Vacation rentals in Friendship

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!

Round Pond Crows Nest Brand new and ready for you!

Newly renovated efficiency apartment with exterior entrance. Roomy bed/living room, kitchenette, private bathroom w/ shower. Comfy bed, a table for two looking out at the big maple treetop (with a few hints of the ocean beyond), kitchenette has a bar sink, fridge for your leftovers/bevys, and a microwave to heat them up! It’s on the 3rd floor, so you’ll be getting your workout! Red chairs on the front yard are for guest use- enjoy the fresh air and ocean breeze! Very clean, bright space.

Lobsterman’s Lodge- Working Waterfront Marina!

Spectacular water views from every window in this 900 sq. ft. 2nd floor apartment built atop a stone seawall on Muscongus Bay. Spacious & affordable home-base in the heart of the Pemaquid Peninsula. You are renting the whole 3 bedroom 30’ x 30’ apartment at Broad Cove Marine. The space includes 3 water-view bedrooms, bath, a large living room with high speed internet, and a well-equipped eat-in kitchen. For a truly authentic Maine maritime experience, Lobsterman’s Lodge is the place to stay.

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 :-)

Private tree-top loft 5 minutes from Damariscotta.

Relax in this cozy loft with a light-filled deck overlooking the woods, but just five minutes to downtown Damariscotta. This brand new loft above our barn is cozy with all you need for a perfect vacation. You can relax with your morning coffee above the trees. It has an indoor toilet, sink and breakfast bar and outdoor shower. We’re a semi-retired couple and love to share our 62 acres property with stream and meadow. There are quite a few stairs to the loft.

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!

Modern 1-BR I Wooded Retreat I Mid-Coast Maine

Escape to your perfect Midcoast Maine base camp—just 5 min to Damariscotta/Newcastle & 1 hr 6 min to PWM. Enjoy forest views, modern comforts, and easy access to the coast. • King bed + ensuite • Fully equipped kitchen + charcoal BBQ • Vaulted ceilings, wall of windows, open layout • Private deck, fire pit • WiFi, laundry, parking • Generator (2024) for year-round comfort Ideal for foodies, outdoor lovers & oyster fans!

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.

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.