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Ski-in/Ski-out vacation rentals in Cumberland County

Find and book unique ski-in/ski-out homes on Airbnb

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Popular amenities for Cumberland County ski-in/ski-out rentals

Ski-in/ski-out house rentals

A two-story wooden home is showcased, featuring large triple-pane windows that allow ample natural light. A raised stone garden bed with assorted plants and flowers is featured in the foreground, along with a green lawn extending to the house.
Home in Otisfield
4.7 out of 5 average rating, 10 reviews

Brand new family home 3BR Sleeps 8

BethAnnRating, 5 stars82 months ago
The house is amazing! Our daughter loved watching the chickens in the morning and we enjoyed sitting on the porch at night. We also enjoyed reading about the eco-friendly construction of the house. Very inspiring!
Top guest favorite
A dining area features a large round wooden table surrounded by several wooden chairs. A long wooden bench runs along one side of the space. Sunlight enters through multiple windows, highlighting the warm wood flooring and natural light atmosphere.
Home in Bridgton
5 out of 5 average rating, 19 reviews

Cozy Knights Hill Home

KellyRating, 5 stars2 months ago
We had a great stay at the house. Chris and Nadine were very responsive and helpful with information. The house is so comfortable in terms of layout and has everything you need. We enjoyed sitting by the fire and relaxing at the end of the day. Would highly recommend this home if you are staying in the area.
Superhost
An aerial view captures a cluster of charming condo units surrounded by a wooded landscape. A serene lake is visible in the distance, accompanied by lush greenery. The remaining snow hints at seasonal changes, while the layout of the units emphasizes a harmonious connection with nature.
Home in Bridgton
4.8 out of 5 average rating, 15 reviews

Pleasant Mt. SLOPE SIDE Retreat!

ChrisRating, 5 stars3 months ago
We were late booking a MA school vacation week trip and luckily found this place at the last minute. Perfect ski in/ski out location and excellent condo. Comfortable, well stocked, with an ideal layout. William and David were great to deal with. Couldn’t have asked for a better ski vaca with the family. We hope to stay again next year!
Guest favorite
Home in Bridgton
4.88 out of 5 average rating, 16 reviews

Elegant 6BR Home w/ extra 1BR loft Airbnb option

ScottRating, 5 stars8 months ago
OMG The Manor at Boho Ridge was the perfect AirB&B for me and my friends for another friends son’s wedding near by. My friends were blown away at how beautiful this house is. The amenities, cleanliness & comfort that this house offers is second to none. I’ve been to a few AirB&B’s lately and this house was stocked beyond compare both in the kitchen & all the bathrooms. I probably don’t have to return to Maine anytime soon but if I did this would be the place I would choose. If you’re choosing a house in the area this is the one. Highly recommended for families or groups. We were 8 people and had room for at least 2 more if not 4 more.
Guest favorite
The exterior of a red lodge is surrounded by vibrant autumn foliage. Tall trees provide a natural frame, while a stone chimney adds rustic charm. A gravel driveway leads to the building, showcasing a welcoming entrance with a distinctive green door and decorative elements.
Home in Bridgton
4.92 out of 5 average rating, 61 reviews

New England Lodge in Western Lakes Region of Maine

SteveRating, 5 stars1 month ago
Warm and very well-equipped cottage for groups.
Guest favorite
Home in Oxford
4.98 out of 5 average rating, 50 reviews

Farmhouse at Oxbow Beer Garden

KhrisRating, 5 stars1 week ago
We had a wonderful and relaxing time! beautiful charming house. Location was super convenient! we hung out at the Beer Garden A lot! love it! Host Renee was super friendly and responsive. We highly recommend. P.s The house is now black.
Guest favorite
A welcoming exterior view of the home showcases a spacious covered porch, surrounded by vibrant greenery and well-maintained flower beds. The façade blends natural tones with white accents, complemented by a second-story balcony framed by trees, enhancing the connection to the serene surroundings.
Home in Bridgton
4.98 out of 5 average rating, 81 reviews

Easy Turns - Mountain Getaway

JeanRating, 5 stars8 months ago
Our stay was wonderful! The house was spotlessly clean. Well equipped kitchen, everything you could need. Great playroom with lots to do downstairs. TV games bar etc. We would stay here again without question. Thank you Laura, Jean and Ira
An open barn space features warm wooden beams and a polished wooden floor. Soft lighting strung across the ceiling creates a welcoming ambiance. A long dining table is set with dark chairs, ready for gatherings or celebrations.
Home in Standish
4.25 out of 5 average rating, 12 reviews

Party’s , for large groups !Beach minutes

BethanyRating, 5 stars10 months ago
Our bachelorette party of 14 guests fit comfortably in this space. This home is lovely and comfortable (it took me a bit to figure out the AC on day one, but after the first night the place got a lot cooler). Avigeya was extremely helpful and kind with communicating and making the space welcoming for us. We are all extremely satisfied with our experience staying at this house in Standish. Thank you! 🤗

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

Guest favorite
The exterior of a red lodge is surrounded by vibrant autumn foliage. Tall trees provide a natural frame, while a stone chimney adds rustic charm. A gravel driveway leads to the building, showcasing a welcoming entrance with a distinctive green door and decorative elements.
Home in Bridgton
4.92 out of 5 average rating, 61 reviews

New England Lodge in Western Lakes Region of Maine

SteveRating, 5 stars1 month ago
Warm and very well-equipped cottage for groups.
Superhost
The image captures a row of rustic condos, characterized by wooden exteriors and peaked roofs. The setting features a rocky foreground and distant hills under a clear blue sky. Surrounding trees complement the natural landscape, enhancing the outdoor environment.
Condo in Bridgton
4.81 out of 5 average rating, 48 reviews

Pleasant Mountain Shawnee Peak Slope side condo

ErinRating, 5 stars4 months ago
The ski in ski out at Pleasant Mountain is hard to beat for families. The hosts were super responsive and our party of 8 had a great time.
Superhost
A spacious yurt is surrounded by tall trees in a wooded setting. A wooden picnic table is positioned nearby, along with a charcoal grill and a small storage shed. The yurt features a green exterior and a circular design, inviting a nature-filled experience.
Yurt in Durham
4.93 out of 5 average rating, 85 reviews

Hemlock Ridge Yurt at Maine Forest Yurts

JanetRating, 5 stars10 months ago
We were exhausted but finally got to the yurt & it was incredible. Felt like 100 acres all to ourselves / our dog! We slept most of the time but the little exploring we did / our dog was just beautiful, quiet, relaxing!
A spacious living area features a large gray sectional sofa, inviting relaxation. A round area rug with multi-colored patterns complements the room's warm tones. In the background, a dining table and kitchen area are visible, creating a cohesive and comfortable gathering space.
Townhouse in Bridgton
4.67 out of 5 average rating, 21 reviews

Luxury Pleasant Mountain Condo near Moose Pond

JennaRating, 5 stars16 months ago
We had a wonderful ski weekend with two families at the condo. It's a perfect location and very comfortable. We enjoyed all the games and toys provided for those who don't ski. The listing was as pictured and we felt at home right away.
Top guest favorite
A spacious outdoor area is surrounded by trees, featuring a yurt on one side and a wooden structure on the other. Several outdoor chairs are arranged around a fire pit, creating a cozy gathering spot amidst nature.
Yurt in Durham
4.93 out of 5 average rating, 126 reviews

Fisher Ridge Yurt at Maine Forest Yurts

JenniferRating, 5 stars1 week ago
What a beautiful setting this family has created! The yurts were exactly what we wanted and Page and Bob were enjoyable, kind, interesting hosts. We'll definitely return!
A two-story wooden home is showcased, featuring large triple-pane windows that allow ample natural light. A raised stone garden bed with assorted plants and flowers is featured in the foreground, along with a green lawn extending to the house.
Home in Otisfield
4.7 out of 5 average rating, 10 reviews

Brand new family home 3BR Sleeps 8

BethAnnRating, 5 stars82 months ago
The house is amazing! Our daughter loved watching the chickens in the morning and we enjoyed sitting on the porch at night. We also enjoyed reading about the eco-friendly construction of the house. Very inspiring!
Guest favorite
A chalet-style home is nestled among tall trees, featuring a wooden deck with a set of stairs leading down to the ground. Large windows provide glimpses into the living spaces, welcoming natural light into the interior.
Home in Bridgton
4.88 out of 5 average rating, 162 reviews

Moose Pond Mountain Escape

PhilRating, 5 stars2 days ago
We had a great time at Jim and Gwens place in Knight's Hill. The amenities were great and the location provided us with everything we were looking for near Moose Pond. Would highly recommend.

Destinations to explore