Vacation rentals in Waldoboro

Lake House on Pulpit Rock

Perched atop “Pulpit Rock” on Lake Damariscotta, this modern lake retreat offers stunning panoramic views and total Maine woods serenity. Listen to loons, watch bald eagles, and enjoy swimming, canoeing, or kayaking right from the private dock. This cozy home features an upstairs bedroom, workspace with fast WiFi (100MB), and half bath. Downstairs includes a full bath, open kitchen/living area, and sleeper sofa. Outside, enjoy a picnic table, chairs, and grill for lakeside meals and relaxation.

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.

Cabot Lodge Waldoboro/Townhouse with Private Spa

This stylish apartment is perfect for one person or up to two couples and a couple singles; two queen bed suites/a large shared bath. Additionally, theres a trundle bed that sleeps two in the library with powderoom. Sophisticated with a spacious waterview deck, private bar/dance floor. Cozy with a fireplace, library. Restorative with a jacuzzi tub and sauna. We offer a list of vetted massage therapists for in room treatments.Centrally located and walkable. #perchcafe #waldotheatre #narrows

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.

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.

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 free-ranging, serene 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. ***NOTE. We are unsure we will have cattle this summer due to lack of availability.

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.

Timeless Tides Cottage

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own private 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.

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.