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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Guest favorite

An open-concept living space features wood-paneled walls and vaulted ceilings with exposed beams. A large dining table is surrounded by metal chairs, while a cozy seating area with a light-colored sofa is illuminated by natural light from expansive windows.

Cabin in Bridgton

5 out of 5 average rating, 8 reviews

Gorgeous Cabin minutes to Moose Pond & Lake Kezar!

Escape to this serene retreat at the base of Pleasant Mountain. This 4 bedroom, 2 bathroom outdoor enthusiast's dream cabin is the ideal home base for families and groups. The open-concept layout offers a cozy but spacious living area, fully equipped kitchen and large bedrooms. Whether you spend your days skiing, hiking, swimming in the lakes, or exploring Bridgton, it's the perfect spot to call home on your getaway! With a direct access path to Pleasant Mountain, you'll run out of things to do!

Superhost

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

5 out of 5 average rating, 6 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.

Guest favorite

The arched cabin is illuminated by soft outdoor lighting, showcasing its wooden exterior covered in a layer of fresh snow. Tall windows at the front hint at a warm interior, surrounded by a winter landscape of trees and snow-covered ground.

Apartment in Bridgton

5 out of 5 average rating, 19 reviews

The Lil’ Chalet-Assoc. Beach-NO Cleaning Fee!

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😎

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

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.

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!

Welcome to our stunning 3-bedroom condo unit nestled on the picturesque 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!

Guest favorite

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.

Home in Oxford

4.98 out of 5 average rating, 48 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!

Guest favorite

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

April vacation open - great skiing still available

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

Guest favorite

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

4.88 out of 5 average rating, 16 reviews

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

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)

Guest favorite

A serene view of Pleasant Mountain is framed by lush green foliage. The calm waters reflect the mountain and cloudy sky, creating a peaceful natural scene. Occasional rocks are visible in the foreground, enhancing the tranquil atmosphere.

Chalet in Bridgton

5 out of 5 average rating, 12 reviews

Luxurious Mountain Summer Retreat at Moose Pond

Looking for an escape? Short term or maybe Long Term? You found the perfect location for your next Maine adventure. Amazing location directly on PLEASANT MOUNTAIN (formerly SHAWNEE PEAK), with Ski IN/OUT Access! 3* Bedrooms, 2 full baths 1 half, 2 decks, 1 porch, 3 level townhome. Perfect retreat to unwind in nature - 2.5 hrs from Boston and less than 1 hour from Portland, ME - 20 min to North Conway

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

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!

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

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.

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

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.