Chalet vacation rentals in Cumberland County

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Top-rated chalet rentals in Cumberland County

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A multi-level cabin is set amidst lush greenery, featuring an elevated deck and a large screened porch. Stairs lead up from the ground level to the welcoming main entry. The natural setting provides a serene backdrop, enhancing the cabin's rustic charm.

Chalet in Bridgton

4.9 out of 5 average rating, 48 reviews

5 bedroom home, 5 minutes from the lake or skiing

Enjoy our home! (2) family bedrooms with custom made king size bed & child size extra small twin bunks in same space as kings, (2) rooms with queen beds, & (1) room with twin bed. Spacious living &dining room.3 season porch.2 full bathrooms.1st floor sitting area, laundry & playroom. 5 mins. toPleasant mtn skiing, Moose Pond, Sabatis Island, rentals& boat launch. 10 mins. to center shops, movies & restaurants.15 mins to Fryeburg.25 minutes to N. Conway shops.Lots of local fun spots in between!

Guest favorite

A custom log cabin is showcased with a robust wooden structure and large arched windows. The building is elevated on a snow-covered landscape, surrounded by natural stone steps and trees, offering a rustic appearance in harmony with the mountain setting.

Chalet in Bridgton

4.92 out of 5 average rating, 12 reviews

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.

A chalet-style exterior is depicted, showcasing a slanted green roof and wooden porch. A gravel driveway leads to the entrance, surrounded by well-maintained landscaping featuring shrubs and small trees. Natural light illuminates the scene under a clear blue sky.

Chalet in Bridgton

4.67 out of 5 average rating, 3 reviews

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.

Guest favorite

The A-Frame cabin features a striking black exterior accentuated by bright yellow trim. A large umbrella shades a wooden deck with seating, inviting relaxation. Surrounding trees create a serene atmosphere, enhancing the cabin's secluded charm within the natural landscape.

Chalet in Denmark

4.91 out of 5 average rating, 145 reviews

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!

Guest favorite

A warm kitchen area features a central island surrounded by black chairs. A wooden dining table with matching benches sits nearby. Large windows let in natural light and showcase the greenery outside, while wood paneling adds a rustic charm to the space.

Chalet in Bridgton

5 out of 5 average rating, 35 reviews

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

Top guest favorite

A cozy fire pit area is situated near the water's edge, surrounded by tall trees. Adjacently, five colorful adirondack chairs offer seating for gatherings. A serene view of the lake and a private dock can be seen in the background, providing a tranquil backdrop.

Chalet in Naples

4.97 out of 5 average rating, 118 reviews

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.

Top guest favorite

A relaxing outdoor area is shown, featuring several seating options around a fire pit. Two cabins can be seen, with one situated on a hill and the other by the water. A sun umbrella provides shade, surrounded by trees and nature.

Chalet in Standish

4.96 out of 5 average rating, 245 reviews

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.

Guest favorite

Chalet in Bridgton

5 out of 5 average rating, 12 reviews

SKI IN/OUT Pleasant Mountain 3* bedrooms 2.5 baths

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

Guest favorite

A spacious living area features warm wood paneling and a cozy wooden fireplace. Comfortable seating is arranged around a coffee table, and large glass doors allow natural light to fill the room, leading to the scenic outdoors. A ladder provides access to the loft area.

Chalet in Bridgton

4.86 out of 5 average rating, 123 reviews

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!