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Sloop Days Oceanfront Retreat

Welcome to Sloop Days at Naughty Pine in Friendship, Maine! Overlooking Friendship Harbor, this year-round artist retreat offers a serene oceanfront escape. Surrounded by the beauty of lobster country & two working lobster wharves. Friendship is known for its lobster-fishing heritage, scenic nature preserves, and attractions like the Sloop Society's Festival & History Museum. Nearby dining & groceries provide everything needed for an inspiring getaway. Book now to experience Friendship's charm.

Cozy Style Harbor Master’s One Bedroom Cottage

This memorable cottage is anything but ordinary. Waterfront cottage situated in Hatchet Cove. So much to see and do, just a short drive to experience Damariscotta, Whale Watching, or a day at Pemaquid Beach, explore Boothbay or Rockland Harbors. This quintessential one bedroom cottage is one like no other with all the comforts of home. If you’re a lobster lover then this is the place to be. A short walk to our wharf to fetch your fresh lobsters and steam them right next to your private deck.

Captain's Quarters

Welcome to Captain's Quarters, a charming home in Friendship, ME built by a local boat builder. With nautical flair and a cozy feel, it's nestled on a private lot with a small stream and forested backyard, a couple minutes from the main road and a public boat launch into the harbor. There are 3 bedrooms (one with an office), a fully equipped kitchen, and a spacious living area with a fireplace. Colorful decor creates a warm and welcoming atmosphere for relaxation or focus. Book your stay today!

Friendship Coastal Cove Cottage

Beautiful modern country style seacoast retreat. The home is one level with a series of living spaces all oriented to take view of Hatchet Cove in the quaint seaside coastal fishing community of Friendship. Sit back and relax with a book and gaze at the eagles as they soar by or at the beautiful seaside gardens. If you are looking for a peaceful and relaxing retreat along the coast of midcoast Maine, our place will not disappoint. There is a small private local beach up the point.

Maine Waterfront Hideaway

You won't find mobs of tourists here but you will experience a working lobstering village in Maine. Sit back, relax and enjoy the quiet and privacy of 2+ acres at the end of a dirt road with a huge dock located on a tidal cove. Great for family reunions with lots of space and activities for folks of all ages. We focus on making the house comfortable and don't want you to worry about the little things like feet on the couch, water rings on the table or a broken glass. Life happens :-)

Dockside Retreat - 2025 booking quickly

This beautiful, newly renovated home is three bedrooms and two bathrooms, with an open living and dining room waiting to give your family or group of friends the ideal Maine vacation experience! On site parking, a lovely yard, a new sauna on a beautiful deck overlooking the water, nearby fields and steps away from the famous Olson House on one side, you can sit on the deck and overlook the working lobster wharf with fishermen coming and going daily on the other side!

Jameson Point Cottage

Just a short walk away from the town landing, our cozy cottage sits back in the trees, giving you privacy with the ocean in close proximity. Our cottage is a rustic, 3 season building. It is peaceful, quiet and private. The structure is cabin-like, and it has all the conveniences of home including a full kitchen, full bathroom with a washer/dryer, WiFi, a TV, and an office.

Island View Farm

When you are thinking of getting away or just need a rest, come and go glamping on our mini-farm. We would love to share our beautiful view and outstanding sunsets. Nighttime offers amazing stars (when cloudless) and sounds of the country. This family setting is perfect to settle in for a week or two.

Between the Woods and the Water

"Between the Woods and the Water" is located half way from Port Clyde to Tenants Harbor, Maine. These two lobster fishing villages, on the St. George peninsula of Maine, feature a town beach, Marshall Point Light House, and quick access to the ferry to Monhegan Island.