Chalet 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.

Good Times Chalet Limit 19

GOOD TIMES CHALET 4 bedrooms with loft and bunk room. Sleeps 19 OCCUPANCY LIMIT 19 MOOSE POND - KNIGHT'S HILL COMMUNITY. **This Place Has It All** Located in desirable Knights Hill Association on Moose Lodge in Bridgton. Four bedrooms (plus additional sleeping in loft and finished lower level) allows for sleeping for up to 19. The basement area that sleeps 8 is suitable for teens and young adults. Three bathrooms, well stocked kitchen, great room with large flat screen TV, cable and internet.

Maine A-Frame with Hot Tub, Game Room, Lake Access

Escape the city and relax at Camp Merryweather. Our A-Frame is perfect for a romantic getaway or a family retreat with the kids and dogs welcome! If you’re a work from home professional looking to escape your normal routine, we’ve got you covered! With a fully equipped work space and reliable high speed internet you can break free from the pressures of the city while still staying connected. Enjoy our hot tub and game room Come experience our slice of heaven for yourself, you won’t regret it!

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.

Lakes, Paddle boards, Beach - Sleeps 8 Bridgton

Welcome to our little corner of Maine — a tri-level chalet on Pleasant Mountain where the mountain meets the lakes. Just 2.5 hours from Boston and under an hour from Portland, you’ll find yourself smack in the middle of some of the most beautiful lake country in New England. We’re talking Highland Lake, Long Lake, Moose Pond, Woods Pond, Kezar Lake, and Sebago — all within easy reach. And yes, the Saco River too, if tubing or paddling a lazy current sounds like your kind of afternoon.

Cabin in Paradise

Beautiful quiet and private cabin on Frye Island. Access Frye island via a 9 car ferry that runs every 15-30 minutes. Close to Portland. A beautiful 9 hole golf course with bar and grill, 15 public beaches, 2 marinas, a general store,restaurant, tennis courts, a pool, ball field, basketball court, and endless trails and roads to explore. Take bike rides to the store, catch frogs, fish for bass, play ball, and hang out at the beach! Our Bikes are included for with week long rentals.

Scenic hiking trails right outside your door

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

The Chalet~ 4 bed Lakefront Family Vacation

Welcome to your secluded slice of paradise on the shores of Sebago Lake! Nestled amidst towering pines and overlooking the tranquil waters of Seabgo Cove, our 4-bedroom waterfront chalet promises a serene escape like no other. Whether you're seeking adrenaline-pumping thrills from the local excursions, or peaceful moments surrounded by nature and a book, The Chalet offers endless opportunities for unforgettable experiences and cherished memories in the heart of Naples.

Waterhouse Family Farm Chalet

Peaceful chalet nestled beside our maple woods in Southern Maine. Upstairs queen suite TV, tea/coffee nook with books and games; first-floor cozy bedroom with full bed. One full bathroom. Open concept living room with full bed pull out couch option, dining area, all-season porch with electric fireplace, fully stocked kitchen, and washer/dryer for guest use. Hospitals, shopping and beaches about 30 minutes away. Visit our maple sugar shack just down the road!

Blueberry Hill

Beautiful property located on Watchic Lake in Standish Maine. Clear clean spring fed lake. 25 minutes to Portland with access to shopping, restaurants and entertainment. 45 minutes to North Conway New Hampshire. Where you wil find plenty of shopping, restaurants and winter skiing. Property includes use of Main Chalet home year round and two additional cabins each sleeping 4 are available from May-Oct. Great for extended families and friends.

Charming Chalet 3 min to SKIING & PVT beach access

Charming chalet with 4 bedrooms and a loft that makes it accommodating for large groups to visit! There's a full kitchen to whip up something nice & warm after a cold day on the mountain or grill up something delicious outside after a hot day at the beach!! You will find that this quaint retreat is perfect for families, couples and groups alike and has a little something to offer for all of the seasons!

Crystal Lake Chalet | Hot Tub, Sauna, Lake Access

Modern A-frame chalet with lake views, bubbling hot tub, and wood stove warmth after a day outdoors. Dog-friendly and near ski mountains, it’s ideal for family gatherings, ski weekends, and memorable winter escapes with friends. IG: @crystalaframe