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Ski-in/Ski-out vacation rentals in Connecticut River

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Top-rated ski-in/ski-out rentals in Connecticut River

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

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Top guest favorite

A vibrant red sectional sofa features colorful throw pillows, providing comfortable seating. A rustic wooden coffee table sits in front, resting on a patterned area rug. Natural light filters through large windows adorned with light curtains, illuminating the cozy living area.

Condo in Carrabassett Valley

4.97 out of 5 average rating, 67 reviews

2BR, 2BA Sugarloaf Mountain Ski-in Ski-out condo

Second-level Sugarloaf Mountain condo getaway! Master bedroom w/ queen bed; upper level open loft bedroom sleeps up to 4 in 1 twin-sized bunk beds + 2 twins; 2 full baths; gas-fireplace; laundry; granite kitchen countertops; & private balcony. Extremely convenient 1-min walk to Snubber chairlift, 30-sec walk to shuttle stop, & easy trail access to Sugarloaf Outdoor Center. Year-round activities: alpine skiing, x-country skiing, snow shoeing, fat biking, mountain biking, golf, hiking, & more!

A spacious mudroom is featured, lined with warm wooden paneling. Ski equipment is organized on the wall, complemented by hooks for jackets. A sturdy wooden bench provides seating, while a striped rug adds a touch of color. Firewood is neatly arranged nearby for convenience.

Home in Carrabassett Valley

5 out of 5 average rating, 16 reviews

Mountainside - Ski In/Out Condo

You'll be close to everything in this modern condo. Top of Mountainside Road - walk 1 min to the trail & ski down to Whiffletree lift. Easy to stop for lunch or quick warm up. Après - stroll down to the Village for food & fun! 3 bedrooms (2 queen beds & 4 bunks) Open Kitchen, living & dining room w/ fireplace. Large mudroom for all your gear. Deck overlooking Bigelow Range. Last 6+ years 4.9 star reviews & managed by rental agent. Now Book direct with owner, a Sugarloafer since 1977!

The exterior of the cabin is illuminated in soft evening light, highlighting its wooden structure and stacked stone foundation. A covered porch with rustic wooden beams provides an entryway, while trees frame the backdrop, creating a natural setting.

Apartment in Bridgton

5 out of 5 average rating, 17 reviews

Lil’ Ski Chalet-Private Assoc. Beach! 1 dog OK!

This unique "Arched Cabin" is located on the side of Pleasant Ski Mtn off of Rabbit Run Trail. Summer Private Association beach access! Creatively built with local hewn pine boards and radiant heated flooring, this Lil' Chalet has been designed with a spirited and eclectic ski theme through out. Only steps from Bridgton's best skiing and hiking, this 1st floor walk out is 30 min to N Conway eats/ski/shopping and 7 min to the sweet village of Bridgton. Local favs/Association Beach access😎

A snow-covered landscape features a modern condo complex with multiple floors and balconies. Skiers are seen gliding down the slope in the foreground, while the mountainous backdrop adds to the winter atmosphere.

Condo in Stratton

4.94 out of 5 average rating, 170 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.*

The living and dining area features a spacious wooden table surrounded by classic chairs, complemented by a large mirror reflecting natural light. The room is adorned with green walls and a high vaulted ceiling, while a comfortable seating area includes a sofa and armchairs flanking a fireplace.

Condo in Ludlow

4.8 out of 5 average rating, 185 reviews

Okemo Mountain Getaway for Families w/ Pool Access

Perched on Okemo mountain, this spacious condo is the perfect year-round escape for families and groups. With ski-in/ski-out access, a cozy wood-burning fireplace, and a private balcony, it's perfect for any season—whether you're carving the slopes, hiking scenic trails, or enjoying the vibrant fall colors. Take a dip in the seasonal shared pool or unwind in the hot tub. Featuring a fully equipped kitchen, BBQ grill, and all the comforts of home, it's the ideal mountain getaway!

Condo in Carrabassett Valley

4.93 out of 5 average rating, 46 reviews

Post & Beam, Ski-in/Ski-Out Birchwood Penthouse

Editors choice!! Located in the heart of the action!! Beautiful post and beam, ski-in/ski-out Birchwood penthouse perfect for a family and friends getaway. Sleeps 10. Fantastic views of the mountain as well as the Bigelow range. Minutes walk (or ski) to the best that Sugarloaf has to offer: Sugarloaf Village, Upper Snubber trail and lifts (Sawduster), Shipyard Brew Haus, Sugartree Sports & Fitness Center with indoor pool, indoor and outdoor hot tubs, steam room, sauna and more!

A living area showcases a green sofa paired with two distinct chairs, one featuring a yellow accent. A glass coffee table rests on a cowhide rug, and several framed artworks adorn the walls. Natural light floods the space through sliding glass doors that open to a balcony.

Condo in Warren

5 out of 5 average rating, 24 reviews

Sugarbush ski in/out condo with seasonal pool

Enjoy this ski-on/ski-off, stylishly renovated mountainside condo; literally steps to the ski-on/off trail. The space is perfect for guests who enjoy uber-convenient access to the slopes and great aprés ski options, including the famous Chez Henri Bistrot. Take advantage of our heated pool for guests during the summer months. There are stunning mountain views from the living room and private balcony. Mountainside Ski Service is right downstairs for those last minute tune-ups.

A dining area is featured with a wooden table set for six, complemented by dark blue napkins. A stone fireplace serves as a warm backdrop, while a vibrant wall art depicting trees adds a touch of color. Natural light enhances the inviting atmosphere.

Condo in Killington

4.95 out of 5 average rating, 105 reviews

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

Ski On-Ski Off!! Beautiful remodeled condo is in the heart of Sunrise at Bear Mountain. The designer kitchen features granite counter tops and top of the line stainless steel appliances. The main focal point in the living room is a massive stacked stone fireplace with a flat screen on the mantel. Recent upgrades include new living room furniture, master bed room furniture & updated tile in both showers. Additionally I own the adjoining unit & if you want more info see below

The exterior of a two-story condo is surrounded by snow, showcasing a sloped roof and a welcoming red door. Bare trees provide a natural backdrop, with a glimpse of the mountain visible in the distance. Soft snow blankets the ground, creating a serene atmosphere.

Apartment in Jay

5 out of 5 average rating, 7 reviews

Absolute best ski on/off at Jay.

Location, location, location. This 2br Slopeside condo is position A on the snowiest mountain in the east. Inside, you'll find 2 bedrooms featuring a queen bed and a twin over full bunk. The kitchen comes fully equipped to make meal prep a breeze. The cozy living room has a gas fireplace to warm up or relax and enjoy an après drink. Our condos always feature complete linens, towels, and essential sundries because no one wants to lug that stuff to their vacation.

A ski locker room is displayed with several individual lockers arranged along the walls. Each locker is labeled with a number. A set of ski equipment rests against the wall, while the floor features a textured tile surface.

Condo in Carrabassett Valley

4.85 out of 5 average rating, 33 reviews

Pet friendly condo - come visit for the summer!

This centrally-located condo offers proximity to various amenities. Ski in-Ski Out, Equipped with a full kitchen, bathroom, flat-screen TV, ski locker, Wi-Fi, and more, this condo ensures a comfortable stay. Step outside to find the ski lift conveniently located just outside the door. Suitable for 2 adults, guests can enjoy post-skiing drinks at the Sugarloaf BrewHaus within walking distance or the Sugarloaf Fitness Center across the street (for a fee). Dog friendly!

A skier in a bright yellow jacket navigates through deep snow, creating a cloud of powder. Snow-covered trees line the slope, and the cloudy sky can be seen in the background, highlighting the winter atmosphere.

4.9 out of 5 average rating, 49 reviews

True Ski-in Ski-out! Walk to hotel-waterpark-golf

This is the perfect mountain spot all-year-round! “The Shredquarters” is a true ski-in-ski out condo with a fully fitted kitchen, new furniture throughout, free Wi-Fi, in unit dryer and washer, a WFH desk setup, and more! Easy access to all, it’s a three minute walk to the hotel restaurants, spa, and pump house water park and ice rink, and a 7 min walk/2 min shuttle to the golf course. There is A/C for the summer and a cozy gas fireplace in the winter.

A welcoming entryway features tile flooring and wooden accents. A bench is positioned near a sliding glass door that provides access to the outdoor area, which is framed by a tree and visible greenery. Storage solutions include coat hooks and a wooden rack.

Vacation home in Carrabassett Valley

4.93 out of 5 average rating, 44 reviews

Ski-in, Ski-out Timbers 4-Bedroom condo

This Timbers location cannot be beat: ski-in, ski-out, only a 5 minute walk to base village and right next to the Superquad! Newly furnished and stylishly decorated, this family-friendly 4 bed, 3 bath Timbers condo features an open-concept main floor with living area, kitchen, and dining table for 10. Well-stocked kitchen and TV for each bedroom. Upstairs has 3 BR, 2 BA and basement has ski prep & rec area, additional bathroom and bunk room.

Vacation rentals for every style

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Chalets

Adventure-ready homes with après-ski style

Apartments

Convenient locations with everyday essentials

Villas

Luxurious estates for the ultimate escape

Popular amenities for Connecticut River ski-in/ski-out rentals

Free parking on premises

Air conditioning

Ski-in/ski-out house rentals

The image shows a cozy red house nestled among snowy trees, positioned alongside a freshly groomed ski slope. The surrounding landscape features a backdrop of tall trees and a cloudy sky, emphasizing the winter setting within a serene mountain environment.

Home in Bartlett

4.82 out of 5 average rating, 72 reviews

The Mountain House

A large house featuring a blend of stone and timber architecture is set against a backdrop of lush greenery. The exterior showcases a prominent gable roof, large windows, and a welcoming porch. A separate structure with a barn-like design is visible in the background.

4.97 out of 5 average rating, 120 reviews

Cozy Mountain Home w/Million $ View

A spacious bed is dressed in a quilt featuring soft pastel colors and patterns. Two pillows rest at the head, with a patterned throw blanket draped across the bed. In the background, a partially visible bathroom is seen through an open doorway.

4.92 out of 5 average rating, 206 reviews

Beautiful guesthouse -perfect for long stays

4.98 out of 5 average rating, 159 reviews

Spacious Eco-Friendly Stowe Home for Family Fun

Top guest favorite

Home in Killington

4.99 out of 5 average rating, 145 reviews

DoubleDen - AC, Hot Tub, Game Room, Fire Pit

A spacious living area is highlighted by tall windows that offer a panoramic view of the surrounding landscape. Light wooden beams adorn the ceiling, while light-colored sofas and a central coffee table create a comfortable seating arrangement. A cozy rug lies on the floor, adding warmth to the space.

Home in Winhall

4.95 out of 5 average rating, 137 reviews

Summit View Ski and Golf Retreat w/hot tub & Sauna

A quaint, modern condo is shown amidst a winter landscape, surrounded by snow-covered trees. A wooden deck is visible at the front, complemented by large windows that allow natural light to enter, creating a connection between indoor comfort and outdoor scenery.

4.82 out of 5 average rating, 117 reviews

Charming Sugarbush Standalone Condo

Top guest favorite

The exterior of the ski condo showcases a charming mountain design, with a steeply pitched roof and large front windows. Snow covers the landscape, and a set of wooden steps leads to the entrance, flanked by gently sloping snowdrifts.

4.95 out of 5 average rating, 20 reviews

Large 4BR/4BA Ski In/Out Village Chair at Jay Peak

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

A green, grassy area is framed by tall, slender trees. Two benches are positioned on either side, offering a place to sit and admire the expansive view of distant hills and valleys under an overcast sky.

Apartment in Chester

4.89 out of 5 average rating, 501 reviews

Beautiful 2 Bedrooms in Mountains w/ full kitchen

A snow-covered slope is visible, with two skiers navigating down the trail. Towering pine trees line the sides, with a distant view of mountains capped with snow under a clear blue sky.

Chalet in Bartlett

4.77 out of 5 average rating, 118 reviews

Ski-In/Ski-Out Attitash! Base of Abenaki Quad!

A one-story cabin is partially enveloped by a blanket of snow, featuring a covered porch with orange railings. The entrance is accessible via a gentle ramp, while trees in the background provide a natural setting. Soft evening light gently illuminates the cabin.

Apartment in Ludlow

4.92 out of 5 average rating, 279 reviews

Okemo Vermont Getaway

A wooden cabin exterior is surrounded by snow-covered ground and tall trees. The porch features steps leading up to the entrance, and windows are visible on the facade, framed by the natural setting.

Chalet in Malone

4.88 out of 5 average rating, 105 reviews

The Ausable- Slopeside Ski Chalet

The exterior of the condominium showcases a three-story building featuring light brown wooden siding and a pitched roof. Snow covers the ground and roof, creating a winter ambience. A wooden deck with steps leads to the entrance, flanked by trees and a blue sky.

4.92 out of 5 average rating, 160 reviews

Ski in Ski out - fantastic location on the trail

A view from the ground floor unit showcases a lush, green lawn bordered by rocky outcrops. Sparse trees dot the landscape, with mountains rising in the background under a partly cloudy sky. The exterior of the neighboring building is visible to the right.

Condo in Killington

4.82 out of 5 average rating, 257 reviews

Ski, Ride, Walk On/Off Condo On Pico at Killington

Chalet in Killington

4.87 out of 5 average rating, 248 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

A ski lift is visible in the foreground, surrounded by snow-covered trees. In the background, a multi-level townhouse is seen, featuring a balcony and multiple peaks on its roof, illustrating a serene winter landscape.

4.87 out of 5 average rating, 249 reviews

Sunday River Locke Mountain Ski In/ Ski Out Pool

Ski-in/ski-out cabin rentals

A spacious log cabin is set amidst lush greenery, featuring a welcoming porch and multiple windows that allow natural light to fill the interior. The well-maintained lawn offers a peaceful atmosphere, with trees surrounding the property, enhancing the sense of seclusion.

Cabin in Mendon

4.85 out of 5 average rating, 249 reviews

THE CABIN....a Vermont log home

A wooden cabin is nestled among tall trees, featuring a spacious front deck with wooden railing. The sloping roof and large windows contribute to a welcoming exterior, framed by lush greenery and undergrowth. Sunlight filters through the trees, enhancing the serene woodland setting.

4.96 out of 5 average rating, 188 reviews

Honeymoon Cabin with Jacuzzi Tub

A cozy living room features wooden walls and a vaulted ceiling. Comfortable seating is arranged around a rustic stone fireplace. Large windows allow natural light to fill the space, while a TV is mounted on the wall for entertainment.

Cabin in Prattsville

4.91 out of 5 average rating, 234 reviews

Little Red Cabin Near Windham & Hunter w/ Hot Tub

The main living area features a round wooden dining table surrounded by four chairs. A comfortable sofa is positioned next to a cozy ottoman. Natural light enters through two large windows, offering views of the wooded surroundings. A floor lamp and a desk with a computer complete the space.

Cabin in Warren

4.93 out of 5 average rating, 404 reviews

Cabin in the Woods

The exterior of a two-bedroom cabin features warm wooden siding and a snow-covered ground. A single white door is visible, along with a small electrical box and a clear blue sky overhead. Surrounding trees and distant hills add to the serene mountain setting.

Cabin in Malone

4.85 out of 5 average rating, 156 reviews

The Sugar Bush (#2)

The cabin showcases a rustic wood exterior, with large windows reflecting the sky. Surrounding snow-covered terrain emphasizes its secluded location among trees, while a spacious deck provides outdoor seating. The roof's overhang suggests possibilities for enjoying winter views.

4.93 out of 5 average rating, 189 reviews

Silver Bear Cabin, 15 minutes from Whiteface!

The exterior of a cozy cabin is depicted, featuring a wooden facade with a steeply pitched roof. A bright yellow door welcomes guests, while two individuals stand on the front steps. Snow covers the ground, and trees cast shadows across the scene.

Cabin in North Creek

4.87 out of 5 average rating, 167 reviews

Adirondacks Garnet Hill: pristine lake, privacy

A charming cabin is set within a wooded landscape, surrounded by lush greenery. The dark exterior is complemented by green shutters and a small garden in front. A second structure is visible behind the cabin, with a porch that offers a casual outdoor space.

Cabin in Schuyler Falls

4.88 out of 5 average rating, 414 reviews

Cozy Cabin

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