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

4.91 out of 5 average rating, 181 reviews

A spacious ski home is surrounded by snow-covered trees, featuring a modern design with a sloped metal roof. Large windows allow natural light to enter, while a gravel driveway leads to the entrance. This bustling wooded area provides a serene backdrop during winter.

Home in Peru

Beautiful Bromley/Manchester VT Retreat w/hot tub

"Manchester Moose!" Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester, Beautifully remodeled VT vacation getaway nestled in the Green Mountains. Closest skiing to quaint Manchester VT, minutes from snowmobiling, hiking, fine dining and shopping. This home features 5 bedrooms, 3 with queen beds including 2 Masters, and 2 bedrooms with double bunks. Perfect for 2 or 3 families to enjoy any season in Southern Vermont's beautiful Green Mountains! YouTube video link @GreenMountainStay

ValueFamilyComfort

A spacious living area is depicted with a large sectional sofa and a wooden coffee table. A stone fireplace serves as a focal point, featuring a mounted TV above. Natural light streams through the windows, illuminating bookshelves filled with games and books, while a stack of firewood is neatly arranged beside the fireplace.

4.92 out of 5 average rating, 105 reviews

Slopeside Condo @ Seasons on Mt Snow (Ski-In/Out)

Escape to the mountains & stay in our fully equipped 3 bedroom (ski in/out) condo. Enjoy the wood burning fire (wood provided), smart TV & boardgames as well as the fabulous Seasons on Mt Snow facilities where you can relax in a hot tub, pool or sauna. Our ski in/out location is the best on the mountain, between the main face & Carinthia Freestyle Park! See below for info on activities in the warmer months which include hiking, biking, scenic rides, lakes, golf, camp, a spa & the fall colors!

FamilyValueQuiet

4.98 out of 5 average rating, 58 reviews

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

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.

LocationFamilyBathroom

4.92 out of 5 average rating, 128 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.

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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

4.85 out of 5 average rating, 143 reviews

MtSnow HotTub Pool Table 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!

FamilyLocationQuiet

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, 106 reviews

Great Amenities-Season Condo gym-sport center-pool

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.

FamilyLocationParking

4.98 out of 5 average rating, 60 reviews

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

Farmhouse With Large Game Room, 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.

LocationFamilyHeating

5.0 out of 5 average rating, 26 reviews

A spacious living area features a rustic stone fireplace and a large, comfortable leather sofa arranged around a wooden coffee table. Large windows invite natural light, while a textured area rug adds warmth to the wooden flooring. Decorative elements include a chandelier and wall signage.

Home in Stratton

Stratton walk on/ski off, Kings, hot tub, shuttle

Perfect spot for year round relaxation! Located on Stratton Mountain this townhome has everything you could want. • 4 bedrooms • 4 full bathrooms (bathroom on every floor!) • Sleeps 10 across 7 beds (3 King and 2 sets of twin bunks) • 2 living areas • Hot tub • Shuttle • Walk to trails! ~400 yard walk • Ski nearly all the way home! ~50 yard walk • 5 min to Pikes Falls swimming hole • 18 min to Bromley • 25 min to Manchester PLEASE NOTE: Ski on/off is snow/weather dependent!

LocationFamilyGrill

4.84 out of 5 average rating, 119 reviews

Cabin in Peru

The Grateful Barn

THE GRATEFUL BARN is a SW Vermont classic. Renovated 1800's Vermont barn. Located on a National Forest Rd. & land locked by the entire Green National Forest The home 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 steps from the Long Trail, 7 minute drive to Bromley & 20 minutes to Stratton or Magic MT.

FamilyLocationGrill

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.

4.88 out of 5 average rating, 262 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.

FamilyLocationCheckout

4.97 out of 5 average rating, 120 reviews

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

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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