Vacation rentals in Friendship

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.

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!

Candlelit island cabin on secluded Midcoast shore

A shorefront cabin for two on Midcoast Maine island oyster farm; boat ride to and from Friendship Town Wharf provided. Bring your taste for off-grid glamping adventure. No plumbing (outhouse, rain-barrel showers). No electricity (candles and headlamps; solar phone-charging nearby). Otherwise comfortable and romantic, with excellent bed and linens. Fire pit, private beach, mossy trails, blueberries, kayak adventures, dark night skies, oysters, peace, quiet. See also: Morse Cove Oysters on insta.

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.

Glass Wall Waterfront Hot Tub Fireplace Tiny Home

Wake up to rushing waterfalls right outside your glass wall in this romantic waterfront tiny home in Norway, Maine! Private hot tub with river views, see-through gas fireplace, cozy raised queen bed overlooking the water, outdoor shower, hammocks, and direct access to hiking trails. Total privacy—no neighbors in sight. Modern kitchen, heated floors, fast WiFi, and thoughtful touches for couples or solo escapes. Romantic getaway near Sunday River skiing, golf & Maine adventures. Nature's oasis

Kens Cottage in Round Pond ME

Take it easy at this unique and tranquil getaway. Round Pond is a very special village in Muscongus Bay. It is comprised of a large natural cove filled with an array of boats from working lobster boats to gorgeous pleasure crafts. Located on the Northern Point of Round Pond Harbor the views on the property are stunning. You could be taking in the activity of the harbor in one direction, then watch sailing classes and lobster boats working off Loud's Island in another or just gaze down the bay.

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 - few summer openings remain

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!

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE does not have a hot tub but guests may reserve the sauna, which is close by and private. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Timeless Tides Cottage

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.

Maine-Coast Waterfront: Families and Friends.

Reunite with family or friends in this lovingly restored, 3,500 sq. ft., 2.2 acre, Civil War-era farmhouse and studio on the Maine Coast. * Glorious views. * A 24- by 26-foot private indoor studio and office * A 30- by 40-foot private outdoor beach deck & shed. Full marine dock, launch ramp, and moorings. Back-up power. Professional management. Ideal for 8 to 12. Fully Insured. NO EVENTS, please.

Tall Spruce Cottage

Comfortable cottage in the rural town of Cushing, known for its natural beauty that inspired many of Andrew Wyeth's work including "Christina's World" and the Olson house. The cottage is on the same property as my home. The cottage is a one bedroom space with a full kitchen and bathroom. There is also a woodstove if needed during the colder months. Laundry is available downstairs.