Ski-in/Ski-out vacation rentals in Winhall

4.9 out of 5 average rating, 183 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

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, 144 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!

4.92 out of 5 average rating, 128 reviews

Base of M.S. All Seasons Fun. Deck/HotT/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 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 @ Seasons on Mount Snow (Ski-In/Out)

⌲ Escape to Seasons on Mount Snow & stay in our fully equipped 3 bedroom condo where you can you can ski-in & out directly from the condo building! ⌲ Enjoy the log burning fire (wood provided), smart TV & boardgames plus the fabulous Seasons on Mount Snow facilities which include a gym, pool, hot tub, sauna & fire pit. ⌲ Spring thru fall activities in the area include hiking, biking, tennis & pickleball (at Seasons), scenic rides, lakes, golf, camp, spa & enjoying the stunning fall colors.

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, 107 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, 135 reviews

A mid-century modern home set among lush greenery features a stone foundation and large windows. A brick chimney rises above the roofline, while several wooden Adirondack chairs are positioned on a stone patio, providing a relaxing outdoor space to enjoy the surrounding nature.

Home in Cavendish

Midcentury Hillside Retreat - Summer Paradise

Enjoy this peaceful retreat in the heart of the Green Mtns and surrounded by 130+ acres of private woodland. Dramatic field stone fireplace and spectacular panoramic views of Mt Ascutney into New Hampshire from the entire living space. Large chef's kitchen. Private master suite and two guest bedrooms. The perfect get-away for relaxing with family and friends. Exceptional hiking, biking and Connecticut River adventures. Near GMHA and Woodstock. Great restaurants, fun village shopping nearby.

5.0 out of 5 average rating, 27 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!

4.83 out of 5 average rating, 120 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.

4.9 out of 5 average rating, 241 reviews

A pathway lined with lush greenery leads to a bungalow with a screened-in porch, featuring outdoor seating. The soft sunlight filters through the foliage, creating a serene entrance to the welcoming space.

Home in Williamstown

Hollywood Bungalow in the Berkshires #C0191633410

Cool Cozy Rustic Country Bungalow with 7.1 Screening Room on filmmakers/artists' enclave that's well-located in clean and beautiful Williamstown, near incredible Hiking Trails, Farms, Skiing, MASS MoCA, Clark Art Institute, Williams College, with Pool access, Smart TV, Porch and Patio, Grill, Fire Pit, Piano Bar Outbuilding with stereo & its own WIFI, First Floor Bathroom with Jacuzzi Bathtub, Laundry, fast WIFI, and lots of outlets in a quiet area on a quiet street.

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!

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. The pool (indoor & outdoor) and hot tubs are free to renters as is fully equipped gym (all year) and tennis courts in summer.