Holiday houses 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, 132 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.

5.0 out of 5 average rating, 60 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

An evening view of the modern home displays a stone patio with a fire pit surrounded by seating. Soft lighting illuminates the pathway leading to the house, while trees create a natural backdrop. Access to the gazebo is visible in the background, enhancing the outdoor space.

4.96 out of 5 average rating, 57 reviews

Modern home on Southport Island

Modern 3 bed, 3 bath home sleeps 6 comfortably. Water views of Decker Cove from all bedrooms, easy walking distance to Robinson's Wharf & Restaurant. Luxury indoor/outdoor space with fire pit, gas grill, hard top gazebo, and 40 foot Farmers porch overlooking Decker Cove. Bring a boat and launch at the public launch 1/2 mile away! Central Air Conditioning, Radiant Heat, Gas Fireplace, Open Concept Living Dining and Kitchen with gas range, dishwasher, built in microwave and coffee station.

5.0 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.

4.86 out of 5 average rating, 22 reviews

A cozy bedroom features a queen bed dressed in white linens with a blue accent throw. Light-blue walls complement wooden beams overhead. A bedside lamp and stylish tray with decorative items are visible, alongside windows that allow natural light to fill the space.

Guesthouse in Southport

Ticket Office | Traveler’s Quaint Coastal Retreat

Situated in the heart of midcoast Maine, the “Ticket Office” is the perfect stay for a quick coastal stay. This tiny house provides a unique blend of modern comfort, new amenities, and New England charm. Local seafood restaurants and attractions are within a quick drive - or even walk - ensuring that you have a memorable stay. Spend time in the harbor experiencing the breathtaking beauty of a breezy coastal summer day. We invite you to relax and unwind at the “Ticket Office”.

5.0 out of 5 average rating, 205 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.

5.0 out of 5 average rating, 104 reviews

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.

Home in Boothbay Harbor

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!!

Apartment in Boothbay Harbor

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.

4.99 out of 5 average rating, 127 reviews

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.

Apartment in Boothbay Harbor

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.

5.0 out of 5 average rating, 141 reviews

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.

4.98 out of 5 average rating, 282 reviews

The exterior of a rustic mid-century cabin is framed by lush greenery, featuring a screened-in porch and wooden deck. Stairs lead up to the entrance, and natural stone accents create a seamless blend with the surrounding landscape.

Cabin in Boothbay Harbor

Lakeside 3 BR Cabin in Boothbay Harbor

This swanky mid-60's cabin sits on a hill overlooking West Harbor pond in the town of Boothbay Harbor. It offers privacy yet is close to everything downtown Boothbay Harbor has to offer. It is great for couples, solo adventurers, business travelers and families (with kids), and large enough to accommodate bigger groups. If you would like to bring along your canine pal feel free, they are welcome (sorry no cats).

Popular amenities for Southport holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Southport

The exterior of a historic two-story home is showcased, featuring a white façade and a black metal roof. Large windows allow for ample natural light, and a manicured lawn with small shrubs complements the entrance. A pathway leads to the welcoming front door.

4.88 out of 5 average rating, 43 reviews

Cozy Harbor Waterfront

4.86 out of 5 average rating, 63 reviews

Cottage in Southport

Little Nick by Sea Maine

An outdoor deck is furnished with a patterned tablecloth covering a dining table accompanied by six wooden chairs. Two lounge chairs are positioned nearby, offering views of the calm water, boats, and greenery. A flowering centerpiece adds a touch of color to the table.

5.0 out of 5 average rating, 29 reviews

Five Islands Waterfront Retreat

4.93 out of 5 average rating, 14 reviews

Bay View on Blueberry Hill

4.99 out of 5 average rating, 92 reviews

Home in Boothbay Harbor

The Happy Harbor House! Walk to town!

5.0 out of 5 average rating, 16 reviews

Home in Freeport

Mermaid's Chair | Private Beach | Hot Tub

4.95 out of 5 average rating, 55 reviews

A cozy living area is presented with a large arched window offering views of the outdoors. A small table is set for two, and colorful glass bottles are displayed above the window. Light hardwood floors complement the seating arrangement with plush chairs and a side table.

Home in Ocean Point

137 Shore Road Ocean Point view now with WiFi

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.