Family-friendly holiday rentals in Winslow

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Sweet Retreat: 3 BDR Stylish Home Mins To Colby

Stay in the heart of Maine - Vacationland! This spacious 1,200 sq. ft. ground-floor home is just 1.1 miles from I-95, making it an ideal base for exploring our beautiful state. We're about 1 hour from Portland and 1.5 hours from Bar Harbor & Acadia National Park. Enjoy the perfect blend of modern comfort and rustic charm in this inviting two-family home. As a bonus, guests have access to a private backyard featuring a patio set, fire pit, garden, fenced area, and mature trees for added privacy.

Kitchen · Indoor spaces · Location

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Off-Grid Cabin with Wood Fired Hot Tub. 4 Kayaks

Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- beautiful swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Family · Kitchen · Hot tub

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Guest favourite

Lakefront 3 bedroom pet friendly on Messalonski

Make memories of a lifetime at this unique and cozy family-pet-friendly private lakefront on Messalonskee. Beautifully manicured lawn/gardens with a fire pit surrounded by the peaceful sounds of nature. A large dock to take in the spectacular views of bald eagles, loons, and blue herons. Owners boat is attached for occasional boat rides. This guesthouse is newly built with a covered porch overlooking the serene lake. Comes w/3 kayaks, 2 paddle boards, a paddle boat, life jackets, and a canoe

Indoor spaces · Kitchen · Heating

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Guest favourite

Farm house, River, Island, animals & private Chef.

MARCH-APRIL DAILY. Medicine Hill is a 136 acre farm on the Sandy River complete with a swimming hole and an entire island to explore. We grow vegetables, herbs & flowers. Our animals include sheep, chickens & rabbits. You will have full access to all areas of the farm! Spend time fishing or relaxing on the river. Or literally just sitting on the porch unwinding and taking it all in. 4 private bedrooms have stunning views surrounded by trees or fields. And if the Chef is available..EAT!!!

Kitchen · Indoor spaces · Sleep quality

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Guest favourite

Carriage House

Renovated circa 1920 carriage house in a quaint New England college town. Eight-minute walk to busy downtown with restaurants, bars, shops, and grocery store. Elegant contemporary style. Open concept downstairs with sofa, daybed (napping in the sun!), and chef-designed kitchen. Second level with two queen beds and small balcony. Adjoins miles of walking trails and forest, full of wildlife. Less than 5-minute drive to a 1.5 mile running trail along the Sandy River, with refreshing swimming.

Indoor spaces · Family · Long stay

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Sister a-frame in Woods (A)

Escape to one of our two sister A frames. These cozy cottages are nestled in the Oakland, Maine woods. Close proximity to I-95, Messalonskee and prestigious Belgrade Lakes you will find home to a wide variety of wildlife and nature. Boating, fishing and ATV riding close by! The campus includes a loft with a view, walking trail, free/overflow parking. A luxury, campy feel makes this a perfect getaway for you and your family. Check out our other listings managed by Hall’s Homes RE online!

Indoor spaces · Kitchen · Parking

Cozy House in Waterville

Our private Cozy House has just been renovated! We put in a new kitchen, bathroom, laundry room, and a big 4k smart tv/Apple TV. It's in a friendly neighborhood located in the heart of Waterville only five minutes from Colby College, Thomas College (by car) and just a few minutes from downtown Waterville. Everything is very close to our location. There's a Hannafords nearby, Maine General Hospital and many restaurants, schools and stores. We are located on a private dead-end driveway .

Indoor spaces · Kitchen · Bathroom

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Guest favourite

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

Family · Indoor spaces · Cleanliness

Lakeside retreat on quiet cove on Cobbessee Lake!

Nothing beats summer days on the lake in Maine. Not only is this lake home situated on a quiet cove on central Maine's Cobbossee Lake, but it is near amenities in Augusta and close to I-95! Enjoy two large docks, a large lawn and gently sloping swimming area, and a newly renovated five bedroom house with two full bathrooms. This is the Maine vacation home you are looking for! Two of the bedrooms and one bathroom are in the basement, which is still under some small construction.

Family · Indoor spaces · Cleanliness

Brook Ridge Retreat

Work, play, & relax at Brook Ridge Retreat! Come visit your Colby or Thomas College student and have the comforts of home. Do some grilling or cook up a favorite meal in the full kitchen. Remotely connect to work or school at our custom-made desk and dedicated office area with wireless printer and available computer monitor. Splash in the brook or in the basin, and sit under the waterfalls. WiFi, firepit, Keurig or french press, electric fireplace, large decks, & big yard.

Family · Kitchen · Laundry

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Guest favourite

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Family · Kitchen · Hospitality

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Guest favourite

Sterling House

1960’s Cape in a quiet, centrally located neighborhood. We are licensed with the City of Waterville as a STR. Sleeps (7) comfortably. Less than two miles to Waterville’s Downtown area with several restaurants and bars, Waterville Opera House, Colby College, Thomas College as well as MaineGeneral Thayer Hospital. We are a pet-free home with NO central A/C - fans only. Landscaping: We have a lawn service every other Wednesday between 7:30am and 9am.

Kitchen · Family · Heating