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.

1 of 1 pages1 / 1

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 spacesKitchenRiver

5.0 out of 5 average rating, 163 reviews

Top guest favorite

Home in Stockton Springs

Private Beach, Bar Harbor, Acadia, 15 beds, Pets

" Memories that will last a lifetime". Discover The Retreat House, a charming Waterfront Maine haven near Bar Harbor and Acadia. Unlike typical rentals, our property offers a private beach and stunning water views while being pet-friendly. The House is designed to meet the needs of multi-generational families and larger groups, providing ample space for unforgettable vacation moments. Enjoy beach bonfires, whale watching, lobster bakes, and swimming. Be sure to view the 200+ photos, then book.

Indoor spacesFamilyGrill

4.91 out of 5 average rating, 111 reviews

Top guest favorite

A wooden dock extends into a calm lake, framed by distant hills and clear skies. The water's surface reflects the surroundings, creating a serene and tranquil atmosphere.

Home in Orland

Private Lakefront Cottage Close to Bar Harbor

Newly renovated historic lakefront home on 8 acres with a lot of privacy. Conveniently located only 20 minutes from airport, this 2-story cedarshake home sits on the water's edge and is close to Bar Harbor and surrounding picturesque towns for shopping, restaurants and sightseeing. Large wrap-around porch (with dining table that seats 10 and several comfy seating areas) for family fun & outdoor dining. Large deck, perfect for swimming, lake fun and canoe rides. AC and heats in upstairs bedrooms.

FamilyIndoor spacesSleep quality

4.98 out of 5 average rating, 127 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.

Indoor spacesKitchenView

4.9 out of 5 average rating, 135 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.

FamilyKitchenNearby

5.0 out of 5 average rating, 125 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.

Indoor spacesKitchenDecor

4.88 out of 5 average rating, 101 reviews

Top guest favorite

The image captures a serene view of the water at sunset, with the sun reflecting on the surface. Framed by lush green foliage, a small rustic bench is positioned on the shore, inviting quiet moments of contemplation.

Cottage in Belfast

Quiet cottage on the bay

Settle in at this mid-coast Maine treasure, where you will find more than you hoped for in a getaway. Located in a private neighborhood and setback on a private road on 2.5 acres. You can take a short stroll down a wooded path to the Belfast bay and watch the sunset or simply enjoy the view from living room. The rocky beach gives you access to a wonderful piece of the Maine coastline. Come make some memories at this unique, pet and family-friendly quiet cottage just 1 mile to downtown Belfast.

KitchenIndoor spacesGetting around

4.98 out of 5 average rating, 212 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.

FamilyIndoor spacesBathroom

4.94 out of 5 average rating, 178 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.

FamilyIndoor spacesHospitality

4.98 out of 5 average rating, 102 reviews

Top 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.

Indoor spacesKitchenView

4.86 out of 5 average rating, 111 reviews

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

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!

KitchenFamilyBreakfast

4.99 out of 5 average rating, 221 reviews

Guest favorite

A vibrant sunset is reflected on the calm waters of Graham Lake, with streaks of orange, pink, and purple filling the sky. Silhouettes of distant hills and trees frame the scene, creating a serene atmosphere perfect for relaxation.

Cottage in Waltham

Quiet lakefront cottage on Graham Lake

Waterfront cottage on quiet Graham lake in the middle of our small working farm. Great spot for quiet relaxation, fishing or kayaking. 2 canoes on the property. Good central location for visiting Bangor, Bar Harbor, Acadia National Park and Downeast Sunrise ATV Trail. Private setting. Wifi available at the farmhouse. Because of family allergies, we cannot host pets

KitchenIndoor spacesQuiet

4.95 out of 5 average rating, 912 reviews