Holiday houses in Southport

Rosie's Hideaway By the Sea

Rosie's Hideaway By The Sea is in a lovely turn of the century Victorian farm house filled with paintings by Maine artists and beautiful hardwood floors. The front yard has gorgeous shade trees and a stone wall. Fabulous views of the harbor is a short walk away. . Follow the road along the harbor and you'll end up downtown Boothbay Harbor where all the shops and restaurants are. While we love children and animals, the space is not appropriate / safe for children under 8 or pets of any kind.

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!

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.

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.

Cozy Harbor Waterfront

This historic home was once the lightkeeper’s house and has been beautifully renovated with four bedrooms and three bathrooms. Located on idyllic Southport Island, the home feels peaceful and tucked away while still being easily accessible by a swing bridge, so you are never truly isolated. It is a short walk down to Cozy’s Dockside Restaurant where you have a perfect view of all the boats in the harbor. It’s a 10-minute walk to the Southport General Store which has great coffee and food.

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.

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!!

Perched atop the Coast of the Atlantic Ocean

Enjoy sweeping vistas of the Atlantic Ocean from this 2002 home perched among spruce trees above the rocky coast. Watch for bald eagles and seals. Fall asleep to the sound of crashing waves. Walk down to the edge of the ocean to lounge or picnic. Walk 6 minutes or drive the 0.1 miles to the park entrance. Hike the Little River Trail. The house has vaulted ceilings, panoramic views, fully equipped kitchen, and whirlpool bath.

Architectural gem near Botanical Gardens

Just 12 minutes from Coastal Maine Botanical Gardens, home to Gardens Aglow. Welcome to this modern architectural gem tucked among the spruces on Southport Island. The newly renovated house is full of fun angles and expansive windows and is cantilevered over a granite ledge; think Frank Lloyd Wright meets Dr. Seuss. Two master suites (one 1st floor, one 2nd floor), a bunk room and a 4th Queen bedroom. 3.5 luxurious baths.

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).

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.

Cottage at Island Point; Charming Coastal Retreat

The Cottage at Island Point – Southport Island, Maine. Come experience the charm of coastal island living at this serene Southport cottage. Nestled in the peaceful Newagen community, The Cottage at Island Point feels like stepping into an Edward Hopper painting—where life slows down, sea breezes fill the air, and the soothing sound of buoy bells will be your evening soundtrack.