Family-friendly vacation rentals in Waldoboro

‘Round the Bend Farm - private, modern cabin

Our newly built, modern cabin offers a secluded and relaxing retreat in Union, Maine. With the high ceilings, open floor plan, and many windows, guests are surrounded by natural light and forest views. The cabin has a fully equipped kitchen, a cozy fireplace, and an outdoor grill and fire pit. Walking trails connect the cabin to our farm next door, where you can visit with our horses, donkeys, goats, chickens, and ducks. We are just 25 minutes from the Midcoast's shops, restaurants, and beaches.

Country home ~ Family friendly

Our converted barn is located on a little used road with easy access to miles of trails. Our road is little used but intersects with US 1.There is a downstairs bedroom with an open loft on the second floor. Wonderful light and views. A fire-pit, swings, hammocks, and playground structures make this a perfect place to stay with your family. A peaceful place to visit for all ages. World famous Moody's diner, a grocery store and gas stations etc. are just 3 miles away! Perfect for young children.

The Apple Blossom Cottage

The Apple Blossom is located in the heart of historic Union village,in Sky Orchard. It is nestled down the hill in a private orchard.The tiniest of tiny houses.Two minutes to pizza,The Sterlingtown Public House,coffee shop,and grocery.15 minutes from the ocean!Sit on the deck and watch the fireflies in the field.With a fireplace and view of the blueberry hills.Curl up, listen to the rain on the tin roof,awaken to the sunrise through the antique lace curtains.This place will fill your soul.

The Washington Suite on u-pick blueberry farm.

This unique place has a style all its own. No, he didn’t sleep here, Washington that is, but now you can. Our one-hundred-acre farm is located in the small rural village of Washington. It is located just 2/10 of a mile from the village center where the general store, library and town offices are located. Easy commute east to the coast and the must-see towns of Rockland, Rockport and Camden or west to our capitol, Augusta. One hour and forty minutes to Bar Harbor and Acadia national park.

Finding Joy

This lovely apartment is above our garage. You can come and go as you please. We have created a place for peace and solitude. Sit on the deck or look out the dining room window and see the woods and wait for the birds and wildlife that may be wonder through the yard. There is coffee and tea available, along with basic breakfast supplies, if you wish. Keyless entry allows for you to come anytime after check-in. Please note, you have to be comfortable with stairs to access the apartment.

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 Copper Fox Treehouse

Named the 10th most spectacular tree house in the world by the BBC Featured in the book: Modern Tree Houses by Taschen Airbnb's Most wishlisted property in Maine in 2025! Come experience the whimsy and craftsmanship of this red fox head shaped treehouse for yourself. The magic of this wild adventure awaits you in the treetops... Come to relax, explore and make lasting memories your family and friends will talk about for years. Follow our journey on IG at @thecopperfoxtreehouse

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

1830s Cape hosted by George & Paul

This 1830 cape is for rent by the month or weekly or for a two-night minimum stay. It is located at the edge of the historic village of Waldoboro. It offers a convenient base to sightseeing in midcoast Maine. It’s old-fashioned, decorated with plants, antiques and paintings and features a large, fully equipped kitchen, music room with piano, television room with pull-out sofa, full bath with stall shower and outside patio. Your hosts are right across the driveway.

Timeless Tides Cottage

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.

Retreat at Sea Cloud Cottage in Historic Wiscasset

Welcome to Sea Cloud Cottage - A Charming Retreat in Wiscasset, Maine Sea Cloud Cottage is a beautiful one-bedroom home, once the guest house to the larger Acorn Cottage next door. Perfectly designed for a couple or small family (with an extra child or adult on the pull-out sofa), this 900-square-foot gem offers an inviting, comfortable space for your getaway. You can also rent it alongside Acorn Cottage for larger parties, accommodating up to 9 guests.

Cozy Carriage House in Downtown Damariscotta

Welcome to Damariscotta, Maine! Our carriage house apartment has the rustic, romantic feel of a classic Maine cabin, but is located a short walk from downtown Damariscotta. Guests have a private studio that includes sleeping accommodations, a bathroom, a small kitchen area, and closet space. This is the perfect spot for adventurous travelers who want to explore the Midcoast of Maine like a local or for creative folks to unplug and focus on their craft.