Vacation rentals in Crooked River

4.95 out of 5 average rating, 198 reviews

The farmhouse is set amidst a lush green landscape, featuring a spacious deck that wraps around part of the building. Large windows allow natural light in, while a blend of outdoor seating areas invites relaxation. The property is bordered by trees and open spaces, creating a serene environment.

Farm stay in Norway

Waterfront Home on Norway Lake - Hillcrest Farm

Serene parklike setting on 11-acres with 1,300-ft of frontage on Norway Lake. Newly renovated 1 bedroom apartment with full kitchen in historic farmhouse has separate access for complete independence. Only 35 min to Sunday River & 1 mile to downtown Norway. Direct connection to miles of hiking, biking & ski trails on Shepherd's Farm Preserve. Fish from our dock, use our canoes and kayaks, rent boats from the local marina or watch abundant wildlife from the deck - unlimited outdoor activities!

4.89 out of 5 average rating, 151 reviews

A small, wooden dock extends into Jewett Pond, featuring two teal Adirondack chairs positioned towards the water. Lush green hills rise in the background, reflecting the serene setting. The calm water invites relaxation and offers unobstructed views of the surrounding nature.

Cabin in Waterford

Jewett Pond Retreat

Relax in the Western Maine Foothills at our cabin on Jewett Pond. The main cabin has 672 sq ft of finished living space with bedroom (queen bed), bathroom, basic kitchen, great room (queen sleeper sofa), and screened porch. There is an additional rustic bunkhouse with two twin beds. This space is ideal for a couple or adventurous family who enjoys swimming, canoeing, hiking, fishing, or sitting on the screened porch with a good book and pine forest backdrop. Canoe included with booking.

4.9 out of 5 average rating, 308 reviews

Two colorful kayaks, one red and one yellow, are positioned near a serene pond surrounded by lush greenery. A picnic table is located nearby, accompanied by a hammock suspended between trees, providing an inviting space to relax in nature.

Home in Harrison

Riverfront Luxury in the woods, Million $ Views.

Secluded A-frame nestled along Crooked River, breathtaking views and world-class fly fishing beckon. Swim in the river or explore scenic hiking trails right from your doorstep. Inside, savor modern comforts including central AC. Just minutes from pristine lakes, primo golf courses, and thrilling ski slopes, this charming private oasis offers an ideal mix of tranquil relaxation and outdoor adventure. Book your unforgettable getaway today and immerse yourself in this one-of-a-kind retreat!

4.94 out of 5 average rating, 632 reviews

Loft in Bridgton

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.

4.85 out of 5 average rating, 239 reviews

Home in Waterford

Maine Lakes Region house (private hot tub)

Cozy new construction, Chalet style, year-round house, on 9 wooded acres. Lots of Privacy, Short drive to Ski slopes, snowmobile trails, hiking, or beautiful lake to swim, or kayak. Gage beach a 10-minute drive. Close to great hiking, Also Shawni peak and Sunday River. Great restaurants, Mt Washington, NH shopping outlets. Full Desk / office, 200 mb of streaming. Wi-Fi, Netflix via ROKU, Canines only, NO CATS, NO EXCEPTIONS. Portable generator in the event of a power failure provided.

4.99 out of 5 average rating, 268 reviews

Guest suite in Bridgton

Barn on Pleasant- walk to town-no cleaning fee

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 to Highland Lake, shops, and restaurants. Just minutes from Pleasant Mountain for hiking, 30 minutes from North Conway, and an hour from Portland a perfect central location to relax after exploring

4.99 out of 5 average rating, 145 reviews

A hammock is nestled between tall trees, surrounded by lush greenery. Leaves filter soft light, creating a serene atmosphere. A glimpse of water is visible through the foliage, providing a peaceful backdrop to this natural setting.

Cottage in Waterford

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. Relaxing on the dock is always an option! Enjoy the glow of the fire pit at night, or gather inside for games or a movie. Time to kickback!

4.9 out of 5 average rating, 239 reviews

A quaint cottage with a bright yellow exterior is surrounded by a snowy landscape. Large windows with dark shutters let in natural light, while a chimney extends upward from the side. The cottage features a welcoming sign displaying its name.

Cottage in Bridgton

Rustic Pebble Cottage in beautiful Bridgton, Maine

Pebble Cottage is a one hundred year old quirky camp that was enlarged some years back. It is located in Bridgton near plenty of lakes and skiing. The public beach is a short skip down the hill. The cottage is a rustic little haven that was saved from demolition, and updated with a brand new bathroom, a cute little kitchen with a dishwasher, with two heat pumps to keep the space cozy and three homey comfortable bedrooms, a large yard with a picnic table, very quiet retreat.

Place to stay in Bridgton

An outdoor patio area features a rocking chair and two colorful Adirondack chairs positioned on gravel. A natural backdrop of trees and brush creates a serene atmosphere, with wooden steps leading down to the space.

4.89 out of 5 average rating, 133 reviews

ShackHilton-New single room, privacy, deck, patio

This refurbished old shed is now a private open room with exposed beams and dry kitchen. A composting toilet is in the barn, there is no shower. There is a patio behind this room and parking to the side. There are no shared spaces in this combination of shabby-chic and rustic areas. There are views of lovely woods and grass outside the large windows. Electricity, a microwave, gravity-fed water/sink, wifi, and a keycode entry are provided.This is a glamping-style situation.

4.89 out of 5 average rating, 124 reviews

Guesthouse in Bridgton

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!

4.95 out of 5 average rating, 106 reviews

A natural trail is seen meandering through the woods, marked by a rustic wooden bridge featuring carved designs. Surrounding foliage includes a variety of green plants and fallen leaves, indicating autumn. Sunlight filters gently through the trees, creating a serene outdoor atmosphere.

Guesthouse in Greenwood

The Burrow at Patch Mountain

Surrounded by nature, this is a perfect getaway for anyone seeking an active outdoor adventure or a quiet restful retreat. The Burrow is a small studio cottage, set between two other buildings, on a wooded 4.5 acre property. It’s a peaceful, cozy space with a full size kitchen, views of the river and abundant natural light. It has its own sunny patio for eating and shares a fire ring, sitting area and driveway with my other AirBnB- The Haven at Patch Mountain

5 out of 5 average rating, 104 reviews

A modern cabin with a black exterior is surrounded by a serene winter landscape, featuring snow-covered trees and a blanket of snow on the ground. A wooden deck extends from the cabin, blending with the natural surroundings in this peaceful winter setting.

Home in Bridgton

Wren Cabin + Wood fired Sauna

We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.

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Other great vacation rentals in Crooked River

4.96 out of 5 average rating, 24 reviews

A spacious wooden deck features several adirondack chairs arranged for outdoor seating. In the background, a series of ramps lead towards colorful kayaks stored on a wooden rack, surrounded by lush greenery and trees.

Cabin in Norway

Hillbrook Cabin - kayak + hike, steps away!

AlexRating, 5 stars8 months ago

Took a family trip to see Maine during fall…this lake cabin is a bucket list dream. We enjoyed using the fire pit and also had a blast using the peddle boat on the lake. The fall foilage in October is perfect and staying in Patricia’s cabin is what dreams are made of. Thank you so much for an amazing stay. =)

4.95 out of 5 average rating, 73 reviews

A sunlit porch is displayed, featuring green trim around two large windows. Two green lounge chairs with floral cushions are positioned beside a small black table. A door leads to the interior, and a potted plant adds a touch of greenery.

Home in Harrison

Linden Tree Cottage

VictoireRating, 5 stars1 week ago

Cute cottage and fulfilled what we needed for our weekend trip. Jane is very quick to respond and was available at check-in, for if we had any issues.

5 out of 5 average rating, 3 reviews

A bright, neatly arranged bathroom features a sleek white vanity with a modern sink and a large mirror above. A toilet is positioned adjacent to the vanity, and a small trash bin sits nearby. Light-colored wooden walls and stone flooring create a clean and calming atmosphere.

Tiny home in Casco

The Casco Tiny house!

MaliaRating, 5 stars3 months ago

Cody is the greatest host. He was very genuine, and responsive with everything. This little home will be one to remember. It was very comfortable and peaceful. I would come back again! 😊🙏🏽

4.96 out of 5 average rating, 26 reviews

The open living and dining area features a large wooden table surrounded by black chairs. Natural light enters through multiple windows, highlighting the wooden ceiling and floor. A staircase spirals to the upper level, while a cozy seating arrangement is found near the fireplace.

Cottage in Bridgton

Lake Front Cabin on Desirable Highland Lake

DougRating, 5 stars2 weeks ago

My wife and I stayed at John's place for a quick weekend trip but the house is large enough for several more with 5 additional beds plus some space in the living room for sleeping. Great location on the lake with amazing views and only about a mile and a half from downtown Bridgton with some shops and nice restaurants. The house was immaculate and had everything you need from kitchen accessories to towels to plenty of games and books. John was extremely responsive and I don't think I waited more than 30 minutes for the few back and forth messages we had. Definitely recommend!

4.95 out of 5 average rating, 42 reviews

A modern lake house features a spacious deck with outdoor dining seating and a grill, surrounded by lush greenery. Large windows allow natural light to brighten the interior, while a gravel path leads to the grassy area below.

Home in Bridgton

Stunning Bridgton Lake House with EV charger

LimorRating, 5 stars3 months ago

Beautiful and comfortable house in a lovely natural setting, five minutes from Pleasant Mountain, which we think is a wonderful family ski area. Marty was very kind and extremely helpful with all our questions and requests. We would love to return and experience other seasons here as well.

4.95 out of 5 average rating, 22 reviews

A covered front porch features wooden beams and a railing, providing a serene space surrounded by green foliage. Two wooden chairs and a small table create a cozy seating area, complemented by hanging ferns for a touch of nature.

Cabin in Norway

Oliver's Outlook

DennisRating, 5 stars3 weeks ago

Nice place. Clean and well organized. A great place to stay

5 out of 5 average rating, 3 reviews

An indoor recreational area showcases a ping pong table at the forefront, flanked by seating options. Vibrant posters adorn the walls, with a disco ball suspended from the ceiling. Traditional arcade machines and decorative lighting provide a lively atmosphere.

Home in Bridgton

Ell Suite walk to town beach

HenryRating, 5 stars4 days ago

place was bigger than expected . all the towels were high quality and seemed brand new as well. would most definitely come back again