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

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.

Wild house, for fun gatherings !Beach minutes

This romantic place to stay offers a history all its own. If you want to rent the barn for a big party, for example: your having a party and you want 40 people to stay for the night. Let me know how much people are planing to attend, and feel free to bring mattresses for yourselves. The barn includes electricity (in case you want to put heaters), chairs, tables, couches, and kitchen details.If your renting the barn for a place to sleep, make sure to get bio toilets and only use outdoor shower.

The Lil’ Chalet with Ski Mountain 15 min walk

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😎

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.

North Star Trailside • Hiking • Moose Pond

Looking for the perfect summer getaway? Stay in this brand-new log home on the East Side of Pleasant Mt, just steps from hiking trails and outdoor adventure. Enjoy nearby Moose Pond for swimming, fishing, and boat rentals, with the Saco River close by for day trips, canoeing, and tubing. Perfect for families or groups, relax in rustic luxury while being minutes from downtown Bridgton for dining, shopping, and summer events, and just 30 minutes to North Conway for more adventure and shopping.

Haggetts Haus

Escape to our updated Swiss-style chalet tucked in the woods of Bridgton, Maine—perfect for summer getaways. +Minutes to Moose Pond, Highland Lake, Pleasant Mountain, and other great hikes and beaches. +Relax on the deck surrounded by trees and the sound of birds. +Open-concept living with cathedral ceilings and modern kitchen. +2 private bedrooms + loft, 1.5 baths. +Quiet office for remote work. +Plenty of space for recreational gear. Ideal for lake days, hikes, and unwinding in nature.

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!

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!

Black Cabin Retreat-2BD/1B/Hot Tub/Ac/Wi-fi/W/D

Escape to our luxurious black cabin nestled in the woods of Harrison, ME, surrounded by mountains, fresh air, and peaceful nature. Perfect for summer getaways, this modern retreat features 2 cozy bedrooms, a private hot tub, AC, fast Wi-Fi, washer/dryer, and a full kitchen. Enjoy coffee on the deck, evenings by the fire, and nearby lakes including Long Lake (10 min), Crystal Lake (15 min), Highland Lake (20 min), and Sebago Lake (25 min). Perfect for relaxing year-round.

Silent Nights | Family Lake Retreat with Pool

Enjoy summer in Bridgton from this Knights Hill rental. Walk to the association beach on Moose Pond or take a short ride to the pool. Spend your days swimming, kayaking, boating, or exploring the Saco River for tubing and paddling. Hike nearby trails, or head 10 minutes to downtown Bridgton for dining and shops. Just 30 minutes to North Conway for even more adventure. Perfect for a relaxing Maine summer getaway.

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.

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.