Family-friendly vacation rentals in Freeport

Waterfront Coastal Apartment | 5 Min to LLBean

Private waterfront guest apartment with king bed, pull-out sofa, kitchenette, walk-in shower, private entrances, and porch overlooking Harraseeket Cove for a relaxing coastal Maine getaway. Set on 8 private wooded acres with waterfront access to South Freeport Harbor, perfect for kayaking, wildlife, and enjoying nature. Peaceful and tucked away in the woods, yet only 5 minutes from LLBean, Freeport’s shops, restaurants, breweries, and bars. Wolfe’s Neck Woods State Park is less than a mile away.

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled in a private clearing in the woods. Explore island beaches and hidden trails. This yurt is “glampy” inside with leather chairs and a substantial log bed. The yurt has a rusticator kitchen with all of the basics for cooking: fridge, stovetop, sink, water, firepit & firewood. Outdoor shower. WiFi . Cozy heater for cool spring nights. Ferry options on Casco Bay Lines or CTC Ferry. Host provides transport to/from ferry to the yurt.

Charming Historic Freeport House

Bring the whole family to this historic house just minutes from downtown Freeport and the LL Bean flagship stores. The cozy central kitchen and dining are flanked by two separate living rooms making plenty of room for fun and relaxation! With two twin beds, toddler bed and full-sized crib we can accomodate any family. Catch glimpses of the Harraseeket River from this updated 1840s home on a half acre. A wonderful jumping off point for both Portland and the natural beauty of Mid-coast Maine!

The Outlet Studio, Rustic Comfort w Fireplace

Conveniently and perfectly located! Our studio is in a private building on a quiet dead end street yet walking distance to L.L. Bean, Bow Street Market, Leon Gorman Park, restaurants, breweries, live music, outlet shops, Freeport Farmers Market, the Amtrak station and all that downtown Freeport has to offer. A short drive to Wolfe's Neck State Park, Bradbury Mountain State Park, Mast Landing Audubon Sanctuary, the Desert of Maine, Winslow Park, farm stands and the beautiful mid-coast coast.

Crow’s Nest Tiny House at Old Crow Ranch

The Crow's Nest Tiny House sits nestled on Old Crow Ranch, a 70-acre working livestock farm, a true example of thriving Maine farmland. You'll be surrounded by fields and pine woods in Durham, Maine. Just outside Freeport and only 30 minutes from Portland, this cozy space makes a calming retreat away from the city - for a night or for a week. Fall asleep listening to the peepers and gazing at the stars, drink your morning coffee while looking out at the cattle grazing in the fields.

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

Cozy Maine Barn Hideaway- 2nd Floor Guesthouse

Welcome to our spacious 1000 sq. ft. Maine barn guesthouse! This bright and comfortable retreat is the perfect base for exploring all that Maine has to offer. Enjoy the fully-appointed kitchen, equipped with everything you need. The quiet bedrooms feature memory foam beds for a restful sleep, and the bathroom boasts a spacious shower. Please note that we have a no-pet policy due to allergies. Book your stay today and experience the best of Maine! Registration #: STRR-2021-24

Freeport Escape – LLBean | Fire Pit | 3 King | A/C

The Freeport Escape – A charming early 1900s home with modern amenities. Located in the heart of Freeport, walkable to shopping, restaurants, breweries, and the Amtrak station. Set on a private corner lot, enjoy the fire pit, porch grilling, and spacious outdoor area. Cozy up by the indoor fireplace in cooler months. Perfect for families, couples, and friends. 🛏️ 3 King Beds | Family-Friendly | ❄️ A/C | 🔥 Fire Pit | 🪵 Indoor Fireplace 📍 STRR-2022-82

Harraseeket Estuary Loft Apartment

Peaceful second-floor apartment in a charming barn building in Freeport, Maine. This private 1-bedroom space includes a cozy living room, full kitchen, and bathroom with shower stall. Surrounded by nature near the Harraseeket River, it’s the perfect relaxing getaway. Located just 10 minutes from downtown Freeport and about 1 mile from Wolfe’s Neck State Park, with easy access to hiking, shopping and dining.

Beautiful Home with Yard in Downtown Freeport

Beautifully appointed home, just a 5 min walk into town. Comfortable home in a quiet neighborhood, two queen bedrooms and two baths. A-C units throughout. Fully equipped kitchen: gas stove, dishwasher. Large living room with TV, wifi and work-space. Washer and dryer on-site. Whole house generator in case of power outage. Large backyard and private parking on-site. No shared spaces.

Studio Apartment in Freeport

Relax with your family in this modern studio apartment. Kids or adventurous adults will love climbing into the twin bed nook to read a book or sleep. Have a seat at the table to play a board game, eat a home cooked meal, or devour takeout. Lay in the king bed or sit on the couch to watch a movie or just relax. We are in a private wooded area just 5 minutes from downtown Freeport.

Gorgeous A-frame in a quiet campground - 15

The Escape is a gorgeous A-frame cabin that features a wall of 18' wall of glass overlooking beautiful woods. It is set among the tranquil northern pines of the recently renovated campground of the Desert of Maine. The cabin is 11/10 romantic and has everything you need to enjoy a luxurious, relaxing outdoor experience. Disconnect from the world at this beautiful A-frame!