Vacation rentals in Crooked River

4.91 out of 5 average rating, 114 reviews

An aerial view captures a secluded A-Frame nestled among dense, lush greenery. The canopy of trees surrounds the structure, providing privacy and a sense of tranquility. Sunlight filters through the leaves, creating a serene natural setting for a peaceful retreat.

Chalet in Denmark

Relaxing A-Frame with Hot Tub and 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 also! 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. Kayaks and hot tub provided! Come experience our slice of heaven for yourself, you won’t regret it!

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, 150 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, 307 reviews

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, 631 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.

4.83 out of 5 average rating, 185 reviews

Dome in Buckfield

StreamSide Getaway- HOT TUB / AC/ Wi-Fi

The Streamside Getaway offers a luxurious glamping experience in a new solar and wind-powered Geodome. Equipped with custom furniture, new hot tub,luxury appliances, free high speed wifi, AC/Heat Unit and modern bathroom and kitchen facilities, guests can enjoy a homely and comfortable stay in nature. A glamping site built in 2022 offers a contactless check-in process with a custom key code. Additionally, we have added archery, axe throwing, and kayaks to enhance your outdoor activity!

4.99 out of 5 average rating, 267 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, 144 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, 132 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.

5 out of 5 average rating, 103 reviews

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

Cabin in Norway

Hillbrook Cabin - kayak + hike, steps away!

AlexRating, 5 stars7 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. =)

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

Cabin in Naples

HotTub, Game Room, LakeFront,Paddleboards & Kayaks

EmilyRating, 5 stars1 week ago

Booked this home to accommodate 7 people. Enough space for everyone. Comfortable sleeping arrangements. Modern appliances, spacious kitchen for us all to be preparing food and drink. Enjoyed being outside by the fire pit and hot tub. Lake was peaceful and fun for us to walk down to and use kayaks and paddle boards. Great spot for a girls getaway for a couple days.

4.96 out of 5 average rating, 24 reviews

Apartment in Bridgton

The Sea Breeze-Downtown Bridgton

KateRating, 5 stars3 months ago

Beautiful place! Highly recommend!

5 out of 5 average rating, 82 reviews

A communal dining setting is depicted, with individuals gathered around a long wooden table. A large blue bucket filled with lobsters is being handled by a person wearing a plaid shirt and cap. Plates of food and bowls of salad are visible in the foreground.

Home in Harrison

Snowbird Lodge Maine

AaronRating, 5 stars5 days ago

Had a great rainy weekend here with the crew. Best equipped kitchen ever, no need to bring anything no matter what you're cooking. The sauna was roomy and oh so lovely on the rainy afternoons.

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.

4.92 out of 5 average rating, 36 reviews

A modern black cabin is situated amidst a forested area, with large windows reflecting natural surroundings. A stone pathway leads to the entrance, surrounded by landscaped rocks and greenery. Outdoor seating features nearby, providing a tranquil space to view the woods.

Home in Harrison

New modern cabin-contemporary design meets nature

AmandaRating, 5 stars2 weeks ago

Jeffrey’s place was perfect for our family. The home is peacefully secluded in the woods. It was immaculate and set up with everything we needed, including a welcome bottle of wine and a bag of local coffee! We really appreciated the baby gear too, a pack and play and high chair. We would absolutely love to stay again!