Holiday houses in Waldoboro

Steps to Water | Wood-Burning Sauna Maine Retreat

An Airbnb Guest Favorite, Spruce Ledge sleeps 12 on the Midcoast Maine waterfront. Steps to the water, private wood-burning sauna, tennis & pickleball, paddleboards, Peloton, firepit, and a fully equipped kitchen with upper and lower dining patios. Cold plunge in the spring-fed pond or swim off the dock in the ocean. Our lobsterman neighbor sells fresh catch right off the dock. Camden, Rockport, Damariscotta & Boothbay all within 20 min. EV charging on-site. Built for groups. Made for memories.

Location · Family · Indoor spaces

Renovated 1911 Farmhouse on Peaceful Peninsula

Fair View Farm is a 1911 boardinghouse that was lovingly renovated In 2021 with an eye toward keeping original details. The house is bright and open with a large yard, 5 acres of woods leading to a salt water tidal river that leads to Muscongus Bay. The street is a quiet neighborhood on a peninsula with within a mile of 2 public preserves with hiking trails, and a short drive to town. The house comes with a fully equipped kitchen, TV with surround sound, puzzles, games and books for your use.

Family · Location · Barbecue

The Midcoast Mainstay

Historic 1910 Colonial home in the heart of Waldoboro. Close to trails and kayak launches on the Medomak River leading to Muscongus Bay. Located between Portland and Acadia for easy access to all of the Midcoast. Enjoy local dining, arts, and theater in walking distance. The home includes a full kitchen, high ceilings, 3 bedrooms, 1.5 bathrooms, a play room, sun porch, free parking, culinary and floral gardens, WiFi, Roku, books, games, and a studio for yoga, work, meditation, or relaxing.

Family · Value · Comfort

The Cottage on North Pond.

Escape to the tranquility of lakeside living with this beautifully maintained 3-bedroom, 2-bath home nestled on the shores of North Pond, one of Maine’s pristine bodies of water. Whether you're seeking a peaceful retreat or basecamp to explore the midcoast region, this property offers the perfect blend of comfort, natural beauty, and classic Maine charm. Enjoy your mornings on the deck with coffee in hand, listening to the loons call across the water, or watch the eagles fish in the cove.

Family · Value · Nearby

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!

Location · Value · Air conditioning

Long View Cottage on Pristine Broad Bay

Recent renovated 1,500 sq. ft. light-filled mid-century cottage on a beautiful peninsula overlooking Broad Bay. Eight acres of open fields down to one of the most pristine saltwater bays in Maine. Two private suites, each with their own access to the large open cedar deck with plenty of seating for sun bathing in the morning and cocktails in the evening. An outdoor shower for those who hate to come indoors. A fully equipped cook's kitchen. Washer and dryer. Three zones of air conditioning.

Value · Location · Check-in

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.

Value · Family · Parks

Farmstay private entrance

Relax at this peaceful place to stay. There is no kitchen, but there is a small fridge, a microwave, and a coffee maker. If you are a spinner, or want to learn, please join us for Fiber Sunday 1 - 3 each week this summer. Enjoy the charisma of this old farm. It is a quiet place to to come after a sightseeing day, with a private porch. The bedrooms are located upstairs. Our living space is downstairs. There are 70 acres of fields and woods here with walking and riding trails.

Location · Family · Comfort

Cozy Private Waterfront Camp

Discover our charming family cabin, located on the water, for your perfect Midcoast Maine getaway. An ideal retreat from the hustle and bustle of everyday life. Enjoy breathtaking views and sunsets, cozy lodging, private water access and docks, an attached sunroom, and kayaks, paddle boat/board, and more. Located in Waldoboro is a small town in the heart of Maine with all the cities on your bucket list nearby - Rockland, Camden, Damariscotta, Pemaquid, and Boothbay Harbor.

Location · Value · Nearby

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!

Location · Family · Bathroom

Applecroft Cabin No. 1

Simple and clean, our modern structure is just a small porch and single open room with a huge glass sliding door. Inside is a brand new queen size bed with linen sheets, down pillows and a thick down comforter. You park and hike into the cabin and will have total privacy and peace here. The cabin has a large fire pit with chairs and a table and a grill for you to cook over the fire. There is an outhouse nearby and a huge pond to swim in.

Location · Hospitality · Check-in

Lakefront Home

This year-round home can be anything you want it to be. It’s a place to create memories, recharge and relax. Enjoy the stone fire pit on the point with a view down the lake. Take walks on the private dirt roads, walk or cross-country ski on the frozen lake. This rental offers views of the lake from three sides of the house with it’s many windows and large sliders. This is a place you will not want to leave.

Family · Location · Access