Holiday rentals in Southport

A comfortable outdoor seating area is arranged on a wooden deck, featuring a rectangular table surrounded by cushioned chairs. The space offers views of the surrounding trees and water, providing a serene setting for relaxation.

4.94 out of 5 average rating, 18 reviews

Southport, views of Christmas cove (Boothbay area)

Set on a hill above Christmas cove, enjoy water views from the deck or launch kayaks from the cove. Inside is a refreshed kitchen and full bath. Bedroom 1 has a Queen bed and half bath, bedroom 2 has a bunk and a twin bed and the loft has a king bed with half bath. Nearby are the Southport general store, Hendricks head beach, and Cozy’s dockside/Robinson’s wharf restaurants. Tour the Alpaca farm or drive to nearby Boothbay for a boat tour or the botanical gardens. Great for families and friends!

A three-story cottage is nestled on a hillside, showcasing large bay windows and a charming balcony adorned with decorative elements. Lush greenery surrounds the home, complementing its gentle color scheme against a clear blue sky.

4.92 out of 5 average rating, 106 reviews

Maine Cottage/Your Year-Round Destination

The Stowaway sits on 5.5 private acres atop a hill with breathtaking waterviews from every level. This pet-friendly, 3 story home offers 4 bedrooms, 3 baths & sleeps 8. Perfect for family getaways, milestone celebrations or relaxing escapes, the cottage combines comfort & style! The carriage house sleeps 4 more & together the property can host events of 50-150 guests (event fee $9000). Explore Maine's beauty year-round from summer by the sea, to colorful fall foliage, to snowy winter holidays.

The image captures an aerial view of a serene landscape with lush green trees surrounding calm waters. The shoreline curves gently, leading to a private dock that extends into the water. A soft sunset glow reflects off the surface, creating a peaceful ambiance.

4.99 out of 5 average rating, 130 reviews

Moss House: A Modern Waterfront Cabin in the Woods

Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

5 out of 5 average rating, 57 reviews

Cottage in Southport

THE COVE :New England Nautical charm

THE COVE : A charming romantic guest 2 story cottage. A Serene start : Peace, calm, tranquility. Hit the reset button & Gain a new perspective. Created with my own hands for Loved ones & wonderful Guest. Perfect for a couple or a friends getaway. Children always welcomed. Designed W/ New England Charm W/ splash of Nautical. Quality, Classic, simplicity at its finest. Tv / Internet one Provided in living room only as convenience only not integral to stay nor loss of power due to Mother Nature

5 out of 5 average rating, 17 reviews

Waterfront cottage with private dock Southport, ME

Enjoy an island getaway on a private island off Southport, ME yet only 10 minutes to Boothbay Harbor. The house sits on an acre of waterfront property with views of cozy harbor. House comes with a private dock (seasonal) and 2 kayaks. Master on first floor with King bed. Two additional bedrooms have a bunk and 2 twin beds. Enjoy a fully stocked kitchen so you can feel at home. Close to everything - Hendricks Head Beach, The Southport General store, restaurants, and Botanical Gardens.

5 out of 5 average rating, 202 reviews

Cabin in Georgetown

Near Beach+Cedar Sauna+Outdoor Shower+Pond+FirePit

Unwind at your own studio cabin with forest views, private sauna & pond! * New Private Cedar & Glass Barrel Sauna * Minutes to Reid State Park Beach & 5 Island🦞 * Fire Pit * Outdoor Shower * Rain Shower & Heated Bathroom Floor * AC/Heat * TV & Record Player w/Vinyl * Fast Wifi *Spruce Studio is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart & separated by a privacy screen and natural landscaping.

A modern kitchen is illuminated by a rustic light fixture with exposed bulbs, enhancing the open layout. Quartz countertops extend through the space, complemented by stainless steel appliances. A vase of mixed flowers sits on the counter, with a scenic view of the ocean visible through large windows.

5 out of 5 average rating, 104 reviews

Pinkham Cove - Water Front Cottage

Authentic oceanfront Maine home, with stunning views and amazing sunsets. Located on Pinkham Cove at the mouth of Boothbay Harbor. Experience the village of BBH , hiking trails, Botanical Gardens and explore the tranquility of Maine. This is the perfect getaway cottage. Enjoy the deck and beach access. The home was recently remodeled. The kitchen is a gem with quartz countertops and Bosch appliances. Curl up by the cozy fireplace, enjoy the amazing harbor view!!

4.98 out of 5 average rating, 40 reviews

A two-story cottage features grey siding and a covered front porch with seating. A white privacy fence encloses the yard, while natural rock formations and greenery highlight the landscape. Trees in the background provide a serene woodland setting.

Cottage in Southport

Classic Cottage on Southport Island

Decker Cove Year Round Cottage Our cottage is brand new, built in 2020, Radiant Heat on both 1st and 2nd floor. Enjoy the tranquility of a cozy cottage. King Select Comfort bed in master bedroom, 2nd floor bedroom has queen bed and sitting area, fold away dining table for four in the eat in kitchen, gas range with gas oven, microwave, Kuerig coffee maker, farmers porch on the front to enjoy the fall, winter and spring air. Enjoy coffee on the porch in any season.

4.99 out of 5 average rating, 123 reviews

An exterior view of the apartment's entrance is presented, featuring a small deck with two wooden chairs and a table. Colorful potted flowers line the steps leading up to the entrance, while a decorative red paddle hangs by the door, reflecting a nautical theme.

Flat in Boothbay Harbor

Chic 1-Bedroom at the Heart of Boothbay Harbor

Come and Stay in Oak Ledge! Oak Ledge is a beautifully-renovated 2-storey 1-bedroom apartment in the heart of Boothbay Harbor. Bedroom and Bathroom on the upper level. 2-night minimum 5-night maximum This is an adults only listing. Sorry, no pets. Our friendly rescue dog "Oscar" roams freely on the property. Off-street parking for one car. Self check-in. Smart TV with streaming - remember to have your log-ins.

5 out of 5 average rating, 139 reviews

A welcoming living space features two comfortable armchairs and a soft couch, with a wooden coffee table at the center. Large windows provide abundant natural light and views of the water. A well-equipped kitchen is visible in the background, along with light-colored cabinetry.

Flat in Boothbay Harbor

Sail Loft: Oceanfront Apartment on a Pier.

Experience a one-of-a-kind waterfront escape at the Sail Loft in Boothbay Harbor! This unique 1-bedroom apartment is located directly over the water in a working marina, offering stunning panoramic views from every window. It feels like being on a private yacht. Perfect for a couple's getaway, you're just a short walk from all the downtown shops and restaurants. Enjoy a truly memorable stay with free parking included.

Guest house in Boothbay Harbor

The cottage exterior features light-colored siding and a distinctive steeply pitched roof with a prominent window above the entrance. Double doors framed by a large glass panel invite visitors inside, surrounded by lush greenery and flowering shrubs.

5 out of 5 average rating, 268 reviews

The Sparrow’s Nest Charming Country Cottage

The Sparrow's Nest is located on a country road approximately 5 miles from downtown Boothbay Harbor. The Sheepscot River, it's coves and nature trails are close by. Enjoy the beautiful country surroundings, gardens, and the miracle of nature. What a delight to wake up to the sound of birdsong while enjoying a cup of local coffee, or sitting by the outdoor fire sipping wine and taking in the beautiful night sky.

The exterior of a two-story coastal house features a grey facade with white trim. Steps lead to a front door, while large windows offer views of the surrounding greenery. A deck with seating is visible to the right, inviting outdoor relaxation.

4.96 out of 5 average rating, 114 reviews

The Rowe House

Charming Coastal Cottage Walk to Harbor – Perfect Couples Escape w/ Private Setting The entire house is yours! 2 bedrooms, full bathroom, washer/dryer, a fully furnished living room, kitchen and dining room. Hardwood floors downstairs and carpet upstairs. Perfect for couples, solo adventurers, business travelers, small families and pets. NOTE: WE DO CHARGE $40 NON REFUNDABLE PET FEE PER PET DURING YOUR STAY.

Popular amenities for Southport holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Southport

5 out of 5 average rating, 90 reviews

The Happy Harbor House! Walk to town!

A tranquil scene captures a person walking along a wooden dock extending into calm waters. The surface reflects the warm hues of sunset, while trees frame the distant shoreline, creating a serene backdrop to the peaceful landscape.

4.91 out of 5 average rating, 22 reviews

Hall Bay Haven

4.94 out of 5 average rating, 90 reviews

Serene Coveside Cottage

A tranquil retreat is set amidst lush greenery, featuring a two-story structure with a sloped roof and large windows. A porch extends along the front, offering a spacious outdoor seating area. The surrounding landscape showcases tall trees gently framing the home along the water's edge.

4.86 out of 5 average rating, 22 reviews

Maine Coastal Retreat

4.85 out of 5 average rating, 60 reviews

Cottage in Southport

Little Nick by Sea Maine

A charming two-story cottage with a yellow exterior and a slate roof is surrounded by lush greenery. The inviting front porch features intricate white detailing. A gravel driveway leads to the entrance, while scenic views of the water are visible in the background.

4.97 out of 5 average rating, 32 reviews

Town’s End Cottage

A comfortable living area features a light gray sectional sofa adorned with decorative pillows. A simple white coffee table is centered in front of the couch, and a sleek television unit stands against the wall. Natural light enters through the windows, illuminating the space.

4.82 out of 5 average rating, 74 reviews

Lakeview House

The exterior of a modern house is depicted, featuring a unique architectural design with asymmetrical angles and a combination of white and dark elements. Surrounding trees provide a natural setting, and large windows reflect the surroundings, enhancing the house's connection to nature.