House holiday rentals in Damariscotta

Peaceful & Cozy, A Maine Retreat

Escape to the beautiful Maine coast. Let your eyes relax in the deep green beauty of the timbers that surround this serene lake region. Our cozy, A-frame chalet minutes from Damariscotta is a rare gem that will have you coming back year after year. Take advantage of the private waterfront and swim in the pristine waters of McCurdy Pond. Eat a lobster dinner outside on the wrap-around deck or gather around the firepit and enjoy the fresh Maine coastal air. This home has relaxation in spades!

Family · Location · Comfort

Loon’s Cry Lakefront Cottage

This charming cottage is located on pristine Lake Pemaquid and sits 35' feet from the water's edge with a sandy beach and dock area. The cottage is newly renovated with a bright and airy open floor plan, granite countertops, a wall of windows, wood floors, fully stocked kitchen, clean & comfortable beds, quality linens, fast internet, RokuTV and an open floor plan that is inviting with picturesque views. Attention to detail in this luxe stay that is meticulously maintained & close to everything.

Location · Family · Hospitality

Moss House: A Modern Waterfront Cabin in the Woods

Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

Family · Location · Kitchen

Kens Cottage in Round Pond ME

Take it easy at this unique and tranquil getaway. Round Pond is a very special village in Muscongus Bay. It is comprised of a large natural cove filled with an array of boats from working lobster boats to gorgeous pleasure crafts. Located on the Northern Point of Round Pond Harbor the views on the property are stunning. You could be taking in the activity of the harbor in one direction, then watch sailing classes and lobster boats working off Loud's Island in another or just gaze down the bay.

Value · Location · Walkability

Coastal 4BR Farmhouse w/ Water Views, Walk to Town

THE EVERGREEN HOUSE 🌲 Escape to our charming coastal farmhouse in the heart of Newcastle, ME, the perfect home base for exploring the best of Midcoast. Just a short walk to the Twin Villages of Damariscotta & Newcastle, you'll be immersed in a vibrant local scene with incredible restaurants, bars, shopping, & oysters at every turn. A few miles from renowned oyster farms, a winery, brewery, and distillery, and Maine's rocky coastline. Venture up & down the coast and take in the best of Maine!

Location · Family · Outdoor spaces

Hermit Thrush House

The 1 bedroom, 1 and 1/2 bathroom with laundry apartment is located at: 19 POORHOUSE COVE ROAD in South Bristol, Maine 04568. The apartment has skylights in the living room and kitchen and is located on a private property as a stand alone guest house. Close to Christmas Cove, Wawenock public/private golf course and 15 miles from scenic Damariscotta and the Pemaquid peninsula with a public white sand beach. Our waterfront is Poorhouse Cove, an estuary off of the Gulf of Maine, Atlantic Ocean.

Location · Family · View

Summer on Biscay Lake: Private Dock, Water Access

Welcome to your Maine summer escape on Biscay Lake. This lakefront cottage sits steps from the water, with a private dock for swimming, kayaking, or simply drifting through the day. Mornings begin on the deck with coffee, afternoons unfold on the lake, and evenings gather around the fire pit as the sun sets. The atmosphere is easy & relaxed; a place to unwind, and enjoy the simple rhythm of summer. Conveniently located near coastal towns & outdoor destinations, while feeling tucked away.

Family · Location · Outdoor spaces

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!

Value · Family · Accuracy

Maine Waterfront Hideaway

You won't find mobs of tourists here but you will experience a working lobstering village in Maine. Sit back, relax and enjoy the quiet and privacy of 2+ acres at the end of a dirt road with a huge dock located on a tidal cove. Great for family reunions with lots of space and activities for folks of all ages. We focus on making the house comfortable and don't want you to worry about the little things like feet on the couch, water rings on the table or a broken glass. Life happens :-)

Value · Family · Long stay

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.

Family · Value · Laundry

Peaceful Maine Haven

Rest and relax in this cozy cottage by the sea. Home has new appliances, kitchen, bathroom, flooring, furniture, doors, and paint! Located towards the end of one of Maine's peninsulas, this property is on a quiet road that is perfect for taking a walk or running with lots of sights to see! There is a marsh on one side of the home with birds and wildlife year-round; fox, deer, frogs, turkeys to name a few. Plenty of adventure awaits or cozy up and rest!

Family · Location · Bathroom

Coastal Maine Retreat · Fire Pit · Walk to Harbor

Tucked into the woods of Round Pond, one of Maine's most beloved working harbor villages, The Round Pond Getaway at Moxie Cove is your base for the best of Midcoast Maine. Walk five minutes to the water, spend evenings around the fire pit, and wake up to nothing but birdsong on the screened porch. Pemaquid Lighthouse, fresh lobster at Muscongus Bay, and the Coastal Maine Botanical Gardens are all within easy reach.

Location · Family · Layout