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

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, 5 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

A vibrant entryway showcases a door covered in a variety of stickers, creating a playful atmosphere. Hooks line the walls, adding functional charm, while natural light streams through the adjacent window. A welcome mat lies on the ground, enhancing the inviting entrance.

Apartment in Bridgton

5 out of 5 average rating, 17 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😎

Superhost

A comfortable living area features a stone fireplace and large windows allowing natural light. Two plush sofas are positioned around an area rug, while a dining table is set nearby. Elegant decor elements and wood accents enhance the serene environment.

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

Ski equipment is displayed on a wooden chair alongside a vintage slot machine. A red Coca-Cola cooler can be seen in the background, adding a nostalgic touch 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

A spacious living area is highlighted by a comfortable sectional sofa, inviting guests to relax. A stone fireplace sits in one corner, while large windows provide a view of the outdoors. A collection of games and books is stored on a nearby shelf.

Townhouse in Bridgton

4.67 out of 5 average rating, 21 reviews

Luxury Pleasant Mountain Condo near Moose Pond

Vacation in Maine at this beautiful condo/townhouse. Located on Pleasant Mountain (formerly Shawnee Peak) and across from Moose Pond, enjoy hiking, swimming, boating, and adorable Bridgton! Day trips: 40 minutes to North Conway, the White Mountains & Storyland, 1.5 hrs to Santa's Village & Kennebunk, and 1 hr to Portland! Wifi included. "The home is very comfortable and attractively decorated. Everything we looked for was provided, and the owners were wonderful to deal with."

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

Cozy Cabin on Pleasant Mountain - lakes & hiking!

Escape to this serene retreat at the base of Pleasant Mountain. This 4 bedroom, 2 bathroom skier'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, or exploring Bridgton, it's the perfect spot to call home on your getaway! With a direct access path to Pleasant Mountain, you'll never be without something to do!

A cozy living area is showcased, featuring a comfortable sofa and armchair, with a wooden coffee table in the center. Natural light filters in through window blinds. The walls are adorned with wooden paneling and decorative artwork, creating a warm atmosphere.

Cabin in Bridgton

4.75 out of 5 average rating, 4 reviews

Cozy slopeside 2 BR cottage perfect winter getaway

Relax with the whole family at this peaceful ski cottage, steps from the slopes of Pleasant Mountain Ski Resort. This cozy, comfortable cabin has a King size bed and two twin beds. Complete with full kitchen, refrigerator, oven and stove, coffee maker and sink. It also includes a washer/dryer, WiFi, 36in smart TV, grill and fire pit. Includes plenty of storage and parking. You can literally get your ski gear on and walk to the lifts!

A cozy living area is presented with a large maroon sectional sofa and a comfortable armchair. A wooden coffee table is centered on a light rug, while a stone fireplace adds warmth to the space. Walls are decorated with framed mountain-themed artwork.

Townhouse in Bridgton

4.94 out of 5 average rating, 16 reviews

Ski in Ski Out at Shawnee Peak

Shawnee Peak Ski In Ski Out Condo Enjoy the luxury of being slopeside at our beautiful, 3-story condo at the base of Shawnee Peak less than 30 minutes from the White Mountains area! Gorgeous views of the mountain from the living room and master bedroom. Sit by the cozy stone fireplace and have a front row seat to watch skiers on the slope right outside your window. Sleeps 10 comfortably. Perfect for two families to share.

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 snow-covered landscape captures the serene beauty of the region, with cozy townhomes nestled among tall trees. Ski trails are visible, surrounded by a blanket of white. The distant mountains create a tranquil backdrop against a clear blue sky.

Chalet in Bridgton

5 out of 5 average rating, 12 reviews

Pleasant Mountain - Ski In and Out

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

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.