Waldoboro vacation rentals

4.92 out of 5 average rating, 119 reviews

A close-up view of blooming flowers and green leaves is captured in front of the entrance. The light-colored exterior of the historic Sea Merchant's house is visible through the open door, framed by traditional shutters.

Guest suite in Warren

Private Guest Suite in Midcoast Maine

Newly redecorated in 2024! A spacious, serene & private guest suite room with original details, private bathroom & king bed. In a historic Sea Merchant's house, this can be your home base as you explore the Midcoast & Penobscot Bay. Take a short drive to the surrounding coastal villages of Camden, Rockland, Damariscotta & more. Situated on a quiet road, 2 min. drive from Rt 90 (less traffic) & Rt 1, which will take you up & down the lovely coast of Maine. See our guidebook for recommendations!

Superhost

A welcoming living space is illuminated by outdoor string lights, with large windows framing picturesque views of a lake at sunset. A cozy fire pit is visible outside, with smoke rising softly into the evening sky, creating a peaceful ambiance.

Farm stay in Union

4.91 out of 5 average rating, 161 reviews

Newly renovated home on historical Waterfront farm

28 acre property is a Forever Farm surrounded by rolling hills and Lake frontage . This farm is also referenced in the historical book “ Come Spring “ we purchased this beautiful property in 2019 and have spent the last year renovating it. Our favorite part of the home are the floor to ceiling windows overlooking the round Pond . This is very peaceful retreat. On a daily basis , you can pick your own fresh eggs from coop and feed our pigs . We are 15min to Camden ,Rockport , Rockland .

4.92 out of 5 average rating, 183 reviews

An exterior view displays a newly constructed set of wooden stairs leading to a deck above. The stairs are framed with pale wooden railings and are flanked by a red building. The sky is bright with scattered clouds.

Apartment in Nobleboro

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.

4.98 out of 5 average rating, 439 reviews

A colorful garden area features a variety of flowering plants in vibrant hues. A stone wall borders the garden, while flowering window boxes add charm to the exterior of the house. Bright green foliage complements the floral display under clear blue skies.

Guest suite in Rockland

5 Laurel Studio private entrance STR20-69

Open concept small studio, private patio and entrance, full kitchen. *SHARED wall between studio and main house, therefore some shared noise. 2 minute walk to the ocean , Lobster and Blues Festivals. A small swimming beach is a 5 minute walK, 5-10 minutes to the Farnsworth and CMCA museums, Strand Theater, restaurants, antiques shops & galleries. ALSO NOTE we do not have television. We have wifi but you must bring your own device . EXEMPT FROM ACCEPTING SERVICE DOG

Cottage in South Thomaston

An aerial view reveals an open-concept living space featuring warm wood accents and large windows. A cozy seating area with neutral-colored sofas is paired with a wooden dining table. Natural light floods the room, highlighting the modern kitchen appliances and inviting atmosphere.

4.95 out of 5 average rating, 169 reviews

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.

4.85 out of 5 average rating, 517 reviews

"Ship Shape": waterfront, cozy studio- downtown

Located in a historic 200 year old building "Ship Shape" is close to downtown but on a quiet tree-lined residential street. It is just one block to the library, bookstore, post office and all the lovely shops. It is on the shore of the Damariscotta River with wonderful views from inside and out.. You’ll love my place because of the neighborhood, the light, the outdoor space, and the comfortable bed. My place is good for couples and solo adventurers.

4.98 out of 5 average rating, 106 reviews

An open-concept kitchen and living area features a wooden ceiling with exposed beams. A sleek kitchen island with seating is illuminated by pendant lighting. Light reflects off stainless steel appliances, while a vibrant orange door frames the view of the surrounding greenery.

Guesthouse in Newcastle

Modern 1-BR I Wooded Retreat I Mid-Coast Maine

Escape to your perfect Midcoast Maine base camp—just 5 min to Damariscotta/Newcastle & 1 hr 6 min to PWM. Enjoy forest views, modern comforts, and easy access to the coast. • King bed + ensuite • Fully equipped kitchen + charcoal BBQ • Vaulted ceilings, wall of windows, open layout • Private deck, fire pit • WiFi, laundry, parking • Generator (2024) for year-round comfort Ideal for foodies, outdoor lovers & oyster fans!

A three-story historical building with white siding features multiple dormer windows and a welcoming entrance adorned with flowers. Lush greenery surrounds the structure, completing a charming exterior that reflects the character of Damariscotta.

4.92 out of 5 average rating, 203 reviews

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.

The living area features bright yellow walls and ample natural light from multiple windows. A round table with floral tablecloth sits center stage, surrounded by chairs. Two couches, one textured and the other a neutral tone, are positioned near the walls adorned with artwork.

4.92 out of 5 average rating, 286 reviews

Fernald's Backside

Fernald's Backside is a sunny, comfortable 2nd floor apartment , tucked behind S. Fernald's Country Store in the heart of downtown Damariscotta. It features a deck with views of the Damariscotta River and Harbor. A one bedroom apartment with ample living space and full kitchen, it can sleep 5 with a double and single bed and a sleeper sofa. Fernald's Backside is Pet free.

4.92 out of 5 average rating, 110 reviews

The exterior of the cottage showcases a charming A-frame structure, bordered by vibrant gardens filled with various flowers. A wooden balcony extends from the upper level, offering an elevated view of the surrounding landscape and greenery under a soft sunset sky.

Cottage in Union

Cozy Lakeside Getaway | Seven Tree Cottage

This newly renovated, cozy getaway is an ideal escape for a couple, small family or friends. Less than 20 minutes from the charming oceanside towns of Rockland and Camden, the cottage is named after Seven Tree Pond, offering guests waterfront views in the winter, with lake access (boat launch, picnic area, and swimming access) less than a 5 minute drive.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Waldoboro vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Waldoboro

4.98 out of 5 average rating, 63 reviews

A decorative dragonfly sculpture is mounted on the underside of a wooden porch beam, with string lights hanging nearby. The background features a lush green landscape leading into blueberry fields, complemented by distant trees under a clear sky.

Apartment in Washington

The Adams Suite on U-pick Blueberry Farm

Superhost

An aerial view reveals a lush landscape surrounding a coastline, with abundant trees and greenery punctuating the property. The shoreline features a mix of sandy and rocky areas gently meeting the water, providing a serene and natural setting for relaxation and exploration.

Guesthouse in St. George

4.91 out of 5 average rating, 57 reviews

Timber frame studio on the ocean

4.97 out of 5 average rating, 64 reviews

Two chickens are spotted in a grassy field during sunset. A rooster stands proudly beside a hen, with a greenhouse and trees in the background, showcasing the natural beauty of the farm's landscape.

Guesthouse in Jefferson

Oasis Family Farm Near Hidden Valley

A modern bathroom features a glass-enclosed shower with a sleek stone bench and intricate tile work. Natural light filters through a window adorned with a small plant. Soft towels hang neatly beside the shower, and a textured rug lies on the floor.

4.91 out of 5 average rating, 23 reviews

Damariscotta River Downtown Loft

4.98 out of 5 average rating, 45 reviews

A wooden dock extends into a calm lake, surrounded by lush greenery. Reflections of trees and clouds can be seen on the water's surface, enhancing the serene atmosphere of the area.

Apartment in Hope

Highfields Dahlia Farm

4.97 out of 5 average rating, 95 reviews

Guesthouse in Cushing

Look! River Run Cottage on tidal salt waterfront

4.98 out of 5 average rating, 61 reviews

A large eagle is perched on its nest nestled high in a tree, surrounded by vibrant green foliage. The tree's branches provide a natural frame, with soft spring leaves in various shades of green creating a peaceful scene.

Home in Cushing

River Watch Cottage