Holiday houses in Crooked River

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Top-rated holiday rentals in Crooked River

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A two-story cottage features a rustic wooden exterior, surrounded by trees and greenery. A welcoming porch with a wooden bench and potted flowers invites relaxation, while a grassy area offers space for outdoor activities. The structure is harmoniously integrated into the natural environment.
Guesthouse in Bridgton
4.94 out of 5 average rating, 33 reviews

The Pot Shed at Round House Farm

Immerse yourself in the beauty of Maine from the comfort of our two story cottage finished in reclaimed wood and furnishings inspired by the French countryside. The Pot Shed, formerly my grandmother’s garden shop, is a historic building reimagined as a guest house on our backyard horse farm. The screen porch and deck alongside our woodland paddock, with attached outdoor hot shower and outhouse with composting toilet, make it the perfect place to get back to nature. Base your next adventure here!

Top Guest favourite
Cabin in Norway
5 out of 5 average rating, 93 reviews

Modern Cabin: View, Hot Tub, 10 min Walk to Lake

Architect-designed alpine cabin with panoramic White Mountain views, including Mount Washington Relax in the hot tub, watch the sunset over the mountains, and enjoy a peaceful forest setting close to lakes, hiking trails, and skiing. 4WD or AWD REQUIRED Nov 1st-April 15th Starting May–Fall 2026, there may occasionally be (weekday only) construction noise up the road (250ft) from neighbors building their home. Work would occur roughly 8am–4/5pm and not every day. Cannot see it from the house.

Top Guest favourite
Cabin in Norway
4.98 out of 5 average rating, 42 reviews

Frost Hill Schoolhouse

Nestled on a quiet dirt road in the woods of Norway Maine sits Frost Hill Schoolhouse. Formerly a one room schoolhouse in use until the 1930s. Come enjoy the peace & solitude of Maine’s lakes & mountains region while staying in a piece of Maine’s history. Although small, the house is filled with antiques collected around New England & is carefully curated with a charming & colorful Scandinavian inspired design. Just minutes away from Norway lake, 30 minutes to Sebago Lake & an hour to Portland.

Guest favourite
A private hot tub is surrounded by trees displaying vibrant autumn leaves, with a gentle stream flowing nearby. A fire pit sits beside the hot tub, offering a cozy gathering space. The cabin's exterior features wooden siding and large windows that invite natural light.
Tiny home in Norway
4.94 out of 5 average rating, 254 reviews

Glass Wall Waterfront Hot Tub Fireplace Tiny Home

Wake up to rushing waterfalls right outside your glass wall in this romantic waterfront tiny home in Norway, Maine! Private hot tub with river views, see-through gas fireplace, cozy raised queen bed overlooking the water, outdoor shower, hammocks, and direct access to hiking trails. Total privacy—no neighbors in sight. Modern kitchen, heated floors, fast WiFi, and thoughtful touches for couples or solo escapes. Romantic getaway near Sunday River skiing, golf & Maine adventures. Nature's oasis

Top Guest favourite
A spacious bedroom is highlighted by a king-size bed adorned with subtle patterns. Natural light pours in through large windows, illuminating the beautiful stone fireplace, which provides a cozy focal point. A comfortable reclining couch sits nearby, enhancing the relaxing atmosphere.
Guest suite in Bridgton
4.98 out of 5 average rating, 365 reviews

Barn on Pleasant- Walk to Highland Beach

Welcome to our charming loft in a peaceful neighborhood, ideal for comfort and convenience. This well-maintained property provides a cozy living space. The loft features a kitchenette, a beautiful stone fireplace and a big, comfy reclining couch. Visit Bridgton this summer walking distance highland lake, shops, and restaurants. Just minutes from Pleasant Mountain for hiking, skiing, 30 minutes from North Conway, and an hour from Portland a perfect central location to relax after exploring.

Top Guest favourite
A spacious living area is highlighted by hardwood floors and tall ceilings with exposed beams. Large windows allow natural light to fill the room, illuminating the comfortable seating, modern coffee table, and decorative lamps. A piece of wall art adds a touch of character.
Loft in Bridgton
4.95 out of 5 average rating, 710 reviews

Tap House Loft~Sunny & Spacious, Private Hot Tub

Conveniently located in the heart of Downtown Bridgton, the Tap House Loft is ready for you, your friends and your family to enjoy! Walk to vibrant Main Street, Pondicherry Park, the Magic Lantern Theater, Highland Lake and all the downtown shops, gallerias and restaurants...or simply relax in the peace and quiet of our newly restored, historic warehouse. Located above the Sundown Lounge, this 900 sq ft space offers a large Master Suite with French Doors leading to a deck and hot tub.

Top Guest favourite
A cozy interior features natural wood paneling and beams. Two upholstered chairs are positioned near a large window, allowing light to fill the space. A small bookshelf holds several books, while kitchenware is organized on a nearby shelf. A white stove complements the rustic setting.
Cabin in Bridgton
4.95 out of 5 average rating, 189 reviews

Writers Cabin in the Woods with Sauna!

Nestled in the woods and on Adams Pond with new wood fired sauna! The cabin feels totally hidden away but is less than 10 minutes to Bridgton and Naples, hiking, beaches and restaurants. The woods are beautiful and peaceful and the pond is just down a mossy path. Great for couples or a weekend away. Large deck with grill and outdoor shower, firepit. There is a shared dock on the pond for swimming, fishing, or just enjoying the view as well as a canoe and 2 kayaks, and a paddle board.

Guest favourite
A modern exterior of the eco-friendly retreat is displayed, showcasing a sloped roof and large windows. The deck features comfortable seating and steps leading to the welcoming entryway. Surrounding greenery adds a natural backdrop, enhancing the serene atmosphere of the waterfront sanctuary.
Home in Sweden
4.97 out of 5 average rating, 138 reviews

Waterfront| Outdoor Sauna| Ski| Mountains| Firepit

Escape to Camp Sweden, an eco-friendly waterfront sanctuary in the foothills of the White Mountains. Paddle across the private pond, go for a hike in the Mountains nearby, or jump in the new outdoor panoramic barrel sauna and let your worries evaporate away. Enjoy a unique and rejuvenating experience that connects you to nature without sacrificing comfort. This retreat offers all-season enjoyment for nature lovers and outdoor enthusiasts alike. Experience Maine’s beauty today

Superhost
The image captures a lush green landscape in front of a charming red building. A winding drive leads towards the residence, while mountains rise in the background under a partly cloudy sky. Colorful flowers and greenery frame the scene, enhancing its natural beauty.
Guesthouse in Bridgton
4.82 out of 5 average rating, 166 reviews

Private apart with luxury view, mins to everything

Welcome to the Peak View Apartment! This lovely and stylish place is perfect for a honeymoon, anniversary or romantic getaway or for those who crave for retreat. This is what you imagine when you want to relax in the house in the mountains!!! But also great for a small family with kids! Sitting on the ridge of Pleasant Mountain, the place is minutes away from all the attractions and beautiful lakes. The property will give you the full vacation in the woods experience!

Top Guest favourite
A spacious great room features vaulted ceilings with triangular windows allowing natural light to fill the space. A cozy sofa and chairs are arranged near a wood-burning stove, while double glass doors open to a deck with seating and views of the surrounding landscape.
Cabin in Norway
4.98 out of 5 average rating, 65 reviews

The Cloud Cabin

Escape to your Magical Maine Mountain Experience. Whether from the deck, the cozy plum great-room sofa, or the library loft, experience the feeling of living in the clouds, and overlooking the beautiful White Mountains in our ultra-private and remote slice of heaven. Locally hand-built in 2024, the Cloud Cabin represents the thoughtful combination of luxury mountain design, cozy homey comfort, and top-quality everything. 24/7 Remote Concierge Service included.

Guest favourite
A hammock is suspended between two trees, facing the serene waters of Norway Lake. Lush greenery surrounds the area, with a view of the lake's gently rippling surface under a soft sky. The peaceful setting invites relaxation and tranquility.
Cottage in Norway
4.9 out of 5 average rating, 20 reviews

Peaceful 3br lakefront w floating picnic table

This adorable camp is located directly on Norway Lake, with 100 feet feet of water frontage. Whether you prefer wading into the water or jumping off the dock into deep water, this is the place for you. Spend your vacation relaxing in the hammock, drinking coffee on the 3 season porch, fishing, kayaking, playing yard games, watching the sunset from the floating picnic table at the dock, and cozying up around the Solo Stove campfire.

Top Guest favourite
Tall trees frame a serene pond, with calm waters reflecting the surrounding greenery. The landscape features gentle hills in the background, adding depth to the natural setting. Soft sunlight filters through the leaves, creating a peaceful ambiance by the water's edge.
Cottage in Waterford
4.99 out of 5 average rating, 178 reviews

Tall Pines Hideaway

Classic Maine cottage on Papoose Pond, nestled among the trees. Enjoy the peace and quiet of this small pond, whether reading a book, or paddling a kayak, canoe or paddleboard. All the equipment is waiting for you. Lots to explore in the area as well, being close to Bethel and Sunday River, Fryeburg, North Conway and the White Mountains. Enjoy the glow of the fire pit at night, or gather inside for games or a movie.

Popular amenities for Crooked River holiday rentals

  1. Airbnb
  2. United States
  3. Maine
  4. Crooked River