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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, 49 reviews

Farmhouse at Oxbow Beer Garden

MorganRating, 5 stars3 months ago
MAGIC. My husband spent a long weekend in the winter at this place and the property, house, and hosts were awesome. XC ski trails are right outside the front door. They were super well maintained and it was easy to rent equipment right on the property. The restaurant and beer garden is delicious. We ate there several nights and they have healthy options. The house had everything we needed including lots of linens and towels and extra blankets. The kitchen was well equipped. The hosts were super responsive via chat and very friendly. Looks like it would be really fun in summer but we had a great winter weekend.
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, 80 reviews

Easy Turns - Mountain Getaway

IvelinaRating, 5 stars8 months ago
We had a great time with the family at Laura’s place! Beautiful area, spacious house with everything needed. The fireplace was super nice in the cool nights and the game room was a nice entertainment. Private and surrounded by nature. Laura was very responsive and easy to communicate.
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 stars3 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 stars9 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 stars15 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.
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, 124 reviews

Fisher Ridge Yurt at Maine Forest Yurts

BrienneRating, 5 stars8 months ago
This was our second time staying with Maine forest yurts. Last year we stayed at the zen den and this year at fisher ridge. Just like last year the yurt did not disappoint! We love the friendly hosts and the beautiful area in which the yurts are located. Fisher Ridge yurt is very clean and spacious. We enjoyed kayaking and fishing in the ponds! I even caught a pickerel! My first freshwater fish (after getting my Maine fishing permit of course)! Jess and I want to make our visit to the yurts an annual experience and I cannot wait for next year! Thank you again!
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, 161 reviews

Moose Pond Mountain Escape

MelissaRating, 5 stars7 months ago
We had a lovely stay at James’ place! The hosts were very helpful and the area was beautiful. Would definitely recommend!

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