
Holiday houses in Crooked River
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Top-rated holiday rentals in Crooked River
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Privacy, River, Pond, A frame Hot Tub, EPIC Views,
14 Acres Secluded A-frame nestled along Clean Crooked River, Hot tub with breathtaking VIEWS and world-class fishing. Swim in the river, private pond or explore hiking trails right from your door. Central AC - Gas Fireplace - Modern Kitchen. 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. Invite a private chef, florist or yoga teacher to fully unwind. Heated bath floors.
4.9 out of 5 average rating, 365 reviews
Waterfront,Hot tub,Private dock,Freshly renovated
Welcome to the freshly renovated Cabin on a Moose Pond!Nestled near the hills of Pleasant Mountain.Enjoy a day at the lake fishing,swimming,skiing,hiking or snowmobiling. In the evening,relax in the new hot tub,watch a movie on the home theater or challenge friends to video games.End your day by the campfire making s’mores by the pond. Spend a lazy day on the hammock or take a day trip to explore regional attractions in beautiful ME and NH. For your safety, the area is under video surveillance.
4.82 out of 5 average rating, 191 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
5.0 out of 5 average rating, 13 reviews
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!
4.94 out of 5 average rating, 245 reviews
Lake Front Cabin on Desirable Highland Lake
Escape to this lakefront cabin in Bridgton, Maine—your four-season retreat. Summer: Live the lake life! Enjoy our 15 ft private sandy beach, swim in the crystal-clear water, and use our canoe and kayak for sunset paddles. Fall: This is the time for cozy relaxation. Take in stunning foliage views, go hiking or apple picking, and end the day gathered around the fire pit. Winter: Experience a snow-filled wonderland. Ski, snowshoe, or cross-country ski, then come home to a warm, inviting cabin.
4.98 out of 5 average rating, 64 reviews
The Modern Lakehouse
This modern lakehouse is situated on Hogan Pond in Oxford Maine. Here you can stay with all the comforts of a beautiful lakehouse built in 2020 while being feet from the water. This is a great place to vacation whether you prefer the private sandy beach, the A/C inside complete with Smart TV cable and Wifi, or the hottub! Sip a drink at the bar while watching the game or use the grill on the deck but be sure to use the built in sound system to play your music throughout the house and deck.
5.0 out of 5 average rating, 246 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.
4.94 out of 5 average rating, 725 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.
4.85 out of 5 average rating, 253 reviews
Mirror Pond Cottage
A sweet space on a pond, this cottage is perfect for those looking for a quiet getaway. We offer swimming, kayaks and a canoe, life jackets along with a raft to float on. Endless fun in the water, with no motors to be heard. This is a quiet spot and we would hate to be responsible for ruining that. We are family friendly and kids are welcome, but please leave the party at the casino (5 minutes away)! The waterfront is sandy and shallow, perfect for young ones to splash around in.
4.92 out of 5 average rating, 149 reviews
The Woods Maine | A Luxury Treehouse Experience
The Woods is a quintessential New England-style home in the trees. Private, secluded, and effortlessly livable if you never want to leave. Located 1 hour from Portland, Maine and 3 hours from Boston. The Woods is located in beautiful Norway, Maine, tucked away from the coast in a rustic, woodsy, good-vibes-only kind of place. Soak in the fresh mountain air, pristine lakes, and vibrant, changing seasons from your home among the trees. Social Media: @thewoodsmaine @thewoodsmaineshop
5.0 out of 5 average rating, 17 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.
4.99 out of 5 average rating, 70 reviews
FALL Lakefront Getaway Cabin/Private Sandy Beach!
OCT DATES AVAILABLE! Paddle, fish & swim from your own sandy beach in this beautiful private cove on a very quiet lake. Watch the loons and sunset across this 1 mile long, 248 acre, spring fed slice of heaven. Mountain and lake views from the bedroom, screened porch, and living room. Conveniently located: 50 miles to Portland Jetport, 26 miles to North Conway, NH, and 15 minutes to Bridgton with breweries, shopping, and dining.
4.98 out of 5 average rating, 53 reviewsPopular amenities for Crooked River holiday rentals
Other great holiday rentals in Crooked River

Norway Chalet – Lake & Ski + Hot Tub & Game Room
4.98 out of 5 average rating, 86 reviews
Long Lake Happiness-Waterfront/Dock/Kayaks
4.88 out of 5 average rating, 24 reviews
Home Away from Home with Mountain Views
5.0 out of 5 average rating, 53 reviews
Stunning Bridgton Lake House with EV charger
4.96 out of 5 average rating, 67 reviews
Lakehouse only 70 feet from water!
4.95 out of 5 average rating, 80 reviews
Water's Edge in Norway, Maine
4.94 out of 5 average rating, 53 reviews
Vacationland Retreat Lake House
5.0 out of 5 average rating, 22 reviews
Lake Front 3 Season House with Private Deck
4.93 out of 5 average rating, 28 reviewsDestinations to explore
- Sebago Lake
- Story Land
- Loon Mountain Resort
- Willard Beach
- Scarborough Beach
- Mount Washington Cog Railway
- Santa's Village
- Sunday River Resort
- Cranmore Mountain Resort
- Hills Beach
- East End Beach
- Pleasant Mountain Ski Area
- Omni Mount Washington Resort
- Conway Scenic Railroad
- Wolfe's Neck Woods State Park
- Attitash Mountain Resort
- Crescent Beach State Park
- Echo Lake State Park
- Crawford Notch State Park
- Diana's Baths
- Waterville Valley Resort
- Flume Gorge
- Funtown Splashtown USA
- Palace Playland





