Vacation rentals 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.

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.

Most Sought After Property on Lake Damariscotta!

Nestled on 3 acres with 450 feet of premier Lake Damariscotta frontage, this home has everything you could possibly dream of for the ideal family vacation, special occasion or company retreat. A perfectly spacious home for ALL seasons in Maine. Enjoy an exclusive dock, prime fishing, wine & smore's by the fire, snowmobiling trails, morning kayak excursions, tasteful ambiance thoughtfully put together by the owners of Row C and so much more! "Doing Something Common Uncommonly Well!" Cheers!

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.

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.

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!

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.

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 :-)

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.

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.

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.

Country View Cottage

Get away from the hustle and bustle in this secluded, solar-powered, off-grid cottage overlooking a pastoral farm meadow. Drive past the red barn with chickens and roosters often exploring, cow grazing near the pond,and enter your own private oasis. Enjoy your morning coffee watching the sunrise over the meadow from your screened porch, and possibly catch a glimpse of the wildlife that abound on this 87 acre coastal Maine farm.