Ski-in/Ski-out vacation 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.

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, 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.

Get some last min skiing in! Pleasant Mtn is open!

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

Cozy Knights Hill Home

Enjoy summer in Bridgton! Just minutes from Pleasant Mountain, this Knights Hill rental is perfectly located for warm-weather fun. Walk to the association beach on Moose Pond or take a short ride to the association pool. Spend your days swimming, kayaking, or boating, or take a day trip to the Saco River for tubing and paddling. Explore downtown Bridgton—only 10 minutes away—for dining, shops, and local events. North Conway is just 30 minutes away for even more adventure.

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

Escape to our luxury Black Cabin, a peaceful woodland retreat with mountain and lake views. 🌲 Just minutes from ski resorts, it’s perfect for couples or families. Enjoy 2 cozy bedrooms, a private hot tub, fast Wi-Fi, AC, washer/dryer, and a fully equipped kitchen. Relax by the fire or sip coffee on the deck after a day of skiing or snowmobiling. Trails connect to the ITS system nearby. Your perfect Maine getaway awaits year-round. 🏔️✨

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.