Ski-in/out vacation 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.

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Guest favourite

Apartment in Bridgton

5 out of 5 average rating, 9 reviews

Lil’ Ski Chalet-Ski In&Out-Private Assoc. Beach!

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/Beach access in House Book.

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!

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 favourite

Home in Oxford

4.98 out of 5 average rating, 46 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!

Superhost

Cabin in Bridgton

5 out of 5 average rating, 3 reviews

Cozy Cabin on Pleasant Mountain -5 min walk to ski

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!

Guest favourite

Cabin in Bridgton

5 out of 5 average rating, 24 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!

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!

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.

Chalet in Bridgton

5 out of 5 average rating, 8 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

4.8 out of 5 average rating, 44 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

4.92 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.