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

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

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

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

0 of 0 items showing

1 of 3 pages

Top guest favourite

Cabin in Bridgton

5 out of 5 average rating, 20 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!

Chalet in Bridgton

5 out of 5 average rating, 4 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.

Guest favourite

Flat in Bridgton

4.97 out of 5 average rating, 31 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😎

Guest favourite

Home in Bridgton

4.89 out of 5 average rating, 168 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

Home in Bridgton

4.8 out of 5 average rating, 10 reviews

The Ski Hive Trailside Pleasant Mnt

With over 1,400 groups of guests & 220 weddings across 1/2 dozen remarkable Maine properties, we provide Excellence & an Exceptional vacation experience. A husband/wife team that delivers remarkable large log home, farmhouse & lake homes 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/hiking right outside our front door.

Superhost

Home in Bridgton

4.83 out of 5 average rating, 18 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!

Top guest favourite

Home in Oxford

4.98 out of 5 average rating, 56 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 favourite

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

Superhost

Home in Bridgton

New place to stay

Lakes & Lifts Lodge

Ski-in/Ski-out on Pleasant Mountain! This spacious 2-bedroom, 2.5-bath East Slope condo puts you right on the trails for unbeatable mountain access. Perfect for families or friends, it offers an open layout, cozy fireplace, fully equipped kitchen, and plenty of room for everyone to relax after a day of adventure. Wake up to mountain views, step outside, and hit the slopes—it doesn’t get closer than this! Bring the whole family to this great place with lots of room for fun.

Top guest favourite

Home in Bridgton

5 out of 5 average rating, 25 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!

Guest favourite

Apartment 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 favourite

Home in Bridgton

4.91 out of 5 average rating, 66 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.