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

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!

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.

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.

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, surrounded by mountains, lake views, and peaceful snowfall. Just minutes from ski resorts, this modern retreat is perfect for couples or families, with two cozy bedrooms, a spa-like hot tub, fast Wi-Fi, AC, washer/dryer, and fully equipped kitchen. Local snowmobile trails connect to the ITS system: Harrison/Bridgton 5–10min, Naples 20–25min, Lovell 25–30min. Relax by the fire, sip coffee on the deck, and enjoy nature year-round.

Stay 3 nts get 4th 1/2 off;stay 4 nts get 5th free

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

North Star Trailside Ski-In Ski-Out Lodge

Still looking for the perfect ski vacation? Stay in this brand-new, slope-side log home on the East Side of Pleasant Mountain, just 100 yards from the Sunnyside Triple Chairlift—skiing 7 days a week and night skiing 6 days a week. Perfect for families or groups, enjoy easy access to all Pleasant Mountain events, cozy rustic luxury, minutes from downtown Bridgton, and only 30 minutes to North Conway for shopping, dining, and more.

Silent Nights 5 Min to Mt Ice Fish & Wood Stove

Enjoy winter in Bridgton! Just minutes from Pleasant Mountain, this Knights Hill rental puts you right in the heart of all the winter fun. As the snow falls, spend your days skiing at Pleasant Mt., ice fishing or skating on Moose Pond, and exploring downtown Bridgton—only 10 minutes away for dining and shopping. Prefer a little outlet shopping or big-mountain fun? North Conway is just 30 minutes down the road.

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.