Experience coastal charm at the Pine Cliff Dweller in Southport, ME.

Pine Cliff Dweller: Classic Coastal Comfort and Panoramic Views

Perched on a cliff overlooking the entrance to Boothbay Harbor and the islands of the Atlantic, Pine Cliff Dweller is a treasured family home ready for your next memorable Maine vacation. This cozy, traditional cottage serves as a popular home base for both adventurers and those seeking a quiet retreat, offering a warm and inviting atmosphere that feels like a true home away from home.


Charming Features
Panoramic Ocean Vistas: Watch the world go by from the dining room, which features three walls of windows overlooking the ocean, your private dock, and surrounding islands.
Classic Maine Ambiance: Enjoy the cozy feel of this non-minimalist retreat, complete with a working, wood-burning fieldstone fireplace that serves as the heart of the home.
Master Suite with A/C: The second-floor master bedroom features a king bed, panoramic views, and air conditioning to ensure comfort on warm summer nights.
Private Dock and Float: Witness the activity of the harbor firsthand, from elegant yachts to hardworking lobster boats. You may even spot porpoises, migratory shorebirds, or the occasional whale. Love fresh seafood? You can connect with local lobstermen for dockside service right on your private dock!
Inviting Living Spaces: The open layout is filled with natural light thanks to large windows and sliding doors, making it easy for guests to gather in the family room or living area.
Perfect for Groups: With a bedroom and full bathroom on each floor, this home is ideal for two couples or small families. For larger gatherings, the neighboring cottage, Piffi Biff, can be rented in conjunction for a multi-family getaway.


The Details:

Minimum Stay: Weekly (Saturday-Saturday) during June, July, and August; 4-night minimum in the Fall. Stay for a week or longer during the Fall to receive a better value on your booking! BEDROOMS: (1) King (Master with A/C), (1) Queen. BATHROOMS: (2) Full bathrooms, both featuring tub/shower combinations. DOGS PERMITTED? No, pets are not allowed at this property. LINENS & TOWELS INCLUDED? Yes, linens and towels are included in your reservation.


Explore the Region
Southport Island Exploration: Discover the quiet charm of the island, including the Southport General Store, Hendrick's Head Beach, and the scenic views along the shore.
Iconic Sightseeing: From the cottage, you have a front-row seat to views of Burnt Island and Squirrel Island.
Boothbay Harbor Entrance: Enjoy being at the gateway of the region's most famous harbor, just a short drive from downtown shops and restaurants.


Book your classic Maine retreat at Pine Cliff Dweller 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.