Family-friendly vacation rentals in Woolwich

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Woolwich

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

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Guest favorite

Guesthouse in South Bristol

4.98 out of 5 average rating, 379 reviews

Waterfront Guest House on the Maine Coast

Bright open four-season guest house with fantastic view of Jones Cove and the open ocean in beautiful South Bristol, Maine. The guest house offers privacy and independence. The top floor has an open space with kitchen, sleeping area with queen bed, bathroom. The ground floor has a desk, Smart TV, seating area and French doors that open onto a stone patio. Includes Kohler generator, fiber optic wifi, outdoor grill & fire pit. The water is tidal Owner lives on property (150 ft from guest house)

Guest favorite

Rental unit in Edgecomb

4.91 out of 5 average rating, 322 reviews

Sunny Apt in Woods 10 Min to 3 Towns- Dog Friendly

Bright, cozy apartment, surrounded by deep woods, completely separate from our home, w/ its own entrance, yet we are available if you need us. Located between Boothbay, Damariscotta, & Wiscasset, 1 mile from Route 1 and 27, on 13 acres, abutting 100s of acres of preserve land - provides the best of both worlds - peaceful woods, but less than 15 minutes from restaurants, shops & activities, plus, dedicated WiFi /2 Smart TVs. While dogs are welcome we can’t host feline guests due to allergies.

Guest favorite

Farm stay in Westport Island

4.83 out of 5 average rating, 124 reviews

Westport Island Stilt House

Once the island Trading Post (in the 1820's) now serves as a private retreat on Westport Island. The whole property has been listed on the National Register of Historic Places since 1982. The building is nestled at the water's edge, half on land and half on stilts over the tidal waters of the Sheepscot River. The property has its own private deck, island, rocky beach, trails and hammock. This is an old structure - over 200 years old! A great piece of history and an absolute oasis.

Guest favorite

Home in Bath

4.9 out of 5 average rating, 319 reviews

Gorgeous Winter Studio on the Kennebec

Gorgeous riverside studio, the smaller of two AirBnB houses on the same property on the outskirts of beautiful and historic Bath, Maine. (The other, “Beautiful Summer River Retreat,” is a separate Airbnb rental.) Kitchenette, bathroom/shower, living room, and bedroom. Simple, modern decor. Close to great shops, restaurants, and beaches, and just a 20-minute drive from Bowdoin College. Adjacent to a boat launch, and a short walk from the Bath Marine Museum and a scenic dog park.

Guest favorite

Rental unit in Lisbon falls

4.95 out of 5 average rating, 446 reviews

Charming Victorian farmhouse 1880's bedrooms-2

Victorian farmhouse 1880's Stay in an "era gone by". Private 2 bedroom. Original hardwood floors. Original pocket doors. Sleeps 6. Has living room, kitchen, dinning area 1 bathroom with tub , study area. Charming town, population 4000+. smoke free house. Private keyless entry. The blue door. Free wifi, cable, roku. Has keurig coffee maker with free coffee, dishes, pots, pans, silverware, nu-wave cooktop, toaster, microwave, fridge, pack n play. Queen beds. W & D private.

Guest favorite

Rental unit in Freeport

4.92 out of 5 average rating, 214 reviews

1000 sq. ft. 1BR+ Apt Close to Town & Nature

This very spacious and light filled apartment has beautiful views of a marsh and the headwaters of the Harraseeket River. It is also across the street from a 100+ acre bird sanctuary. There is a queen bed in the bedroom, a twin in the large living room, and a twin in a small nook under the eaves off of the kitchen. You can put kayaks in across the street and it is a short 20 minute walk into downtown Freeport. Great year-round location.

Guest favorite

Guest suite in Bath

4.99 out of 5 average rating, 213 reviews

Bath Historic District Apartment

Located in the Bath historic district, this one bedroom apartment is located just a few blocks from downtown. The apartment has a queen bed in the bedroom and also a queen sleeper sofa in the living room. The home was built in the late 1700's, but with the recent upgrades, it now feels fresh with classic elements. Located in Midcoast Maine, this apartment is an quick drive to the beach, hiking trails and museums.

Guest favorite

Guest suite in Georgetown

4.97 out of 5 average rating, 349 reviews

Luxury suite, fireplace, jacuzzi

Private Suite in unique timberframe house. Great Room with 20' beamed ceilings, massive stone fireplace & terrace with 180-degree view. Kitchen & dining area. Marble bath with 2 person jacuzzi. Bedroom with queen bed & sitting area plus loft with 2 twin beds. The suite is totally private and separate from first floor owner of residence of owner. Water access for kayaking and canoeing.

Guest favorite

Guesthouse in Harpswell

4.95 out of 5 average rating, 453 reviews

Harpswell Studio on Waterview Property! Lobster!

Attached Cottage Style Studio! Clean, spacious, colorful, comfy, bright! New king bed! Easy access to Harpswell’s 216 miles of coastline via coastal trails, lovely side roads, small beaches and preserves. Too many trails to count in the surrounding area! Fresh lobster and seafood! Popham Beach and Reid State Park with expansive beaches are 35 minutes or less away.

Guest favorite

Rental unit in Brunswick

4.97 out of 5 average rating, 193 reviews

Garden view near Bowdoin College

Bedroom, full bathroom and laundry facility with private entrance. We are located in one of Brunswick’s most desirable neighborhoods: two blocks from the center of town, a 10 minute walk from Bowdoin campus. Historic downtown Brunswick. This is a perfect nightly rental for parents of Bowdoin athletes coming to catch the home game of their son or daughter.

Guest favorite

Home in Brunswick

4.93 out of 5 average rating, 242 reviews

A cozy, cute and comfortable house.

Cute and comfortable, 5 min. walk to restaurants, fast food, coffee shop, groceries and shopping centers. Also, bowling alley, miniature golf, driving range and cinema. Minutes by car to The Brunswick Executive Airport Downtown Brunswick Bowdoin College Maine State Music Theater Mid Coast Hospital Bailey Island Historic town of Bath

Guest favorite

Treehouse in Georgetown

4.97 out of 5 average rating, 326 reviews

Tree Dwelling with Water Views & Cedar Hot Tub (2)

Experience the airiness of life up among the pines in Georgetown, ME. Unique tree dwelling with cedar hot tub perched atop 21-acre wooded hill sloping to water views. Set in classic coastal Maine village w/ Reid State Park beaches and famed Five Islands Lobster Co. River views from the King size bed, through wall of windows.