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

4.85 out of 5 average rating, 181 reviews

A two-story home is surrounded by trees, with a welcoming front porch and outdoor seating area. The yard features a well-maintained lawn and stone path, ideal for relaxation and enjoying the natural scenery.

Home in Rumford

Sunnyside close to Sunday River/Black Mt A/C

Sunnyside is the perfect getaway for the family, a group of friends, or couples looking for peace and quiet. In the winter, come enjoy easy access to Sunday River, (20 minutes drive) Black Mountain, ( 7 minutes drive) and Mount Abram -30 minute. In the summer swimming (Ellis Pond, Roxbury Pond) for hikers, Whitecap Mountain Preserve. The trail is great for camping and hiking! Fall foliage is a stunning spectacle. Our home is perfect for your next vacation and we're looking forward to sharing it.

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.

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!

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, 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!

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.

4.92 out of 5 average rating, 12 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.

An aerial view captures the Sugarloaf mountain and surrounding area, showcasing snow-covered slopes and trails. The Snubber Chairlift is visible along with several snow-dusted buildings nestled among evergreen trees, highlighting the winter landscape.

4.97 out of 5 average rating, 31 reviews

Beautiful Ski InSki out 5 Bedroom Condo Townhouse!

This newly listed condo is the perfect spot for your vacation. A tastefully decorated and vibrant condo centrally located on Sugarloaf mountain. A ski in, ski out property with a chairlift right out back. This spacious and well lit condo features a sunny living room, 4 bedrooms, 3.5 bathrooms, and much more. The kitchen is stocked with everything you need to cook your favorite meals. The living room is comfortable and cozy with hardwood floors and a fireplace to enjoy after a day of skiing!.

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.

4.89 out of 5 average rating, 9 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.

Superhost

A view from a window showcases snow-covered grounds and a series of light blue buildings nestled against a backdrop of a snow-capped mountain. The bright sunlight creates a serene winter landscape.

Flat in Carrabassett Valley

4.86 out of 5 average rating, 7 reviews

Updated Family Ski-In/Out Condo w/ Pool Access

This bright, updated 2-floor, 3-bedroom, 3-bath family condo is a ski-in/ski-out gem located in the popular slope-side Snowbrook neighborhood at Sugarloaf. You will be steps from the Snubber chairlift, as well as a trail system for hiking or cross-country skiing - plus, you will have access to the Association pool and hot tub facilities. The free shuttle service running from the top of the parking lot to the base of the mountain means you can park your car and focus on fun on the slopes!

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.

4.96 out of 5 average rating, 103 reviews

Ski In/Ski Out Sugarloaf Sugartree 2 Deluxe Studio

This cozy and comfy ski in/ski out condo is in a desirable location and just a short chairlift ride to the base of Sugarloaf Mountain. Ski or mountain bike directly from the condo! Family friendly. A queen bed settled in an alcove, queen murphy bed and pull out full size sofa bed provide plenty of sleeping space. Convenient indoor access to the pool, hot tubs, and sauna at the Sugarloaf Sports and Fitness Center (additional fees apply). Full kitchen, and one of the few with AC for summer!

4.91 out of 5 average rating, 106 reviews

A scenic lakeside view captures the sunset reflecting on the water, outlining the dock and several boats nearby. The grassy area leads to the water's edge, with trees providing natural framing to the picturesque setting of the Lake House.

Home in Oakland

Lake-House on water, East Lake, Near Waterville

Welcome to the Lake House! 5 bedrooms. Access to a mooring. Full bathroom and kitchen with accessories. Bedrooms have locked doors & Wi-Fi. The house has a Deck and Docks, 8 foot by 10 foot floating Island, BBQ Grill. Lakeside Bon Fire Pit. Full bath, 30 feet from Lake! 2 entrances, 3 Kayaks, Fishing/Swimming. Nice neighbors including Camp Manitou, Matoaka and Somerset. Near Public Boat Landing & country store. I reside nearby, and will help with any issues.

4.98 out of 5 average rating, 134 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

Mountainside at Saddleback - Sunsets! Views!

Welcome to the Last Chair Lodge - our family-friendly mountainside retreat at Saddleback Ski Area in Rangeley, ME. 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. Yes, we have A/C and fast fiber WiFi! HDTV w/streaming services included.

A welcoming three-story, wooden townhouse is showcased, featuring a combination of stone and wood siding. The entrance includes two front doors framed by large windows. A wooden staircase leads to the entryway, surrounded by a gravel path and a rock border.

4.97 out of 5 average rating, 62 reviews

6011 Allagash Drive at Sugarloaf

1,200 square foot townhouse on West Mountain. On mountain convenience, with off the beaten path quietness. It is about a 3-4 minute walk to the West Mountain chair, for 'almost' ski-in ski out convenience. The Explorer Shuttle comes right to the development 3 times an hour on weekends, 2 during the week. Top of the line finishes, fireplace, laundry, gourmet kitchen with exceptional cookware. 1 King Bed in master and a Queen bed in each other room.

Holiday 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.

4.93 out of 5 average rating, 45 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.

Popular amenities for Carrabassett Valley ski-in/out rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/out house rentals

5 out of 5 average rating, 3 reviews

Fun and spacious central two bedroom with views

The exterior of the upper-level condominium is showcased, featuring a blend of screened-in porches and large windows. The surrounding grassy area provides a natural setting, with trees visible in the background and a clear blue sky above.

4.81 out of 5 average rating, 36 reviews

*New to Market* 410 Snowflower

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

A full-sized house is shown, featuring a light green exterior with large glass doors providing access to a deck. Window designs include a semicircular arch at the top. Surrounding trees lend a natural backdrop to the peaceful setting.

Home in Kingfield

The Skyline House

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.

4.72 out of 5 average rating, 36 reviews

Condo near wiffletree chairlift!

Modern Ski and Golf - West Mnt

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, 8 reviews

Town House at West Mountain

The living area features a cozy arrangement of green sofas facing a media console with a television. A patterned area rug adds warmth, while a stone fireplace provides a focal point. Natural light filters through large windows adorned with decorative curtains.

4.79 out of 5 average rating, 19 reviews

Sugarloaf Mountainside Cabin

Family-friendly, ski-in/out home rentals

Superhost

A welcoming sign stands at the entrance of Fall Line Condominiums, framed by snow-covered ground and towering evergreen trees. The sign highlights Frank's Bar and Grille, indicating a dining option nearby.

Chalet in Newry

Fall Line Ski in/out. Sleeps 6

An open living space features a cozy seating area with light gray sofas and a central coffee table. A staircase leads to the upper level, while a fully equipped kitchen is visible in the background. Natural light is welcomed through the windows.

4.95 out of 5 average rating, 20 reviews

Brookside II B-303 - Sunday River Condo

4.75 out of 5 average rating, 55 reviews

Brookside 1B403 · Slopeside Sunday River Condo Bro

4.97 out of 5 average rating, 74 reviews

The exterior of the FunHouse is showcased at night, featuring a modern chalet design with large windows and a combination of wood and stone materials. A snow-covered deck surrounds the entrance, with stair steps leading up to the front door. Warm light glows from within.

Home in Newry

FUNHOUSE

A spacious living area features a large sectional sofa adorned with patterned throw pillows. A sturdy coffee table sits in the center, complemented by two side tables. Natural light streams through the window, highlighting decorative wall art and a cozy carpeted floor.

5 out of 5 average rating, 33 reviews

Ski in/out Fall Line condo with tons of amenities!

An aerial view displays the expansive snowy landscape of Sunday River, highlighting the ski slopes that wind through the mountains. The condo's location is marked, positioned conveniently near the base area for easy access to outdoor activities.

4.92 out of 5 average rating, 104 reviews

Slope Side | Ground floor | Hot Tub, Pool, Sauna

A multi-level townhouse is visible against a clear blue sky, with ski lifts transporting guests overhead. The building features a combination of light and dark siding, and balconies are apparent on the upper levels, surrounded by snow-covered ground and trees.

4.87 out of 5 average rating, 250 reviews

Sunday River Locke Mountain Ski In/ Ski Out Pool

Aerial view of Sunday River ski resort showcases snow-covered slopes with multiple ski trails winding down the mountainside. The lodge buildings are visible at the base, surrounded by a winter landscape of evergreen trees and mountainous terrain under a partly cloudy sky.

4.93 out of 5 average rating, 15 reviews

Sunday River Studio (Ski In/Out)

Ski-in/out apartment rentals

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, 44 reviews

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

A view of Sugarloaf Mountain dominates the image, featuring a snow-covered landscape and distinct skiing trails. A mix of evergreen trees is positioned in the foreground, framing the mountain and creating a natural border. The sky is clear, highlighting the mountain's rugged terrain.

5 out of 5 average rating, 9 reviews

Winter's Way Sugarloaf Getaway

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, 16 reviews

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

Superhost

A panoramic view showcases a snow-covered mountain adorned with ski trails under clear blue skies. The surrounding area features a collection of rooftops nestled among trees, with key locations like Beaver Brook and the Snubber Chairlift marked for easy navigation.

4.75 out of 5 average rating, 8 reviews

Ski In Ski Out Cozy Condo, Indoor Pool Access!

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.

4.74 out of 5 average rating, 80 reviews

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

The living room features a stone fireplace surrounded by cozy seating arrangements, including a brown couch and two chairs. A television is mounted on the wall beside bookshelves filled with books. A wooden coffee table sits on a patterned rug, with a window dressed in light curtains allowing natural light.

5 out of 5 average rating, 8 reviews

Trailside Ski Retreat

The exterior of a multi-story condominium is displayed, covered in a layer of snow. The backdrop features Sugarloaf Mountain, showcasing its ski trails and winter landscape. Clear blue skies provide a vibrant contrast to the snow-covered scenery.

4.91 out of 5 average rating, 85 reviews

Sugarloaf On Mountain Condo! Ski In/Out