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Ski-in/Ski-out vacation 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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Top guest favorite

5 out of 5 average rating, 62 reviews

Four Seasons Slope-side Getaway at Mount Snow

Come stay at our lovely slopeside condominium at seasons of Mount Snow where you’ll be staying in spacious one bedroom unit with a comfortable king size bed and a wonderful pull out couch that comfortably sleeps 4. In winter we are right on the mountain giving you a true ski in ski out. In summer the rivers the mountain and hiking is right out our back door as we enjoy mountain biking hiking golfing and relaxing around the mountain environment. Our unit is well equipped for a wonderful vacation

The exterior of The Grateful Barn features a welcoming entrance with a porch and bright red trim. An American flag and a decorative flag hang next to the door. Lush green grass surrounds the area, contributing to a serene outdoor setting.

4.8 out of 5 average rating, 97 reviews

The Grateful Barn

THE GRATEFUL BARN IS BACK! Renovated 1800's Vermont guest barn. Located on National Forest RD & land locked by the Green National Forest. The Grateful Barn is a guest cabin located next to a seasonal country home. The Grateful Barn offers a private bedroom with a queen sized bed, 2 single beds in the music loft and a pull out double bed in living room. Recently remodeled bathroom with walk in shower. This remote VT location is a few steps from the Long Trail & 7 minute drive to Bromley Mountain

Top guest favorite

A winter scene is captured at sunset, with silhouettes of trees framing a vibrant orange and pink sky. A blanket of snow covers the ground, reflecting the warm hues, while the distant hills are lightly outlined by the fading light.

4.99 out of 5 average rating, 82 reviews

The ultimate ski in/ski out condo

Not only is my condo the definition of a ski in ski out, it’s the combination of wide open views, sunrises glistening over untouched fresh powder or perfectly manicured corduroy beckoning you to the first run to the first lift each morning that makes it a skiers dream. No stairs, no pushing or shushing, simply buckle in on the couch, slide the door, click in skis, point down the hill and go! Ski back with equal ease for a beer, lunch or a zoom call. Skiing at its most civilized and effortless!

A comfortable living area features a gray sofa paired with a stylish floor lamp. Mounted on the wall are two crossed red skis, adding a mountain-themed touch. Soft lighting from twinkling fairy lights above creates a relaxing ambiance in the space.

Home in Wilmington

4.86 out of 5 average rating, 114 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!

A cozy seating area features two woven chairs adorned with striped cushions. A small table holds a decorative vase with flowers, set against large windows that frame a vibrant backdrop of autumn foliage outside.

4.91 out of 5 average rating, 113 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.

Top guest favorite

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, 152 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!

Top guest favorite

A spacious living area is introduced, featuring a stone fireplace and a large sectional sofa arranged around a coffee table. A dining table and chairs are positioned nearby, with natural light filtering through large windows adorned with curtains.

4.94 out of 5 average rating, 71 reviews

Condo w/ great amenities 4-seasons! Ski in Ski out

True ski in ski out ground floor condo w/ private entrance. Wood burning fireplace, wood included! King size bed in master, true Queen murphy bed, 1-memory foam cot, plus air mattress. Fully stocked & functional kitchen, including Keurig & Mr. coffee. Full bath w/blow dryer. Seating; kitchen counter, expandable table, wine barrel bar top. Walk out the door & down the steps to the NEW Sundance high speed lift. Take the Seasons trail home. Brand new state of the art Sports Center included.

Top guest favorite

A charming front porch is displayed with seating arrangements that include a cozy sofa. The white exterior is complemented by wooden beams and decorative lights, while seasonal decorations, like corn stalks, add character. A vibrant landscape frames the home.

Home in Wilmington

5 out of 5 average rating, 34 reviews

Rustic home near skiing & lakes, walk to downtown

This updated home exhibits rustic charm while also being situated in the perfect location. Spend time with friends and family in this 5 bd, 2 bath home that boasts a large kitchen / dinning room for entertaining. Enjoy the nearby skiing, lakes, hiking within a few miles. Walking distance to downtown where you will be enamored by the many restaurants, bars, breweries, and shops. There is also a one of a kind gameroom with enough room for all! Come experience Vermont the way it should be.

The kitchen features modern cabinetry with a combination of dark and light finishes. A farmhouse sink is positioned beneath a window, complementing stainless steel appliances, including a gas range and dishwasher. A spacious countertop offers ample preparation area.

4.91 out of 5 average rating, 82 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.

A cozy dining area is highlighted by a round wooden table surrounded by black chairs. The open living room features a comfortable sofa and a decorative area rug. Soft lighting is provided by a stylish chandelier, enhancing the homey atmosphere.

Condo in Stratton

4.94 out of 5 average rating, 174 reviews

Updated Ski in/Ski out Stratton Condo!

Enjoy our cozy ski-in ski -out condo in the Ober Tal complex at Stratton. This newly renovated condo offers a warm, welcoming stay with modern farm house charm! Located just above the base of the mountain, our condo is a stones throw from the nearest lift ( 200 ft) and a ski lovers dream. Unwind after a long day of skiing/snowboarding or take convenient 5 minute stroll to the Village for a bite to eat or some shopping. *Mountain biking & concerts offered in the summer season.*

A stone fireplace, featuring a wooden mantel adorned with items, is complemented by a modern television mounted above. The room is painted in a warm yellow hue, while fireside logs are neatly stacked in an iron holder to the side.

4.92 out of 5 average rating, 104 reviews

Seasons at Mount Snow ski on/off condo in Vermont

Pool and Sports Center is open. Hours vary by day BBQ available for use by the outdoor pool pavilion WiFi upgrade to fiber optics 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 Beautiful fall foliage

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.

4.87 out of 5 average rating, 242 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.

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

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

Free parking on premises

Air conditioning

Ski-in/ski-out house rentals

An entertainment area featuring a billiard table and foosball table welcomes guests to enjoy recreational activities. Large windows allow natural light to illuminate the space, while flat-screen TVs are mounted on the walls. A cozy seating area is set for relaxation, surrounded by wooden railings.

Home in Jamaica

4.88 out of 5 average rating, 25 reviews

The Mountain Escape

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.

4.89 out of 5 average rating, 19 reviews

Private chalet | hot tub, shuttle & ski home trail

Home in Stratton

New place to stay

Stratton Ski In/Ski Out Trailside 4 Bedroom Condo

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

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, 28 reviews

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

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.

Home in Landgrove

5 out of 5 average rating, 24 reviews

Landgrove Charm - Post and Beam Barn House

Top guest favorite

The spacious living room features a large, sectional grey couch and a white armchair, arranged around a wooden coffee table. A brick wood-burning fireplace is situated against a wooden wall, with a mounted TV above it. The room is illuminated by warm lighting.

4.98 out of 5 average rating, 58 reviews

Winter Skiing @ Mt Snow! Ski off trail sleeps 8.

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

The living area features a yellow sectional sofa arranged invitingly around a coffee table. Natural light fills the room through large windows, complemented by a decorative mirror. A dining table is positioned nearby, with a cozy fireplace providing warmth and ambiance.

4.87 out of 5 average rating, 23 reviews

Cozy 2BR Condo Walking Distance to Mount Snow

A snow-covered path leads to a two-story home nestled among trees. The exterior features large windows and a welcoming balcony. Snow blankets the ground, with a ski trail visible in the background, creating easy access to the slopes.

Townhouse in Stratton

4.77 out of 5 average rating, 48 reviews

Ski In / Ski Out 4BR / 3BA Private Hot Tub and sha

A wooden dining table is set for a meal, surrounded by several wooden chairs. A spiral staircase leads to the upper level. Ski equipment is mounted on the wall, and a comfortable seating area is visible in the background, with a relaxed atmosphere created by soft furnishings.

Townhouse in Peru

4.69 out of 5 average rating, 26 reviews

The Best Vermont Has to Offer!

A cozy living room is highlighted by a comfortable sectional sofa facing a modern fireplace, adorned with seasonal greenery. A large mirror reflects natural light from the windows, and a television hangs above a wooden media console, completing the inviting ambiance.

4.97 out of 5 average rating, 30 reviews

Mt Snow Condo, 4-min Walk to Sundance Dog Friendly

A spacious living area features high wooden walls and large windows allowing natural light. Two sofas are arranged around a wooden coffee table, and a dining table is visible in the background. A Christmas tree adds a festive touch to the corner of the room.

Chalet in Dover

4.65 out of 5 average rating, 34 reviews

Mount Snow Chalet w/ Ski-Home Trail & Indoor Sauna

A spacious living area features a rich brown leather sofa paired with light-toned armchairs. A wooden coffee table complements the decor. Above, a loft area overlooks the space, with a staircase leading to it. Natural light fills the room through nearby windows.

Chalet in Dover

4.84 out of 5 average rating, 189 reviews

4BD 2BA | Mount Snow VT | Ski-Back Trail | Shuttle

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, 147 reviews

Stone's Camp on Stamford Stream

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.

4.7 out of 5 average rating, 10 reviews

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

Ski-in/ski-out condo rentals

A circular outdoor pool is surrounded by a landscaped area, featuring several trees and bushes. The building's large glass entrances reflect natural light. Sun loungers are positioned nearby, and a set of steps leads from the pool to the patio area.

Condo in Stratton

4.97 out of 5 average rating, 65 reviews

Stratton Mt Summer: Golf, tennis, hike, bike, swim

A snow-covered slope is showcased, featuring fresh corduroy tracks that create a textured pattern across the landscape. In the distance, a glowing sunrise illuminates the horizon, casting a warm light over the snowy terrain and trees, enhancing the serene atmosphere.

4.97 out of 5 average rating, 89 reviews

Cozy Mountain Condo - Ski In/Ski Out

A cozy living area is highlighted by a stone fireplace, featuring firewood neatly stacked beside it. A flat-screen TV is mounted above the mantel, with built-in cabinets on either side. A sectional sofa and wooden coffee table provide comfortable seating for relaxation.

5 out of 5 average rating, 24 reviews

Slopes N Seasons | Trailside Condo at Mount Snow

A cozy living area features a large sectional sofa and a wooden coffee table, set on a spacious area rug. Natural light filters through a large window, with a stone fireplace and a mounted television providing warmth and entertainment.

4.96 out of 5 average rating, 46 reviews

Cozy Fall Retreat: 2BR w/Pool, Fireplace & Arcade

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, 43 reviews

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

The exterior of the lodge features a blend of stone and wood elements, with multiple balconies and large windows reflecting the surrounding landscape. The entrance is framed by a welcoming staircase, leading to the main doorway marked with a sign that reads 'Hardwood Lodge'.

Condo in Stratton

4.92 out of 5 average rating, 38 reviews

Perfect 3 Br. Getaway Condo in Stratton, Vermont!

Condo in Stratton

5 out of 5 average rating, 12 reviews

Luxury Condo * 2 Ensuites * Fall Foliage

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, 23 reviews

Walk to Lift - 2 Bedroom Condo - Newly Renovated

Destinations to explore