Holiday rentals in Friendship

4.93 out of 5 average rating, 54 reviews

Family Escape w/ Kayaks, Fire Pit, & Water Access

Slow down & reconnect at our family-ready farmhouse near MidCoast Maine’s top towns. With 2 kitchens, kayaks, Peloton, fire pit, toys & more, it’s perfect for cozy nights in or adventures out! Spacious, peaceful & thoughtfully stocked for all ages “Completely blown away...this little gem has everything a family or two could want!” HIGHLIGHTS ✓ On-site fun for multi-gen groups ✓ 2 kitchens + great room = perfect group flow ✓ 11 private acres ✓ Just mins to iconic coastal Maine spots like Camden

4.99 out of 5 average rating, 138 reviews

Cabin in Georgetown

Sauna+Near Beach+Pond+Outdoor Shower+FirePit+A/C

Come relax at Pine Cabin, one of two cabins on 8 acres with a pond minutes from one of the best beaches in Maine. Unwind in your private outdoor cedar glass sauna w/forest views & refresh in our seasonal outside shower! * Minutes to Reid State Park & 5 Island🦞 * Fire Pit * Family Own & Run * Gas Grill * Private Bedroom w/Queen Bed * Loft w/Queen Bed & Record Player * Rain Shower * Custom cabinets & couch * Screen porch * AC/Heat * EV charger * Fast Wifi * Beach Gear * Smart TV * Generator

Place to stay in Friendship

5 out of 5 average rating, 47 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, 34 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, 132 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.

4.95 out of 5 average rating, 106 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 :-)

4.98 out of 5 average rating, 441 reviews

Guest suite in Rockland

5 Laurel Studio private entrance STR20-69

Open concept small studio, private patio and entrance, full kitchen. *SHARED wall between studio and main house, therefore some shared noise. 2 minute walk to the ocean , Lobster and Blues Festivals. A small swimming beach is a 5 minute walK, 5-10 minutes to the Farnsworth and CMCA museums, Strand Theater, restaurants, antiques shops & galleries. ALSO NOTE we do not have television. We have wifi but you must bring your own device . EXEMPT FROM ACCEPTING SERVICE DOG

4.95 out of 5 average rating, 138 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, 172 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.

5 out of 5 average rating, 86 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.