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

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

Top-rated ski-in/ski-out rentals in Cumberland County

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

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Top guest favorite

A cozy living area features a large brown leather sofa facing a television mounted above a brick fireplace. Natural light pours in from large windows, and a wooden dining table with white chairs is visible in the open-concept space. A patterned area rug adds warmth to the floor.

Cabin in Bridgton

5 out of 5 average rating, 14 reviews

Haggetts Haus

Escape to our recently updated 1973 Swiss-style ski chalet in the serene woods of Bridgton, Maine. +Short walk to Pleasant Mountain Ski Resort slopes and lodge. +Gear room for skis, boots, and beach gear, plus a cozy TV/game area. +Open-concept kitchen with granite countertops, dining/living area with cathedral ceiling, and views of wooded mountainside. +Two full bedrooms, loft with 3 twin beds, 1.5 baths. +Thermostat-controlled propane fireplace, all-new furnishings. Perfect for all seasons!

A cozy bedroom features natural wood walls and ceiling beams. A spacious bed is adorned with a colorful quilt. Windows allow natural light to fill the room, while a small nightstand and lamp are visible beside the bed, adding functional warmth.

Chalet in Bridgton

5 out of 5 average rating, 3 reviews

Ski & Lake Retreat w/ Epic Views

Perched on the slopes of Pleasant Mountain in the exclusive Trailside Woods community, this custom log chalet offers true ski-in/ski-out access and panoramic views of Moose Pond. Whether you're hitting the slopes in winter or soaking in the natural beauty year-round, this chalet delivers the perfect blend of adventure and relaxation. Located just minutes from downtown Bridgton, 30 minutes from North Conway, and less than an hour from Portland, it's the ideal base for your next mountain getaway.

A spacious living area is highlighted by a high, wooden ceiling and large windows, providing abundant natural light. A comfortable sectional couch, wooden coffee table, and stone fireplace create a welcoming gathering space. The adjacent kitchen area is visible, showcasing an open layout.

Home in Bridgton

4.78 out of 5 average rating, 9 reviews

The Ski Hive Trailside Pleasant Mnt

With over 1,000 groups of guests & 200 weddings under our belt, across 1/2 dozen Maine properties, we provide excellence & an exceptional vacation experience. A husband/wife team that delivers remarkable, large Log Home & Farmhouses that provides a quintesential Maine experience. With 3 floors of living space & 5 bedrooms, this home can fit the entire family. Located Trailside at Pleasant Mnt Ski Area, this property boasts breathtaking views & skiing/riding/hiking right outside our front door.

Top guest favorite

A serene lakeside view is presented, featuring a sandy beach area leading to calm waters. Blue skies with scattered clouds reflect softly on the lake's surface, while trees border the shore, enhancing the peaceful ambiance of the natural setting.

Apartment in Bridgton

4.97 out of 5 average rating, 29 reviews

The Lil’ Chalet with Association Beach Access

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 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

4.89 out of 5 average rating, 166 reviews

Moose Pond Mountain Escape

A two minute walk to Moose Pond and one mile from Pleasant Mtn skiing in picturesque Bridgton, Maine. This cozy retreat is perfect for those who want a relaxing getaway in a fun-filled area in the heart of the lakes region. Guests enjoy a short walk to Association's beach/dock access and kayaks, and a short drive to tennis courts and pool. Hike, bike and explore Western Maine's mountains, lakes and villages. Bridgton shops are 5 miles away while N. Conway's outlets are 20 miles to the east.

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

4.82 out of 5 average rating, 17 reviews

Pleasant Mt. SLOPE SIDE Retreat!

Welcome to our stunning and spacious condo unit nestled directly on the slope of Pleasant Mountain, offering breathtaking views and a tranquil experience. Situated directly across from Moose Pond, this unique vacation rental promises a memorable retreat in a location that seamlessly blends natural beauty with elegant design. The surrounding area offers an array of activities and attractions for outdoor enthusiasts and nature lovers. Book now and experience this unforgettable vacation!

A bright living area features exposed wooden beams and light-colored walls. Two comfortable sofas are arranged around a coffee table, with decorative cushions adding subtle detail. Natural light filters through multiple windows, creating an inviting space, while artworks hang on the walls.

4.98 out of 5 average rating, 54 reviews

Farmhouse at Oxbow Beer Garden

Come and enjoy a relaxing staying at this unique farmhouse in the foothills of Western Maine. This 200 year old home is adjacent to Oxbow Beer Garden (bar & restaurant) and centrally located to many beautiful lakes and mountains. In the winter months this home is a great launching place for skiers and snowmobilers alike, with ski-on ski-off access to Oxbow’s Nordic trails and the local snowmobile trail network. The warmer months offer countless local options for fishing, hiking and more!

A warm kitchen area features a central island surrounded by black chairs. A wooden dining table with matching benches sits nearby. Large windows let in natural light and showcase the greenery outside, while wood paneling adds a rustic charm to the space.

Chalet in Bridgton

5 out of 5 average rating, 34 reviews

Summer is here- hiking and biking are all here!

Come stay at this newer home. High end appliances, Gas fireplace and radiant heat make this home warm - 4 BR and 3 full baths- sleep up to 10 people. Pleasant Mt is only yards away from your door! 20 min to No Conway for shopping. Moose Pond is a min drive away! Adults can gather in the kitchen around the island for grown-up time while the kids head downstairs to play ping-pong, shoot pool or play on a real arcade game with more than 50 games or play a round of electronic basketball

The spacious exterior of the home is framed by lush greenery, with a wide porch showcasing seating areas. Sunlight filters through the trees, illuminating the well-manicured lawn. The house features a light yellow exterior and multiple windows, inviting a sense of openness.

Home in Bridgton

4.91 out of 5 average rating, 22 reviews

Peaceful estate w/ 1BR loft option, sleeps 13

Nestled on 20 acres of serene fields and woods, this luxurious home offers a peaceful retreat while being conveniently located close to town and nearby ski resorts. Whether you're seeking a peaceful getaway or an adventure-filled vacation, this has everything you need. Additional 1 bedroom loft airbnb above the garage with separate entrance. Special events and weddings require additional permission. (Extra fees)

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, 22 reviews

Cozy Knights Hill Home

Enjoy summer in Bridgton! Relax at the Knights Hill association beach and outdoor pool. Take the kayak or canoe and explore Moose Pond. Bring your boat and use public boat launch just 1.5 miles away. This charming Knights Hill rental is minutes from Bridgton's dining, shopping, and outdoor fun, and only 30 minutes from North Conway for outlet shopping and more summer adventures!

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

Great 3 level slope side condo at Shawnee Peak. Accessible for both day and night skiing. Master bedroom and second bedroom on top floor, main floor with full kitchen and living area with fireplace. 1st floor has additional beds and seating area, great for the kids. Short walk to the main lodge and Blizzards pub for dinner and apres ski. Wifi and cable included.

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, 64 reviews

New England Lodge in Western Lakes Region of Maine

A New England Ski Lodge located in the beautiful Western Lakes Region of Maine. Just one hour from Greater Portland and a half hour to Mount Washington Valley. The area offers great opportunities for the outdoor enthusiast for all seasons. Enjoy hiking the local mountains, fishing or boating on nearby Moose Pond or paddling or tubing down the Saco River.

Vacation rentals for every style

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Apartments

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Kick off your hiking boots at these rustic lodgings

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

Free parking on premises

Air conditioning

Ski-in/ski-out house rentals

A wooden dock extends into calm waters, leading toward a lush tree-lined shore in the distance. A dog stands on the dock, looking ahead, while the rippling surface of the water reflects the surrounding landscape.

Home in Bridgton

Mountainside

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, 22 reviews

Cozy Knights Hill Home

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

4.82 out of 5 average rating, 17 reviews

Pleasant Mt. SLOPE SIDE Retreat!

The spacious exterior of the home is framed by lush greenery, with a wide porch showcasing seating areas. Sunlight filters through the trees, illuminating the well-manicured lawn. The house features a light yellow exterior and multiple windows, inviting a sense of openness.

Home in Bridgton

4.91 out of 5 average rating, 22 reviews

Peaceful estate w/ 1BR loft option, sleeps 13

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, 64 reviews

New England Lodge in Western Lakes Region of Maine

A bright living area features exposed wooden beams and light-colored walls. Two comfortable sofas are arranged around a coffee table, with decorative cushions adding subtle detail. Natural light filters through multiple windows, creating an inviting space, while artworks hang on the walls.

4.98 out of 5 average rating, 54 reviews

Farmhouse at Oxbow Beer Garden

A rustic stone fireplace serves as the focal point in the living room, with a gentle flame flickering inside. A wooden coffee table showcases magazines, while surrounding seating includes a black armchair and a brown leather sofa. Soft white curtains frame the windows on either side.

Home in Bridgton

4.98 out of 5 average rating, 83 reviews

Easy Turns - Mountain Getaway

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

4.33 out of 5 average rating, 15 reviews

Family , Friends cozy gatherings Bech minutes

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

Top guest favorite

A bright kitchen space features green cabinets and a stainless-steel stove. A round dining table with red chairs sits by a large window, offering a view of the outdoors. A rustic area rug adds warmth to the wooden floor.

Farm stay in Brunswick

4.98 out of 5 average rating, 97 reviews

Brunswick Farm Stay

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, 22 reviews

Cozy Knights Hill Home

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

4.82 out of 5 average rating, 17 reviews

Pleasant Mt. SLOPE SIDE Retreat!

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

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, 64 reviews

New England Lodge in Western Lakes Region of Maine

A bright living area features exposed wooden beams and light-colored walls. Two comfortable sofas are arranged around a coffee table, with decorative cushions adding subtle detail. Natural light filters through multiple windows, creating an inviting space, while artworks hang on the walls.

4.98 out of 5 average rating, 54 reviews

Farmhouse at Oxbow Beer Garden

Top guest favorite

A serene lakeside view is presented, featuring a sandy beach area leading to calm waters. Blue skies with scattered clouds reflect softly on the lake's surface, while trees border the shore, enhancing the peaceful ambiance of the natural setting.

Apartment in Bridgton

4.97 out of 5 average rating, 29 reviews

The Lil’ Chalet with Association Beach Access

A rustic stone fireplace serves as the focal point in the living room, with a gentle flame flickering inside. A wooden coffee table showcases magazines, while surrounding seating includes a black armchair and a brown leather sofa. Soft white curtains frame the windows on either side.

Home in Bridgton

4.98 out of 5 average rating, 83 reviews

Easy Turns - Mountain Getaway

Destinations to explore