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

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

Indoor spacesKitchenBeach

5.0 out of 5 average rating, 169 reviews

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

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.

KitchenFamilyCheckout

4.9 out of 5 average rating, 139 reviews

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

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.

KitchenIndoor spacesWifi

5.0 out of 5 average rating, 129 reviews

Guest favorite

The historic home features a classic two-story facade with white siding and black accents. A large entryway with double doors is framed by a well-maintained garden, showcasing vibrant purple flowers in the foreground. Sunlight filters through the trees, casting gentle shadows on the lawn.

Apartment in Winterport

Cozy 1st Floor Studio - 1812 Pierce House

1812 Pierce House is a unique home on the National Register of Historic Places. Full of antiques & modern touches. If you like interesting places to stay, this is for you! If you like straight lines & central air, we recommend a hotel. A private entrance with your own entry hall bedroom w/ table, closet, & small hall leading to the bathroom w/ shower. Small fridge with freezer, hot water kettle, coffee/tea, 2 electric burners, toaster & microwave. Firepit in large yard. Close walk to river.

KitchenIndoor spacesLong stay

4.88 out of 5 average rating, 107 reviews

Top guest favorite

Cabin in Jackson

Forest Cabin w/ Stunning Wall of Windows

Welcome to Nadair Maine, a 30-acre forest sanctuary. Nestled here is Sunrise Cabin—a peaceful 850 sq ft retreat (for up to 6) where simplicity and beauty meet. A wall of windows frames the forest in every season, from snow-dusted pines to brilliant autumn colors. Thoughtfully prepared for your stay: cook a slow meal, unwind on the porch, or cozy up by the wood stove. Gather around the fire pit under the stars, or take a short drive to the coast. We invite you to simply arrive, breathe, and be.

KitchenIndoor spacesWifi

4.99 out of 5 average rating, 225 reviews

Guest favorite

The rustic lodge is surrounded by lush greenery, featuring a unique tower and a welcoming entrance. The exterior showcases wood shingles and large windows, inviting natural light. Flowering bushes in the foreground add a touch of greenery to the charming facade.

Home in Frankfort

Relaxing lodge in the woods

Rustic lodge nestled in the woods, on 60+ acres. Close to Bangor, coastline, and 50 miles to Bar Harbor. Large eat in dining area with plenty of room for family and friends. Outdoor fields for games, grilling, access to Maine wildlife, with plenty of parking. Private master bedroom w/bath. Large community areas to enjoy time with friends and family. At night spend time by the campfire and take in the stunning night sky. Party and events are not allowed at this time due to COVID-19 policies.

FamilyKitchenLocation

4.94 out of 5 average rating, 178 reviews

Guest favorite

A view of Tracy Pond is framed by the cottage's window. Lush trees with vibrant autumn foliage border the serene water's edge, reflecting a peaceful landscape. The clear sky above enhances the natural beauty of the secluded environment.

Cottage in Hermon

Lakefront Cottage on Tracy Pond

Lakefront cottage on 47 acre Tracy pond. The pond has no public access so it is quiet with only my home and another Air BnB on site. You share the backyard with my home. Loons, eagle, deer, otter and beaver are around. It has a fully equipped kitchen, deck and gas grill along with a stone firepit. Minutes to Bangor airport and downtown and one hour to Acadia National Park. You can swim and boat on the pond with kayaks and a canoe provided. Pets welcome but keep on leash and clean up after.

KitchenIndoor spacesWalkability

4.91 out of 5 average rating, 179 reviews

Top guest favorite

The cabin exterior features a charming combination of wood siding and dark paint, with a covered porch inviting relaxation. A small table with two chairs is positioned on the deck, overlooking a landscaped area with gravel and plants. Large windows provide natural light to the interior.

Cabin in Frankfort

Streamside Cabin at Trailhead

Enjoy some peace and quiet at this stream side cabin. This stylish little cabin is tucked away at the end of a quiet, dead end road. It is also located just steps away from historic Mount Waldo. Hike up the mountain to see beautiful vistas and a granite quarry. Put in a canoe or kayak at the public boat launch right down the road! Centrally located for travel to many coastal towns and beaches. Right off from scenic Route 1A. One hour away from Acadia National Park.

KitchenIndoor spacesComfort

4.97 out of 5 average rating, 106 reviews

Guest favorite

Home in Hampden

Cape house in Hampden

Keep it simple at this peaceful and centrally-located place. Short drive to concerts, shopping, hospitals, skiing, the coast- you name it! It's all just a short drive away. This adorable cape sits on one acre of beautiful land, complete with fruit trees and gorgeous flowers. The house, built in 1910, has the character of an old house, but was recently lovingly restored. The original wide pine floors can still be found in the two bedrooms on the second floor.

KitchenFamilyNearby

4.86 out of 5 average rating, 114 reviews

Guest favorite

A serene waterfront scene captures the vibrant hues of sunrise reflecting off calm waters. Silhouetted trees frame the view, while two canoes rest on the sandy shore, inviting exploration of the tranquil landscape.

Cabin in Hermon

Waterfront Cabin in Hermon

You’ll be surrounded by seventeen acres of tranquil trees and serene waterfront. In winter, it transforms into a picturesque wonderland, complete with snowmobile trails, ice fishing, and nearby skiing. Enjoy a variety of outdoor activities, such as kayaking and swimming, or unwind indoors with a game of pool and darts. Kayak to the three connected ponds (two of which are tucked away!) or paddle down the Souadabscook River for a chance to spot local wildlife.

FamilyKitchenValue

4.92 out of 5 average rating, 119 reviews

Top guest favorite

A spacious deck overlooks Hermon Pond, featuring a sturdy wooden table surrounded by six chairs. A grill is situated nearby. The area is decorated with an outdoor rug and shaded by large trees, creating a serene setting for gatherings.

Cabin in Hampden

Sunrise Views Cabin with King Bed, Bar & Game Room

Beautiful views of Hermon Pond from almost every window of this unique camp. There are 2 bedrooms, a king bed in master & two full/full bunk comfortable beds in the second bedroom. Newly renovated full basement combination bar & game room for your enjoyment. The large lot allows for family games while the large oak trees provides privacy. In the evenings, spark up the fire pit & roast some s'mores. A beautiful retreat to make lasting memories.

Indoor spacesKitchenValue

4.95 out of 5 average rating, 129 reviews

Top guest favorite

A modern kitchen area features gray cabinetry and a wooden countertop. Above, shelves hold neatly arranged dishes and mugs. The space is illuminated by overhead lighting, highlighting fresh flowers beside a coffee maker. A sink with a modern faucet is centrally located, enhancing functionality.

Cottage in Hampden

MaineStay Cottage #3 Full Kitchen Hampden/Bangor

NEWLY RENOVATED from top to bottom! MaineStay Cottage #3 highlights a modern farmhouse theme with touches of Maine blueberries throughout! Featuring brand new stainless steal appliances, a fully stocked kitchen, an electric fireplace, new ultra comfort bedding, fresh linens, a smart TV for streaming your favorite shows, with a charming dining area for 2, and everything you’d need for a relaxing stay - you can’t go wrong!

Indoor spacesKitchenAir conditioning

4.97 out of 5 average rating, 379 reviews