, 168 reviews

Summit View Ski and Golf Retreat w/hot tub & Sauna

Summit View Chalet @ Stratton is the ideal VT retreat, Minutes from Manchester, directly across the entrance from Stratton's 27 Hole Championship Golf Course. Beautifully remodeled! Relax in the hot tub on the deck with direct summit views in any season. Enjoy shuttle access to lifts, minutes from snowmobiling, hiking, fine dining and shopping. Comfortable accommodations for 6 adults and 5 children. Perfect for 2 families to enjoy any season in Southern Vermont's beautiful Green Mountains!

Guest favourite
Home in Dover
4.92 out of 5 average rating, 93 reviews

FULLY renovated 1 bed/1 bath ski in-out condo!

Can't get closer to on the slopes than skiing to your door! Walk 100 ft. to the lift, ski locker at entrance. Nothing untouched, FULLY RENOVATED AND STOCKED 1 bd/1 ba unit w QN bed and QN sleeper sofa. Large closet with sheets, pillows, blankets, towels. Bath w/ soaking tub! Full size washer and dryer. Kitchen stocked with appliances, coffee maker, pots, pans, spices, paper products everything you need to cook! Wood burning fireplace, LARGE TV. All new furniture. Office and dining room.

Top Guest favourite
A quaint cabin emerges from a snowy landscape, with a red-trimmed exterior contrasting against the white snow. The roof is blanketed with fresh snow, and leafless trees surround the property, creating a peaceful winter scene.
Cabin in Peru
4.83 out of 5 average rating, 111 reviews

The Grateful Barn

THE GRATEFUL BARN IS BACK ! Renovated 1800's Vermont barn. Located on a National Forest Rd. & land locked by the entire Green National Forest. The Grateful Barn is a cozy converted barn located next to a seasonal country home. The Barn offers a private bedroom with a queen sized bed, 2 single beds in a loft area & a pull out double bed in living room. This remote VT location is just a few steps from the Long Trail …7 minute drive to Bromley & 20 minutes to Stratton or Magic MT.

Guest favourite
An aerial view showcases Ober Tal condo nestled among snowy landscapes, with the nearby Tamarack Lift visible along a snow-covered path. The surrounding area features trees and gently sloping hills, indicating a winter setting conducive to skiing and outdoor activities.
Condo in Stratton
5 out of 5 average rating, 27 reviews

Walk to Lift - 2 Bedroom Condo - Newly Renovated

Renovated 2 bedroom condo at Ober Tal. Walk to Tamarack Lift; Easy walk to Stratton village. Master bedroom has 1 queen bed. 2nd bedroom has a full bed over twin bunk bed. Pull out sofa bed in living room. It is steps away from Stratton's Tamarack lift. When there is snow coverage on the walkways, you can ski to and from the lift. Easily accessible parking. New for 2025-26: Brand new & quieter washer/dryer New toaster-oven Black-out blinds and curtains in master bedroom.

Guest favourite
Condo in Dover
4.93 out of 5 average rating, 108 reviews

MountSnow ski on/off condo in Vermont

Ski seasons just began Pool and Sports Center is open. Hours vary by day BBQ available for use by the outdoor pool pavilion On Mount Snow, Across from the Tin Lizzy trail leading to the Sundance Base Lodge and access to the Seasons Pass trail leading back to the condo. Very unique Condo in seasons as it has high vaulted ceilings. Condo is a 2 bedroom, 2 bathroom with 2nd bedroom on 2nd floor. Plenty of tennis and pickleball courts Best parking on the mountain

Top Guest favourite
A living room features a large stone fireplace with a wood storage basket beside it. A comfortable sofa with decorative pillows faces a wooden coffee table. Natural light floods the space through a large window, complemented by a nearby area rug.
Condo in Dover
4.87 out of 5 average rating, 255 reviews

Mt Snow Ski In/Out at Seasons

Directly on the mountain. Minutes walk to 2 trails. Full kitchen, dishwater, washer/dryer, microwave. Fireplace with free wood. Large screen TV in living room and tv in each bedroom. Plenty of board games. King size bed in Master. Free parking for 2 cars. Ground floor with deck with tables and chairs for relaxing. Free parking. The pool (indoor & outdoor) and hot tubs are free to renters as is fully equipped gym (all year) and tennis courts in summer.

Guest favourite
A cozy living area is designed with a comfortable sofa adorned with patterned cushions. A wood coffee table occupies the center, complemented by a lamp on each side. Natural light floods the space through large windows and a door leads to a balcony.
Condo in Dover
4.88 out of 5 average rating, 91 reviews

Cute, Cozy Condo at the base of Mount Snow

Cute, cozy condo located right at the base of the new Carinthia Base Lodge at Mount Snow. Enjoy the convenience of the Grommet Trail and the Magic Carpet access lift just steps away or the Nitro Lift located in the back. Our bright, open floor plan condo has views of the mountain. Full kitchen, fireplace, wifi. Ideal for a family of 4 or two couples. This is our second home and we are interested in working with people who will respect our property.

Guest favourite
An open living area features a large wooden dining table surrounded by metal chairs. The kitchen showcases modern appliances and a sleek countertop, while a comfortable seating area is arranged nearby with a sectional couch and coffee table against a textured wall.
Condo in Stratton
4.96 out of 5 average rating, 113 reviews

Luxury Stratton condo just steps to the lift!

Enjoy this beautifully renovated 1 bed/1 bath condo with a live fireplace conveniently located steps from the mountain and Stratton Village! The Tamarack chair lift is only a few hundred yards away! Washer and dryer in unit to warm up your wet clothes after a long day of skiing or mountain biking. Fully stocked kitchen, 50’ TV w/ AppleTV, cable, Amazon Alexa, 5G WiFi, Firewood and more! This is one of the nicest Ober Tal condos available for rent!

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