Family-friendly vacation rentals in Winterport

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Winterport

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
An aerial view captures the coastal cottage set on a granite ledge beside the Penobscot River. Surrounding trees in autumn hues frame the property, and the tranquil water reflects the colorful foliage, creating a serene natural setting.
Home in Hampden
5.0 out of 5 average rating, 161 reviews

Cozy Cottage on the Penobscot – Panoramic Luxury!

Escape to your private waterfront retreat where tranquility meets luxury. Our Coastal Maine Cottage style home rests on a granite ledge that disappears twice daily with the tide. Enjoy a sun-filled interior with cherry floors, a gourmet kitchen, and a private deck for sunrise coffee or evening wine. Wake to sweeping Penobscot River views & unwind by the fire pit at river’s edge. Just 10 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

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Guest favorite
A serene lakeside view showcases a colorful sunset reflected on calm waters. Trees line the shore, creating a peaceful atmosphere amidst vibrant shades of orange and pink in the sky, with lush greenery enhancing the natural setting.
Cottage in Hermon
4.9 out of 5 average rating, 168 reviews

Modern RV on Tracy Pond

Peaceful, roomy RV in a wooded setting on Tracy Pond. All the comforts of home plus a beautiful setting in our 30 foot trailer. Full kitchen, comfy theater seating and a great WiFi connection. Fish in the lake, use the kayaks or watch the eagles soar and otters play. Enjoy the fire pit and picnic table in the great outdoors. Only 15 minutes to downtown Bangor and the airport, an hour to Acadia National Park. AirBnB's platform now adds their service fee up front , we haven't raised our price.

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Top guest favorite
A log cabin is situated on a grassy expanse beside the water, surrounded by trees displaying vibrant autumn foliage. A private dock extends into the lake, providing access for boating activities, while the spacious lawn offers plenty of room for outdoor enjoyment.
Home in Stetson
4.94 out of 5 average rating, 240 reviews

Lakefront Log Cabin on Pleasant Lake

Best view on the Lake! 500' of frontage out on a point. Private boat launch and dock site available. Covered deck to watch the sunset. Outdoor firepit, as well as indoor gas insert. Propane grill on site. Plenty of parking available. In the winter, ideal location for snowmobiling and ice-fishing. Right on to the lake and then 4 locations to get on local/ITS trails. Great fishing 200’ from the porch. Once the ice is out, hit the black crappie and Smallies from the convenience of a private launch

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Top guest favorite
A comfortable living space is complemented by large windows offering expansive views of the surrounding countryside. A gas fireplace adds warmth, and a ceiling fan provides airflow. The seating includes a leather chair and a sofa adorned with decorative pillows, set over a soft area rug.
Guesthouse in Winterport
5.0 out of 5 average rating, 123 reviews

Winterport Evergreen Farm - Guest House

Relax & enjoy a private, peaceful stay at this beautiful Christmas tree farm in Winterport. We offer the perfect spot for nature lovers and couples! Conveniently located 20 minutes from both Bangor and Belfast and 75+/- mins from Acadia National Park. After a day of adventuring on or off the property, unwind around the fire pit or on your deck. This property has woodland trails that cover 200+ acres that includes a pristine farm pond. Couples who love cooking will relish the appointed kitchen.

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Guest favorite
A living room is depicted with a light-colored sofa, flanked by two patterned armchairs. A wooden coffee table occupies the center, and a textured area rug is laid beneath. Natural light enters through sheer curtains, while wall art and a lamp enhance the cozy ambiance.
Home in Winterport
4.89 out of 5 average rating, 130 reviews

Hidden Gem

This recently renovated home is located in the heart of historic Winterport, Maine. It’s located on a quiet street with views of the Penobscot River. Winterport is an old fashion, quaint town, where everyone is very friendly. The home has three bedrooms and one bath with plenty of room to spread out. This house is so centrally located its only 52 miles to Bar Harbor and Acadia National Park, 21 miles to Belfast and 40 miles to Camden just to name a few of the beautiful coastal towns in Maine.

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Top guest favorite
The cabin is nestled among lush greenery, featuring a modern wooden exterior with multiple windows. Elevated on stilts, it harmonizes with the natural surroundings of ferns and trees, allowing for a serene atmosphere in a tranquil forest setting.
Cabin in Sedgwick
5.0 out of 5 average rating, 114 reviews

The Cabins at Currier Landing Cabin 2: Meadow

Tranquil cabin; open plan. Bedroom w/queen bed & privacy doors. Alcove w/bunkbeds. The Cabins at Currier Landing, featured in Dwell as “Three Magical Tiny Cabins Take Root in a Maine Forest,” are located on the Thos. Currier Saltwater Farm. Glimpses of water & access to 300’ of the Benjamin River Harbor shore. 2 seasonal cabins; 1 studio cabin. Centrally located on the Blue Hill Peninsula near Deer Isle, the cabins offer access to outdoor activities, cultural events, restaurants & shops.

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Superhost
Apartment in Bangor
4.83 out of 5 average rating, 189 reviews

The Phenix | DTWN Hotel *King Bed* 3rd Floor

1873 historic hotel that sits in the heart of downtown Bangor. Just steps from fantastic restaurants, breweries, & coffee shops! 1/2 mi. to amphitheater *10 minute walk* 43 mi. to Acadia Nat'l Park 3 mi. to Airport 3 min. walk to Zillman Art Museum KEY FEATURES: ☀ King-size bed w/ high end Centium Satin linens ☀ High Speed Fiber Internet ☀ 50” Roku TV w/ HULU + ☀ Desk ☀ Free Laundry in building ☀ Coffee Shop on ground floor ☀ Walking distance to Amphitheater, dining, & drinks!

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Guest favorite
A spacious white tipi is nestled among trees, with a clear view of a quiet lake. A picnic table sits nearby, accompanied by a hammock stretched between two trees, inviting relaxation in this serene natural setting.
Tent in Brooks
4.91 out of 5 average rating, 269 reviews

Waterfront Tipi Glamping // Phoenix Landing

Majestic private waterfront Tipi * on a lake. Quiet nature oasis with hot tub, woodstove, firepit, modern grill, and all the essentials. Ice skate or xc-ski across the frozen lake and watch the bald eagles fly overhead, or relax in the Adirondack chairs in front of the bonfire while you make smores and cook dinner on the grill or over the open fire, then snuggle up inside the tipi while you listen to vintage vinyl and let the owls hoot you to sleep. *Tipi closed March-April.

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Superhost
Cabin in Glenburn
4.79 out of 5 average rating, 127 reviews

Acadia Pines Cabin w/HotTub 10min2Downtown

Welcome to Acadia Pines Retreat, where the whispering pines and peaceful forest trails set the tone for your perfect Maine escape. Nestled just a short drive from Acadia National Park and the coast, this charming retreat offers the serenity of the woods with the comforts of home. * Peaceful, secluded location *Private hot spa jacuzzi to soak in after a day of hiking *Outdoor seating and stargazing spots 📍 Centrally located for day trips, lobster shacks, and scenic drives

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Top guest favorite
An outdoor movie screen is positioned by the lake, reflecting a scene from a film. Warm lights are strung around the area, enhancing the ambiance. A fire pit is visible, surrounded by a rocky edge. The tranquil water and forest backdrop provide a serene setting.
Guest suite in Orrington
4.98 out of 5 average rating, 147 reviews

Waterfront Retreat | Dock, Kayaks & Outdoor Movies

You didn’t know you needed this- until you arrived. A modern studio tucked right on the water’s edge, where nothing is between you and the lake but loons, sunlight, and time to relax. Private dock (float, fish, float again) Spa-style indoor + outdoor showers (yes, both. Why not?) Outdoor movie night under a blanket of stars Pet-friendly Swimming, stargazing, and stories you’ll be telling next year Just a short drive to town or Acadia — if you ever want to leave.

FamilyKitchenLong stay

Top guest favorite
The main living space features a modern kitchen with light wood cabinetry and dark appliances. A dining table sits center, surrounded by chairs. Large windows provide an abundance of natural light, while a cozy seating area invites relaxation. A wood stove is present for warmth during colder months.
Cabin in Jackson
4.99 out of 5 average rating, 213 reviews

Forest Cabin w/ Stunning Wall of Windows

Escape to our newly built 850 sq ft cabin in Midcoast Maine, a peaceful retreat nestled in a 30-acre forest. Perfect for up to 6 guests, this unique space features a wall of windows with forest views, just a short drive from charming coastal towns and scenic parks. Wake up to the gentle morning sun cresting over the trees, relax and breathe deeper under a star-filled sky, and witness what all four seasons have to offer. Your serene getaway awaits!

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Guest favorite
A rustic interior is visible, showcasing warm wood finishes and natural light. A dining table and chairs sit in the screened-in porch area, surrounded by greenery. The doorway leads to a cozy sleeping area, emphasizing the home's connection with nature.
Tiny home in Jackson
4.88 out of 5 average rating, 273 reviews

Tiny House oasis in Beautiful Waldo County. We❤️🐕

**JUNE PRICE DROP** We have an adorable rustic & comfy tiny house, with one queen bed. There is a fridge, tea kettle, toaster oven and stovetop. There is a daybed/couch on the porch. There is a brand new Sun Mar composting toilet in the shower house. NO INDOOR PLUMBING but we supply ample drinking/cooking/washing water and there is a sink that drains. If you have more people & your own camping equipment, look for our other listing.

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