Ski-in/Ski-out holiday 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

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, 103 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!

A tranquil lake reflects the vibrant colors of autumn foliage, showcasing a mix of red, orange, and yellow trees. A small island featuring a cluster of trees and shrubs emerges in the foreground, surrounded by calm waters and a gentle green grass shoreline.

5.0 out of 5 average rating, 73 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

4.87 out of 5 average rating, 140 reviews

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

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!

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.

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.

4.95 out of 5 average rating, 104 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.

5.0 out of 5 average rating, 8 reviews

Apartment in Dover

Peaceful Ski Escape in Mountain Village

Cozy 2BR/2BA condo with Mt. Snow views, just ½ mile from the lifts. Free MOOver shuttle outside. Sleeps 6 with two queen beds and a sleeper sofa. Relax by the fireplace after a day on the slopes. Includes Smart TV, fast Wi-Fi, full kitchen, linens and bath towels, ski locker, and laundry in building. Enjoy the indoor pool, new hot tubs, and infrared sauna. Ideal for ski trips and year-round mountain getaways. Perfect for ski weekends or relaxing stays with easy access to Mount Snow. No pets.

5.0 out of 5 average rating, 57 reviews

Home in Wilmington

Game Room, near skiing and lake, 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.

4.84 out of 5 average rating, 118 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.

5.0 out of 5 average rating, 15 reviews

Apartment in Stratton

Stratton walk on/off, walk to village, fireplace

This Obertal 1 bedroom 1 bathroom is PERFECT for your weekend and week long getaways to Stratton! After a long drive, park and unload your car and don't worry about her for the rest of your stay! With the mountain just steps away you can walk to skiing/riding, apres drinks, dinner, music, and shopping! • 1 bedroom (Queen) • 1 bathroom • 1 pullout sofa in the living room (Full/Queen) • Walk on/off skiing/riding • Walk to Village (food, drink, shops) • Fireplace

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, 261 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.