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

Rental unit in Bridgton

5 out of 5 average rating, 5 reviews

Lil’ Ski Chalet-Ski In/Ski Out!

This unique "Arched Cabin" is located on the side of Pleasant Ski Mtn off of Rabbit Run Trail. 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 shared in the House Book. Be our guest...And let the good times begin!

Guest favorite

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

Home in Bridgton

4.77 out of 5 average rating, 13 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

Chalet in Bridgton

5 out of 5 average rating, 33 reviews

Come and stay for Turkey Day! Ski Mt Pleasant soon

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

Home in Oxford

4.98 out of 5 average rating, 44 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 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, biking, hiking and more!

Guest favorite

Home in Bridgton

4.95 out of 5 average rating, 20 reviews

Chalet ON Ski Mtn w/Beach! New kitchen!

Bring your family to this private & peaceful newly renovated chalet, slope-side neighborhood of Pleasant Mountain; special association access to the large sandy beach of Moose Pond right off of Rte 302. 1973 ski chalet; stylishly refreshed for your vacation needs and comforts. Loon Echo Trust trails out the front door, Canoe/kayak at the beach for your exclusive use, fire pit, outdoor seating, & cozy kids’ loft! Thoughtfully managed and “super hosted” by Heather!

Guest favorite

Cabin in Bridgton

5 out of 5 average rating, 21 reviews

Pleasant Mountain Cabin - Ski-In/Out & Lake Views!

Nestled atop Trailside Woods community on the east side slope of Pleasant Mt, this custom log cabin offer skiing ski in/out access with breathtaking views of moose pond. Come see how beautiful Pleasant Mt is this winter. Only a short drive to Bridgton’s downtown for shops and restaurants, 30 minutes to North Conway, under an hour from Portland. This location is perfect for both relaxation and adventure year-round. Don’t miss this opportunity!

Guest favorite

Rental unit in Bridgton

4.97 out of 5 average rating, 88 reviews

“The Loft” at Boho Ridge

Escape to our perfect luxury loft apartment for your next romantic getaway or family vacation. With an open floor plan, full kitchen, electric fireplace, smart TV, heat/AC, washer/dryer, and private office space, you'll have everything you need to relax and unwind. Book now! This unit is situated above the garage. The main home (attached) is also an airbnb called “The Manor”. Rent just the loft or rent both for your large gathering!

Chalet in Bridgton

5 out of 5 average rating, 7 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

Condo in Bridgton

4.79 out of 5 average rating, 42 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

Home in Bridgton

4.92 out of 5 average rating, 59 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.

Townhouse in Bridgton

4.75 out of 5 average rating, 24 reviews

Off-Season Mtn Retreat • Hiking & Lakes Nearby •

Stay slopeside in our 3-level condo on Pleasant Mountain. Fully furnished with dedicated parking, open kitchen/dining/living with hardwood floors, lower level family room, deck to relax and grill, and master bedroom balcony. Hike the nearby mountain trails or enjoy all the water activities the local lakes have to offer.