Holiday rentals in Friendship

Place to stay in Friendship

5 out of 5 average rating, 49 reviews

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.

4.97 out of 5 average rating, 38 reviews

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!

Guest suite in Round Pond

4.81 out of 5 average rating, 133 reviews

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.

5 out of 5 average rating, 19 reviews

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.

4.95 out of 5 average rating, 109 reviews

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 :-)

Guest house in Damariscotta

4.95 out of 5 average rating, 100 reviews

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.

4.95 out of 5 average rating, 142 reviews

Home in Cushing

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!

Cottage in South Thomaston

4.95 out of 5 average rating, 176 reviews

Timeless Tides Cottage

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own private 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.

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Home in Waldoboro

4.83 out of 5 average rating, 30 reviews

Peaceful Maine Haven

Rest and relax in this cozy cottage by the sea. Home has new appliances, kitchen, bathroom, flooring, furniture, doors, and paint! Located towards the end of one of Maine's peninsulas, this property is on a quiet road that is perfect for taking a walk or running with lots of sights to see! There is a marsh on one side of the home with birds and wildlife year-round; fox, deer, frogs, turkeys to name a few. Plenty of adventure awaits or cozy up and rest!

5 out of 5 average rating, 88 reviews

Vintage ISLAND farmhouse, BYO boat/kayak. Unique!

A Midcoast Maine island paradise. Bring (or rent) your boat/kayak and taste for adventure. Secluded circa-1850 saltwater farmhouse, 1/4-mile private shore. No plumbing (outhouse, rain-barrel showers). No electricity (candles, lamps, flashlights; solar phone-charging). One mile from Friendship Harbor town landing. Beach, wharf, boathouse, forest trails, blueberries, kayak adventures, dark night skies, lobsters, peace, quiet. Note: Inaccessible at dead-low tide.

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Cottage in Friendship

4.6 out of 5 average rating, 53 reviews

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.