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

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

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

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Superhost
A charming treehouse sits elevated on wooden stilts, surrounded by lush greenery. Soft lighting decorates the deck area, creating a warm environment. A gravel path leads to the entrance, while the tranquil pond reflects the evening sky in the background.
Home in South Londonderry
4.84 out of 5 average rating, 172 reviews

Lovers Honey Pond Treehouse with hot tub & sauna

Guest Favorite VERY romantic abode…The Honey Pond Treehouse is made for you and yours! It’s constructed of all natural materials, has breathtaking views, and is outfitted with absolutely everything you need! Lifted high over a stocked trout pond way up in the birch trees…Enjoy private hot tubbing, sauna time, swimming & hammock time. Skylight was designed for stargazing in bed!! Just minutes to the slopes or enjoy our own groomed trails for Xcountry & snowshoes & nature walks!! High speed WiFi 🐣

Guest favourite
Condo in Dover
4.89 out of 5 average rating, 111 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!

Guest favourite
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.
Condo in Peru
4.99 out of 5 average rating, 83 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!

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
4.86 out of 5 average rating, 117 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
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.
Condo in Dover
4.91 out of 5 average rating, 114 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 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, 46 reviews

Ski In/Out, Cozy 3BR 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 ski trips with close friends. Tasteful furnishings, wood burning fireplace (free wood) and lift and mountain views from the deck and living room await your stay here. Comfortably sleeps 7, but can fit 8. "Single" bed in king bedroom is a sleeper chair, appropriate for a child or small adult.

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
4.94 out of 5 average rating, 157 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 favourite
The exterior of a multi-story grey building is shown, featuring a sloped roof and several square windows. A ramp leads to the main entrance, which is adorned with light fixtures and framed by greenery, including bushes and grass.
Condo in Londonderry
4.96 out of 5 average rating, 72 reviews

Magical Ski-In/Ski-Out Condo at Magic w/ game room

Relax trailside at Magic Mountain in a 1 bedroom, 1 bathroom ski in/ski out condo. Best suited for 4-5 guests with a queen size bed and a bunk bed. We have a massive couch if you add a few more. Great proximity to Bromley, Stratton, Okemo and Viking Nordic Center. The condo has a game room area just down the hall. On the lower level you have access to a locker room to store your skis etc. and a very small fitness area. Outside find picnic tables and fire pits all overlooking the mountain.

Guest favourite
Home in Dover
4.92 out of 5 average rating, 85 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.

Guest favourite
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.
Condo in Dover
4.92 out of 5 average rating, 105 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 Best parking on the mountain

Superhost
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.
Condo in Dover
4.75 out of 5 average rating, 12 reviews

Mount Snow direct access! Pool & hot tub! Ski

This ski condo offers stunning mountain views from your private deck, the perfect spot to unwind after a day on the slopes. Sleeping up to four, it’s ideal for small families or a friends' getaway. Inside, enjoy a fully equipped kitchen and a cozy living space for ultimate comfort. Community amenities include a hot tub, sauna, gym, tennis court and seasonal outdoor pool. Free WiFi and parking make your stay seamless. Relax and recharge in this perfect mountain retreat.

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, 243 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.

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