Vacation rentals in Waldoboro

4.99 out of 5 average rating, 163 reviews

A serene waterfront view captures calm waters reflecting the sky and surrounding landscape. Lush greenery is visible along the shore, while scattered clouds drift across the blue sky. The tranquil scene invites relaxation and appreciation of nature.

Home in Newcastle

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!

4.92 out of 5 average rating, 187 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, 46 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, 124 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!

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, 216 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.

Apartment in Damariscotta

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.

4.85 out of 5 average rating, 525 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.

4.83 out of 5 average rating, 226 reviews

A geodesic dome is nestled in a field, surrounded by lush greenery, under a vibrant sunset sky. The structure features large, hexagonal windows that reflect the warm colors of the sunset while offering a serene and tranquil ambiance.

Dome in Union

Dome 4 at Come Spring Farm

Our geodesic domes sit in on 10 acres of our property . In total come spring farm is 28 acres , you will have access to round pond to kayak , fish or swim. You may also visit the Alpacas , bunnies , pigs , sheep and our new lounge area opening June . The bathroom facilities are private for each dome, no sharing .You will need to walk to bathhouse . Pocket WiFi can be provided if requested . Follow us on IG at Comespringfarm .

4.98 out of 5 average rating, 107 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!

Apartment in Damariscotta

A cozy corner of the studio apartment features a tan armchair with decorative stitching. A small dining table is set nearby, and the kitchenette is visible in the background, equipped with wooden cabinets, plates, and essential appliances.

4.92 out of 5 average rating, 209 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.

4.92 out of 5 average rating, 113 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.

4.97 out of 5 average rating, 36 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

4.98 out of 5 average rating, 65 reviews

The exterior of a vibrant orange building is shown, featuring a covered porch with a welcome sign. Lush greenery and flowering plants surround the entrance, while a pebbled pathway leads to the door, creating an inviting approach to the accommodation.

Apartment in Washington

The Adams Suite on U-pick Blueberry Farm

A rustic cabin is nestled among vibrant trees along the shoreline of a calm lake. A wooden dock extends into the water, providing access. The natural surroundings create a serene atmosphere, with greenery reflecting on the lake's surface.

Cabin in Jefferson

4.87 out of 5 average rating, 122 reviews

Loon Lodge

5 out of 5 average rating, 3 reviews

A cozy sleeping area is visible through a wooden doorway, showcasing a bed with a plaid blanket. Soft linens are neatly arranged, with a bedside lamp providing warm light. The rustic wooden walls and ceiling add to the cabin's charm, with a small window allowing natural light to enter.

Cabin in Bremen

Sauna + Stay in MidCoast Maine - Cabin 3

4.91 out of 5 average rating, 58 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

4.97 out of 5 average rating, 37 reviews

A spacious living room features two turquoise sofas, accented by an area rug with a geometric pattern. Natural light flows through the large windows, and a fireplace is positioned against the far wall. Wooden panels add warmth to the overall design.

Home in Friendship

Captain's Quarters

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.

Home in Waldoboro

4.84 out of 5 average rating, 191 reviews

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

4.84 out of 5 average rating, 87 reviews

The farmhouse is depicted with a classic wooden exterior, featuring a combination of light-colored shingles and a red accent. Large windows allow natural light to fill the interior. A screened porch is visible, providing a shaded area for relaxation.

Home in Warren

Book now & visit the beautiful mid-coast area!