Pinecroft: Spacious Southport Getaway with Association Dock Access, Patio & Mooring Available

Pinecroft: A Classic Summer Haven on Southport

New for 2026! Welcome to Pinecroft, a quintessential Maine summer cottage that captures the pure essence of island life. Tucked away in a peaceful Southport association—right next door to Griffin Cottage and just a short walk to Pine Cliff and Piffi Biff—this charming multi-story home is designed for classic coastal relaxation. Boasting an incredibly spacious layout, a wrap-around porch, and community waterfront privileges just steps away, Pinecroft is the perfect setting for families and groups to gather and make lasting summer memories.

Charming Features
Grand Open-Concept Living: The heart of the home is a massive, light-filled living and dining area that spans nearly half the footprint of the first floor. Featuring soaring cathedral ceilings, it is the ultimate space for everyone to gather comfortably.
The Three-Side Porch: Step outside onto a massive porch that wraps around three sides of the cottage, offering a peaceful spot for reading, enjoying the shade, or listening to the rustle of the pines.
Scenic Patio Dining: Fire up the grill on the home's beautiful outdoor patio, which features pretty water views and plenty of space for memorable al fresco dinners under the Maine sky.
Balcony Overlook: A staircase leads from the main living area up to a beautiful second-floor balcony that overlooks the great room below, connecting the upper-level bedrooms with the social heart of the house.
Association Dock Access: While the property does not have direct water access, the neighborhood association dock and float are located just two doors down, making it incredibly easy to get down to the shoreline.
Bring Your Boat: For the boating enthusiast, a private mooring ball is available for guest rental right in front of the cottage, accommodating boats up to 20 feet.
Convenient Modern Amenities: Enjoy the major added bonus of an in-home washer and dryer—a rare and highly convenient luxury for a classic cottage located so close to the water.

Minimum Stay: 4-Night Minimum. Stay for a week or longer to receive a better value on your booking!
BEDROOMS: 4 Bedrooms: (1) King, (1) Queen, (1) Double (Main Floor), (2) Twins. Sleeps 8.
BATHROOMS: 2 Full Bathrooms (Main floor bath features a tub/shower combo).
DOGS PERMITTED? No, pets are not allowed at this home.
LINENS & TOWELS INCLUDED? Yes, linens and towels are included in your reservation.

Explore Southport Island
Coastal Maine Botanical Gardens: Just a short drive off the island (2.5 miles), explore miles of scenic trails, midcoast flora, and the famous giant wooden trolls.
Pine Cliff & Piffi Biff: Enjoy the convenience of being within easy walking distance to these beloved local island landmarks.
Hendrick's Head Beach: Pack a picnic and spend the day searching for sea glass at Southport’s beautiful public sandy beach, overlooked by its historic lighthouse.
Robinson’s Wharf: Drive just a few minutes down the road to cross the bridge and enjoy fresh lobster rolls on a bustling, working waterfront deck.
Book your classic island getaway at Pinecroft today!

COTTAGE CONNECTION Vacation Rentals. Privately Owned. Professionally Managed. Trusted since 1993. Cottage Connection was one of the first vacation rental companies in the Midcoast region of Maine. Since being founded by Jeff and Audrey Miller in 1993, Cottage Connection has been trusted by homeowners and vacationers alike to connect each family with the perfect vacation cottage.