Family-friendly vacation rentals in Waldoboro

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.

‘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.

River Escape - Studio Apt. with River Access

Large sunny basement studio apt. in private home with access to clean river! River down the hill 1/2 mile. 2 miles from town. Propane woodstove, lg. tile shower, deep claw-foot tub, soft water. new pillowtop queen bed. Open fields & path to river. Extra room with full fold out couch. Kid & pet friendly! Spectacular view from upper deck. Steps to bathroom and some to enter apt. Fresh flowers provided. Pick asparagus in spring! Warm cookies! Kayak nearby. Generator for storms. My artwork.

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.

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba

Waterfront Retreat with Gorgeous Views Stunning 3-bedroom, 2-bath home perfect for multi-generational gatherings. Features an open-concept layout, chef’s kitchen, 1st-floor bedroom and bath, 2nd floor with 2 bedrooms and 1 bath. Kayak from your backyard, hike nearby trails, or swim in Damariscotta Lake just a 5-minute walk away. Stay connected with high-speed fiber optic WiFi. Close to charming Newcastle and Damariscotta shops and restaurants. A true oasis for nature and relaxation lovers!

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.

Studio with Fireplace-Walkable to Downtown

Find peace at this private charming getaway perfect for a couple or a single guest. Stained glass and southern set windows add muted sunlight by day, while the warmth of a fireplace casts a glow by night. The bathroom is perfectly accommodating to the intimate space. A queen size Murphy bed creates comfort for slumber. While an inviting kitchen is equipped with amenities needed to make any chef sigh with relief. Whether for a few days or weeks, stop by to relax and restore.

Little Apple Cabin on 5 acres, amazing stargazing!

Little Apple Cabin is a private tiny cabin on five wooded acres, created for guests who want quiet, space, and deep rest. Surrounded by trees and farmland, it’s a simple, intentional place to slow down, sleep well, and enjoy Maine without crowds or noise. The cabin features a king bed on the main level, a cozy wood stove, and a wrap-around cedar deck for coffee, reading, and stargazing. Camden and Rockland are about 25 minutes away, and Belfast is about 30 minutes.

Private tree-top loft 5 minutes from Damariscotta.

Relax in this cozy loft with a light-filled deck overlooking the woods, but just five minutes to downtown Damariscotta. This brand new loft above our barn is cozy with all you need for a perfect vacation. You can relax with your morning coffee above the trees. It has an indoor toilet, sink and breakfast bar and outdoor shower. We’re a semi-retired couple and love to share our 62 acres property with stream and meadow. There are quite a few stairs to the loft.

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.

SNOW SWEET, A Yurt for All Seasons

Snow Sweet at The Appleton Retreat is very private, check out the Trail Map. This contemporary yurt faces the Field of Dreams and has a nice view of Appleton Ridge. It features a private therapeutic hot tub on the deck, a fire pit, and fast wifi. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.

Mystical Mary Howe Room, Downtown Damariscotta

This spacious studio apartment is perfect for relaxing after a day of exploring beautiful Damariscotta and surrounding communities. Situated on the third floor of one of Damariscotta's many historical buildings this apartment consists of a large living room area with kitchenette and a separate large bedroom with bath. Parking is right next to the building and a key will be provided for your apartment.