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
Home in Bridgton
5.0 out of 5 average rating, 8 reviews

Long Lake-Lake Front | 1.6 Acre Peninsula

Attention Boaters & Skiers! Stunning , 4-bedroom, 2-bathroom new lake house on Long Lake. Set on a private 1.6-acre peninsula with 670 ft of waterfront, panoramic lake views and direct access to Long Lake, Brandy Pond, and Big Sebago Lake from your private dock. 15 minutes to Pleasant Mountain; Nearby Gunstock & Wildcat!! Full kitchen, Blackstone grill,fire , and a bar/game room. Private yet close to downtown Bridgton and Harrison. High-end finishes throughout! - 1 mile from Bridgton Academy

Top Guest favourite
Cabin in Norway
5.0 out of 5 average rating, 98 reviews

Secluded 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
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, 259 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 hot tub is positioned on a spacious deck, offering a stunning view of a mountain during sunset. The scenery features a blend of warm hues in the sky, with gentle slopes visible in the background. Steps lead up to the hot tub, enhancing accessibility.
Home in Bridgton
4.95 out of 5 average rating, 169 reviews

*1MMview*Bar,Hot Tub,3mins2Pleasant Mnt, Pool tab.

This special, completely renovated place can host your family gathering or group of friends in an inviting setting. This unique house with a private bar, spa, and a pool table will satisfy all your vacation needs! Located close to everything, but absolutely quite and private 20 acres property! It is situated on a ridge with a spectacular mountain view. Our house offers comfort & entertainment. The property will give you the full vacation in the woods experience. This is just what you need!

Guest favourite
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
4.92 out of 5 average rating, 59 reviews

New modern cabin-contemporary design meets nature

New construction, steps away from Crystal Lake in Harrison, ME. There is access to the Crystal Heights Association waterfront w/ private parking available, 1 mile from Crystal & Long Lake boat launches. Close to restaurants & shopping in Harrison Village & Downtown Bridgton. We are a short distance to Pleasant Mountain & Sunday River Ski Resorts. There is nearby hiking w/ amazing views at Hawk Mountain. This is a perfect nature getaway for small groups or wedding guests from nearby venues.

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
4.94 out of 5 average rating, 714 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
An aerial view showcases a spacious home surrounded by lush greenery and a golf course. Nearby, a parking area is visible, along with manicured fairways and trees in the distance, providing a sense of tranquility and openness.
Home in Bridgton
4.95 out of 5 average rating, 112 reviews

Beautiful Views, Bridgton Maine

Vacation getaway for all seasons. Enjoy mountain and golf course views from this 3,800 square foot home. Pleasant Mountain Ski Area beckons from 10 minutes away. Sunday River Ski Area is 40 minutes away. Or bring your clubs and test your skills on the challenging 18 holes at Bridgton Highlands Golf located steps away. At the end of the day, sip on an adult beverage in the spacious timber frame great room and marvel at the field-stone fireplace that stretches from floor to the ceiling.

Top Guest favourite
The image showcases a bright interior with vaulted ceilings, featuring large angular windows that allow natural light to fill the space. A rustic brick fireplace with a black stove is centered against a wall. A wooden ceiling fan hangs above, enhancing the cabin-like atmosphere.
Home in Waterford
4.85 out of 5 average rating, 251 reviews

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.

Top Guest favourite
A modern kitchen features sleek countertops and high-end appliances, including a stainless steel oven and range. Black pendant lights hang above a spacious island with bar stools. Multiple windows allow for abundant natural light, with a patterned rug adding warmth to the wooden floors.
Guesthouse in Hiram
5.0 out of 5 average rating, 135 reviews

1BR cozy, luxurious getaway @ Krista's Guesthouse

Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

Top Guest favourite
Treehouse in Pownal
4.99 out of 5 average rating, 183 reviews

The Copper Fox Treehouse

Named the 10th most spectacular tree house in the world by the BBC Featured in the book: Modern Tree Houses by Taschen Airbnb's Most wishlisted property in Maine in 2025! Come experience the whimsy and craftsmanship of this red fox head shaped treehouse for yourself. The magic of this wild adventure awaits you in the treetops... Come to relax, explore and make lasting memories your family and friends will talk about for years. Follow our journey on IG at @thecopperfoxtreehouse

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
4.99 out of 5 average rating, 68 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.

Top Guest favourite
Cabin in Harrison
4.94 out of 5 average rating, 32 reviews

Classic Lakefront Cabin · Dock, Kayaks & Fire Pit

Wake up to still water and the sound of loons. This 3-bedroom cabin sits right on Crystal Lake in Harrison, Maine - one of the cleanest, most peaceful lakes in the region. Step outside and you’re on the water, it’s that simple. Days are spent swimming or kayaking, and evenings end around the fire pit watching the sun fall behind the trees. Everything you need is here, and nothing you don’t. Bridgton: 10 min · Naples: 15 min · Portland: 1 hr · Boston: 2.5 hrs

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