Vacation rentals in Waldoboro

4.92 out of 5 average rating, 189 reviews

A charming red house is visible from the winding driveway, framed by tall trees and patchy grass. The front porch runs along the house, while two garage doors and a wooden structure are located nearby. A dog can be seen walking along the pathway.

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, 49 reviews

The cottage exterior is characterized by a white wood facade and a gently sloped roof. A set of stairs leads to a screened porch with large windows. Surrounding greenery includes trees and a well-maintained lawn with decorative stones.

Cabin in Waldoboro

Country View Cottage

Get away from the hustle and bustle in this newly built, secluded, solar-powered, off-grid cottage overlooking a pastoral farm meadow. Drive past the red barn with chickens free-ranging, cattle grazing, 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 deer and other wildlife that abound on this 81 acre family farm 5 miles north of Route 1 and famous Moody's Diner.

4.91 out of 5 average rating, 128 reviews

A spacious guest room features a king bed with a soft quilt and several plush pillows. Original details are highlighted by a decorative fireplace surrounded by tile. Natural light fills the room, complemented by light-colored walls and elegant wall sconces.

Guest suite in Warren

Private Guest Suite in Midcoast Maine

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!

Guesthouse in Damariscotta

A cozy wooden structure with a unique triangular roof is surrounded by a lush garden. Raised planting beds filled with greenery and blooming flowers are visible in the foreground, complemented by a pathway that leads up to the house's glass doors.

4.95 out of 5 average rating, 100 reviews

Private tree-top loft 5 minutes from Damariscotta.

Relax in this cozy loft with a light-filled deck overlooking the woods, but just five minutes to downtown Damariscotta. This brand new loft above our barn is cozy with all you need for a perfect vacation. You can relax with your morning coffee above the trees. It has an indoor toilet, sink and breakfast bar and outdoor shower. We’re a semi-retired couple and love to share our 62 acres property with stream and meadow. There are quite a few stairs to the loft.

The exterior of a charming yellow house is presented, featuring white stairs leading to a green front door with an ornamental design. Lush shrubs frame the entrance, and tall trees provide shade to the vicinity, creating a welcoming appearance.

4.99 out of 5 average rating, 94 reviews

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.

Superhost

The kitchen features a combination of white cabinetry and a wooden countertop. High-end appliances, including a stove and microwave, are visible. Shelving holds various dishes and kitchenware. Natural light enters through a window, illuminating the space and enhancing its functionality.

4.83 out of 5 average rating, 30 reviews

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!

Guest suite in Damariscotta

A spacious studio apartment features wooden paneling and warm lighting. A queen bed with white linens is flanked by two bedside tables with lamps. A small breakfast nook with a checked tablecloth is visible, along with a desk and wooden chair.

4.94 out of 5 average rating, 220 reviews

Cozy Carriage House in Downtown Damariscotta

Welcome to Damariscotta, Maine! Our carriage house apartment has the rustic, romantic feel of a classic Maine cabin, but is located a short walk from downtown Damariscotta. Guests have a private studio that includes sleeping accommodations, a bathroom, a small kitchen area, and closet space. This is the perfect spot for adventurous travelers who want to explore the Midcoast of Maine like a local or for creative folks to unplug and focus on their craft.

Superhost

A cozy bedroom features a wooden bed with a patterned quilt and two decorative pillows. Natural light streams in through large windows with floral curtains. A wooden rocking chair and a small table are positioned nearby, creating a inviting space to relax.

Apartment in Damariscotta

4.84 out of 5 average rating, 534 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, 110 reviews

The modern retreat is nestled among trees, featuring a deck with outdoor seating and a picnic table. The structure showcases large windows, allowing natural light to fill the interior, with a welcoming red door standing out against the dark exterior.

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!

4.92 out of 5 average rating, 115 reviews

A charming cottage is showcased with a blue front door and an inviting facade. Lush greenery surrounds the stone pathway leading to the entrance, with gardens visible to the sides. A balcony is seen above, framed by trees against 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.

4.98 out of 5 average rating, 40 reviews

A colorful sunset is captured, displaying shades of pink and orange in the sky. Dark silhouettes of trees frame the image, with a hint of water visible in the foreground. The tranquil scene reflects the natural beauty of the surroundings.

Farm stay in Waldoboro

Island View Farm

When you are thinking of getting away or just need a rest, come and go glamping on our mini-farm. We would love to share our beautiful view and outstanding sunsets. Nighttime offers amazing stars (when cloudless) and sounds of the country. This family setting is perfect to settle in for a week or two.

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Popular amenities for Waldoboro vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Waldoboro

4.92 out of 5 average rating, 60 reviews

An open living area features exposed timber beams and a large green sofa with decorative pillows. In the background, a spacious bed is visible through an arched window. A round dining table with chairs is located to the right, and natural light fills the space.

Guesthouse in St. George

Timber frame studio on the ocean

5 out of 5 average rating, 9 reviews

A spacious house is set on a well-manicured lawn, surrounded by trees. The building features a wide porch with two turquoise chairs facing a garden, while large windows illuminate the interior. A gentle slope leads to the surrounding greenery, creating a peaceful environment.

Apartment in Waldoboro

Farmstay private entrance

Superhost

The cottage exterior is shown with a light yellow facade and a gray roof. A spacious deck with white chairs and a dark blanket is visible, surrounded by green grass and trees. A large tree stump sits in the foreground.

Cottage in Jefferson

4.86 out of 5 average rating, 42 reviews

Gorgeous Lake House Right on the Water!

A spacious kitchen featuring a central red island with a wooden countertop and an array of cooking pots hanging overhead. Rustic wooden beams and walls complement the stainless-steel appliances, while decorative items and artwork add charm to the warm atmosphere.

4.84 out of 5 average rating, 191 reviews

Thistledown Farm's Pennysworth - An 1800's barn.

Place to stay in Waldoboro

A spacious bed is adorned with patterned bedding and multiple decorative pillows. The wooden headboard features intricate carvings. A small bedside table is positioned next to the bed. Elegant wallpaper adds a touch of color to the room's ambiance.

4.91 out of 5 average rating, 54 reviews

Cookhouse Loft. A suite of rustic accommodations.

A spacious living area features large glass windows that provide sweeping views of the river. Plentiful natural light illuminates the room, which includes a comfortable sofa and a patterned accent chair. A modern glass coffee table sits atop a textured area rug, enhancing the inviting atmosphere.

4.84 out of 5 average rating, 32 reviews

Remodeled 2BR Riverfront | Dock

5 out of 5 average rating, 7 reviews

A wooden dock extends over calm waters, leading to a floating platform. Lush greenery frames the scene, with tall trees providing shade. A colorful inflatable toy rests on the grassy shore, adding a playful touch to the serene lakeside setting.

Cottage in Waldoboro

Cottage Waterfront Retreat

A bright kitchen space reveals a round, wooden dining table surrounded by six white chairs. Cabinets line one wall, complemented by modern appliances, including a stove and dishwasher. Natural light pours in through two large windows, highlighting the patterned area rug beneath the table.