Ski-in/Ski-out vacation rentals in Carrabassett Valley

An inviting living room features a gas fireplace framed by wooden paneling. Two blue armchairs and a gray sofa, adorned with a checkered throw, are arranged around a wooden coffee table. A window seat with comfortable cushions overlooks the snowy exterior, with natural light brightening the space.

4.96 out of 5 average rating, 23 reviews

Snowflower Village Trailside Condo

Come enjoy a Sugarloaf getaway that is convenient for you and your family with our Ski- in/Ski- out Snowflower Court Trailside Condo, located off the Snowbrook trail and Snubber Chairlift. In the winter, enjoy hitting the slopes and a cozying up in the window seat where you can watch the snow falling down! Our 2 bedroom, 2 full bath Condo is pet friendly; the perfect location to rest and relax with the comforts of being central to some of the best four season activities this area has to offer.

LocationFamilyWalkability

A living area features a stone fireplace with a wooden mantel, overlooking expansive windows that provide mountain views. A large couch is positioned centrally, complemented by a coffee table. The space includes a flat-screen TV and a bar area with high stools, all set on wooden flooring.

4.92 out of 5 average rating, 48 reviews

Spacious 4 BR Condo in Carrabassett Valley

Looking for direct access to adventure? This is it! Space for 10 means 2 families easily fit. Trail access is just a few steps away, straight to the super quad. Want to start slower? Try the shuttle to the village! Need to unwind at the end of the day? Downstairs family room provides large couch, tv, games, puzzles, etc for the kids while the adults enjoy some quiet time in the upstairs kitchen/living room. Hot tub to ease muscles at the end of an adventurous day! *hot tub closed May-Oct*

LocationFamilySkiing

A cozy living area features a comfortable sofa and an accent chair beside a stylish table. A propane fireplace is framed by wooden shelves displaying decorative items. A flat-screen TV is positioned on a wooden console, with board games and books available for guest use.

4.97 out of 5 average rating, 124 reviews

Cozy Ski-In/Ski-Out Escape at Sugarloaf with AC

Cozy ski-in/ski-out condo in Sugarloaf’s desirable Sugartree complex. Wake up, click in, and ski out. Enjoy effortless slope access, mountain adventures, and relaxing après ski memories. Perfect for families, couples, and outdoor enthusiasts year-round, with hiking, mountain biking, golf, and foliage outside your door. Mountain views from your private balcony, plus indoor access to the pool, hot tubs & sauna at the Sugarloaf Fitness Center (add’l fees apply). Full kitchen, and AC for summer!

LocationValueParking

5 out of 5 average rating, 25 reviews

Gondola Village at Sugarloaf

Welcome to the heart of Carrabassett Valley in the western mountains of Maine. Come golf, hike, bike, ski, and relax. Conveniently located at the bottom of Whiffletree chair (ski in, ski out) with views of Bigelow. Take a scenic chairlift ride or test out the new Sugarloaf Bike Park. Sugarloaf Golf Club is only minutes away. Enjoy miles of mountain biking, hiking, and cross-country trails. Short walk to base area for restaurants and shops. Then relax in this cozy condo after your adventures.

FamilyLocationBiking

A living space features a modern fireplace framed by dark cabinetry. Two patterned armchairs are positioned around a wooden coffee table atop a plush area rug. A staircase leads to an upper level, while a well-equipped kitchen with wood cabinetry is visible in the background.

4.95 out of 5 average rating, 19 reviews

Ski-In Ski-Out Condo Perfect for Families!

Prime Location: Access the Condo Cross Cut trail right behind the condo, or take a leisurely 6-10 minute stroll to the Sawduster Chairlift and the popular Shipyard Brew Pub. Outdoor Space: Unwind on the porch after a thrilling day on the mountain. Fun for Everyone: Challenge your friends and family to a game of ping pong in the game area—perfect for friendly competition! Accommodations: Our 3 bedrooms and 3 bathrooms, plus a fun lower-level twin bunk bed, ideal for kids or extra guests.

FamilyLocationCleanliness

5 out of 5 average rating, 9 reviews

Modern Ski and Golf - West Mnt

New in 2021 4BR townhouse at Sugarloaf! Hot tub and pet friendly. Walk to the West Mnt Trail or hop the free shuttle to the base lodge. Features a master king suite, 2 queen bedrooms, full guest bath. Basement has a teen retreat including a queen bed and bunkbeds, a private bath, and living room. Two living areas with big smart TVs, mountain views, and a fully stocked kitchen. Steps from golf, hiking, and biking trails. Perfect for families or friends looking for year-round mountain fun!

LocationFamilyWalkability

A ski lift station is visible beside a designated area for skiers, surrounded by snow-covered terrain. The wooden structure features large windows and a steep roof. Nearby, lift chairs are lined up, ready for ascent, while skiers prepare at the base.

4.95 out of 5 average rating, 85 reviews

On-Piste, Ski-in/Ski-out Condo

*NEW LISTING* Book your stay at this ski-in ski-out, cozy studio condo centrally located at Sugarloaf USA. Upon arrival, no need to move your car! You will receive 2 parking passes, be steps from the Snubber Chair lift, settle your belongings in your personalized ski locker and walk a few minutes to the many shops and restaurants in the village. Warm up beside the electric fireplace between runs when you come in for lunch or a cup of coffee. Location, location, location! End unit condo!

ValueLocationIndoor spaces

4.98 out of 5 average rating, 142 reviews

A peaceful outdoor deck is showcased with two red Adirondack chairs facing a panoramic view of rolling hills and a clear blue sky adorned with clouds. Lush greenery surrounds the area, enhancing the natural setting.

Chalet in Sandy River

On-Mountain @ Saddleback-Hot Tub | Mountain Views

Welcome to the Last Chair Lodge - our family-friendly mountainside retreat at Saddleback Ski Area in Rangeley, ME. Custom, Maine-made Cedar Hot Tub! Incredible views - and sunsets - in all seasons. Ski-in/Ski-out in winter (natural snow dependent), in summer enjoy a peaceful, beautiful and comfortable mountain retreat. Come for outdoor adventures, time on the nearby lakes or just to unwind and soak in the scenery. One of very few mountainside listings with a hot tub, A/C and views!

FamilyLocationWifi

The kitchen features wooden cabinetry and a modern design with ample counter space. A stainless steel fridge and coffee maker are visible alongside a sleek electric stove. Four tan bar stools provide seating at the granite countertop, enhancing the functional layout.

4.94 out of 5 average rating, 49 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!

LocationValueBiking

A large, colorful sign reading 'SUGARLOAF' is positioned prominently among a cluster of rocks. Lush greenery and trees provide a natural backdrop, complementing the partly cloudy sky.

4.97 out of 5 average rating, 65 reviews

On Mountain Sugarloaf Condo

Welcome to your cozy, first-floor, pet-friendly condo at Sugartree! Adventure is right outside your door with ski in/ski out access to the slopes, biking & hiking trails all around, NEW downhill bike park, a world-class golf course, and breathtaking scenery. Central location with an on-site fitness center, pool, and hot tubs included for a fee (closed summer). Bars, restaurants, and shops within a short walk or ride. This is the ideal spot for creating new mountain memories!

LocationValueHospitality

4.96 out of 5 average rating, 111 reviews

First Tracks at Sugarloaf

Welcome to First Tracks! Located right on mountain bike trails and less than a three minute walk to Sugarloaf Village. With epic hiking, waterfall swims, disc golf, zip lining and mountain biking right out the back door we've got your vacation covered. Plenty of room to spread out in the condo with a game room downstairs and a hot tub to soothe your tired muscles after a day of play. Sugarloaf in the summer is magical. Let us know if you need any recommendations!

ValueLocationBeach

An open living area showcases a comfortable seating arrangement with gray sofas, complemented by a light coffee table. A dining table with wooden chairs is positioned near the well-equipped kitchen, featuring wooden cabinetry and modern appliances. Windows allow natural light to brighten the space.

4.87 out of 5 average rating, 45 reviews

Mountain Biking, Hiking & Golf/Sugarloaf condo A/C

Unwind in the comfort of air conditioning after a day of adventure. The condo features a fully equipped kitchen, modern living area, and access to an indoor pool and tennis courts. Enjoy convenient amenities, including Wi-Fi, parking, and in-house washer and dryer. Whether you’re seeking thrilling outdoor activities or a peaceful mountain escape, our condo is the ideal base for your next vacation. Book now and experience the best of mountain living!

FamilyValueKitchen

Popular amenities for Carrabassett Valley ski-in/ski-out rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/ski-out house rentals

5 out of 5 average rating, 6 reviews

Northwoods Ski in/Ski Out Home

FamilyLocationIndoor spaces

A stone pathway is framed by lush greenery, leading to a wooden porch elevated above the ground. The porch features natural wood elements and hanging plants, providing a welcoming appearance in a serene wooded environment.

Home in New Portland

5 out of 5 average rating, 3 reviews

4-Season Riverside Cottage near Sugarloaf

LocationIndoor spacesView

Superhost

A spacious living area features a large sectional sofa with various cushions, complemented by a dark coffee table. A flat-screen television is positioned above a fireplace. Large sliding doors allow natural light and views of the outdoor space, framed by trees outside.

4.74 out of 5 average rating, 46 reviews

Condo near wiffletree chairlift!

ValueFamilyAccess

The exterior of a modern condo is showcased against a mountainous backdrop, featuring a deck and surrounded by trees. Snow-capped slopes are visible in the distance, while the structure is set amidst a natural landscape, providing a serene atmosphere.

5 out of 5 average rating, 21 reviews

Mountainside - Ski In/Out Condo

FamilyLocationSkiing

Home in Dallas Plantation

An inviting living area features high, sloped ceilings and ample natural light filtering through large windows. Cozy seating is arranged around a circular coffee table, and the dining area is visible in the background. A warm, neutral color palette enhances the relaxed atmosphere.

4.98 out of 5 average rating, 45 reviews

Hot Tub | Game Room | Mountain Views | Sleeps 10

FamilyLocationSkiing

The spacious living area features hardwood floors and a stone fireplace. A large SMART TV is mounted on the wall, accompanied by comfortable seating. The kitchen is equipped with modern appliances and a breakfast bar with four stools, enhancing the functionality of the space.

5 out of 5 average rating, 22 reviews

Luxury 4bd/3.5ba Timbers Ski In/Out with Hot Tub!

FamilyLocationIndoor spaces

The exterior of the townhouse-style condo is framed by snow-covered trees, with a light yellow facade highlighting large windows. A snow-drift covers the pathway leading to the entrance, while wood logs are stacked neatly on the left side.

5 out of 5 average rating, 14 reviews

Town House at West Mountain

LocationHeatingWalkability

The three-story townhome building is set against a snowy mountain backdrop, with tree-lined areas in the foreground. The slopes of the mountain, visible in the distance, hint at the ski-in ski-out access available from the property.

Sugarloaf Ski In/Out - Fall Line

FamilyLocationIndoor spaces

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

Townhouse in Carrabassett Valley

A breathtaking aerial view captures a sprawling ski resort nestled among rolling mountains. Snow-covered trails meander down the slopes, leading to a cluster of buildings below. The landscape showcases a harmonious blend of white snow, evergreen trees, and distant peaks under a cloudy sky.

5 out of 5 average rating, 76 reviews

Year-round Sugarloaf Mountain Townhouse *w/ AC*

LocationFamilyCheckout

Cozy Retreat in Sugartree one

LocationSkiingCleanliness

A serene bedroom features a queen size bed with a bold black and white polka dot quilt. Decorative pillows with nature designs rest against a wooden headboard. Soft light is provided by a bedside lamp, and a framed landscape artwork hangs above the bed.

4.96 out of 5 average rating, 84 reviews

Sugarloaf Getaway

FamilyValueBathroom

Townhouse in Carrabassett Valley

A warm bedroom is presented with a spacious log bed, dressed in plaid bedding. Soft lighting from two bedside lamps creates a cozy atmosphere, while a window offers a view of the surrounding wooded area. A decorative 'SKI' sign adds a playful touch.

4.9 out of 5 average rating, 52 reviews

Sugarloaf Mt: on the mountain, indoor pool

FamilyLocationWifi

An aerial view captures the snowy landscape surrounding Sugarloaf USA, highlighting the ski slopes in the distance. The foreground features a cluster of townhouses nestled among trees, with a vast expanse of white snow covering the ground.

5 out of 5 average rating, 4 reviews

Suglarloaf Ski Condo

LocationFamilyParking

A cozy living area features a comfortable sofa and armchair, accented by a colorful rug. A wooden coffee table sits in the center, with a glass container atop it. Large doors open to a view of nature, and a flat-screen television is mounted on the wall.

5 out of 5 average rating, 6 reviews

Ski-In/Ski-Out West Mt. "Sweet" (apartment)

FamilyLocationDecor

Townhouse in Carrabassett Valley

A row of rustic wooden townhouses features multiple entries with glass panel doors. Snow-covered ground gives a wintery feel, and a parked vehicle is visible in front. The architecture exhibits natural wood finishes with a sloped gray roof.

West Mtn Townhouse at Sugarloaf

FamilyLocationComfort

Vacation home in Carrabassett Valley

An open living area is displayed, featuring a stone fireplace as a focal point. Comfortable seating options include two patterned armchairs and a neutral sofa. A dining table for 10 is visible, complemented by a well-equipped kitchen area. Natural light flows through several large windows.

4.92 out of 5 average rating, 50 reviews

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

FamilyLocationHospitality

Ski-in/ski-out condo rentals

The exterior of a two-story condo building is seen, with a snow-covered roof and trees stripped of leaves surrounding the property. A clear entranceway is visible, along with a parking area covered in snow. The overall environment reflects a winter setting.

4.95 out of 5 average rating, 40 reviews

ski in/ski out, 2 bedrooms, 2 baths, entire condo.

ValueFamilySkiing

A wooden Adirondack chair is positioned on a covered porch, facing a scenic view of snow-covered ground and distant mountains. Soft clouds drift across the sky, with a tree partially visible. The tranquil setting conveys an inviting atmosphere for relaxation.

4.98 out of 5 average rating, 61 reviews

Spacious Ski In-Ski Out 1BR with Fireplace&Hot Tub

FamilyLocationCondition

A sunlit living area features large windows that provide a view of the surrounding nature. A comfortable leather sofa faces a gas fireplace, with a coffee table and a lamp nearby. A small dining table is situated at the corner, complementing the cozy atmosphere.

5 out of 5 average rating, 25 reviews

2 BR+loft/2 Bath Ski-in Ski-out Snowflower condo

LocationFamilyAccess

4.92 out of 5 average rating, 24 reviews

Cozy Condo Park & Walk to the Village of Sugarloaf

ValueLocationView

A cozy living area features a modern entertainment unit with a flat-screen TV mounted on the wall. A wooden coffee table is positioned in front of a comfortable couch, complemented by a patterned rug. Natural light enters through a large window, with a view of the outdoors.

4.75 out of 5 average rating, 89 reviews

Sugartree II Ski in/ski out studio. Near Golf too

ValueLocationView

Superhost

Sugarloaf Village | Heart of Carrabassett Valley

LocationParkingNearby

A modern kitchen is featured with wooden cabinets and a central island. Stainless steel appliances, including a stovetop and hood, are visible. To the right, a cozy living area is accented by a stone fireplace and soft furnishings, inviting a sense of warmth.

4.96 out of 5 average rating, 68 reviews

Elegant Mountainside Sugarloaf Condo

FamilyValueKitchen