House holiday rentals in Friendship

Cozy Cottage on the Penobscot – Panoramic Luxury!

Escape to your private waterfront retreat where tranquility meets luxury. Our Coastal Maine Cottage style home rests on a granite ledge that disappears twice daily with the tide. Enjoy a sun-filled interior with cherry floors, a gourmet kitchen, and a private deck for sunrise coffee or evening wine. Wake to sweeping Penobscot River views & unwind by the fire pit at river’s edge. Just 10 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

Family · Value · Getting around

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.

Family · Location · Air conditioning

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!

Family · Value · Kitchen

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.

Family · Location · Pets

Downtown-Walk to All Things Rockland

Cute, convenient, and clean recently renovated 1930’s cottage has two bedrooms, sleeps 4, a private backyard, and is within walking distance to downtown, restaurants, nightlife, co-op & supermarket, museums, shops, art galleries, Harbor Park, ferry and the waterfront. Enjoy off-street parking and an ocean view with the sun glistening off the harbor at the end of the street. This is a perfect home-base for a coastal Maine vacation and festivals. Discounts offered for weekly and monthly stays!

Family · Value · Biking

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba

Waterfront Retreat with Gorgeous Views Stunning 3-bedroom, 2-bath home perfect for multi-generational gatherings. Features an open-concept layout, chef’s kitchen, 1st-floor bedroom and bath, 2nd floor with 2 bedrooms and 1 bath. Kayak from your backyard, hike nearby trails, or swim in Damariscotta Lake just a 5-minute walk away. Stay connected with high-speed fiber optic WiFi. Close to charming Newcastle and Damariscotta shops and restaurants. A true oasis for nature and relaxation lovers!

Value · Family · Backyard

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

Location · Family · Checkout

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 :-)

Value · Family · Outdoor spaces

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!

Location · Family · Cleanliness

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.

Family · Location · Sleep quality

Cottage on the sea

The Cottage rests directly on the sparkling shores of Muscongus Bay in Bremen, Maine. This serene retreat invites you to swim, dine, and unwind as seabirds call, seals play, and lobster boats pass. Inspired by Scandinavian elegance, the home offers privacy and calm, with a private beach and direct access to the waters of the bay —perfect for a morning swim, a peaceful paddle, or simply soaking in the beauty of the Maine coast.

Value · Location · Hospitality

Coastal Maine Retreat · Fire Pit · Walk to Harbor

Tucked into the woods of Round Pond, one of Maine's most beloved working harbor villages, The Round Pond Getaway at Moxie Cove is your base for the best of Midcoast Maine. Walk five minutes to the water, spend evenings around the fire pit, and wake up to nothing but birdsong on the screened porch. Pemaquid Lighthouse, fresh lobster at Muscongus Bay, and the Coastal Maine Botanical Gardens are all within easy reach.

Family · Location · Sleep quality