Holiday rentals in Friendship

Romantic A-Frame cabin in the woods

Stay at Hidden Pines Cabins. Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

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.

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.

Sauna+Near Beach+Pond+Outdoor Shower+Fire Pit

Relax at your own private forest retreat! * Private Cedar Glass Sauna * Minutes Reid State Park Beach & 5 Island🦞 * Private Outdoor Shower * Private Fire Pit w/S'mores * 100% Cotton sheets/towels * Rain Shower & Heated Bathroom Floor * AC/Heat * SmartTV & Record Player w/Vinyl * Fast Broadband Wifi *Pine Cabin is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart and separated by a privacy screen and natural landscaping.

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 :-)

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.

Seal Ledge Retreat

Slow down and immerse yourself in the splendor of the St. George river and midcoast Maine. Perched on a ledge among spruces, you'll see seals play, bald eagles hunt, and fish school with the shifting tides. Catch mackerel and striper off the dock. Listen to the whir of hummingbirds and honeybees in the garden and owls call in the moonlight. Watch lobstermen haul their traps. Eat produce fresh from the garden. Experience Maine at its finest!

Cove Watch Cottage - Summer Booking Now

This newly renovated cottage located on a quiet road in Friendship gives you the peace to relax and unwind while enjoying waterfront views and being just a short walk down the street from Walker’s Beach! Inside offers opening living with a full kitchen, living room, and dining area where a separate queen bedroom leads to a full bathroom with washer and dryer.

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.