Holiday rentals in Friendship

4.92 out of 5 average rating, 53 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, 135 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, 33 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!

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Flat in Bremen

4.85 out of 5 average rating, 109 reviews

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.

4.95 out of 5 average rating, 104 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, 438 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

4.96 out of 5 average rating, 136 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, 169 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.

4.98 out of 5 average rating, 106 reviews

Guest house in Newcastle

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!

4.92 out of 5 average rating, 286 reviews

Flat in Damariscotta

Fernald's Backside

Fernald's Backside is a sunny, comfortable 2nd floor apartment , tucked behind S. Fernald's Country Store in the heart of downtown Damariscotta. It features a deck with views of the Damariscotta River and Harbor. A one bedroom apartment with ample living space and full kitchen, it can sleep 5 with a double and single bed and a sleeper sofa. Fernald's Backside is Pet free.

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Popular amenities for Friendship holiday rentals

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Other great holiday rentals in Friendship

Flat in Bremen

4.96 out of 5 average rating, 68 reviews

Apartment in Midcoast Maine

EricRating, 5 stars68 months ago

Annette’s place is a great find if you need a place to stay while you explore the Maine countryside. She was great about instructions on finding the house and getting us settled in. Her place was convenient to Damariscotta and the many other wonderful towns in that region of Maine. We will look to stay again if we vacation in the area.

Dome in St. George

4.73 out of 5 average rating, 11 reviews

Historic Cottage w/ Harbor View

BrynaRating, 5 stars9 months ago

We had a great stay at the Tea House. The views are lovely from the deck. We enjoyed Port Clyde and appreciated that it's a little off the beaten track since we were there in the height of the tourist season. You can walk to the ferry that takes you over to Mohegan Island. It was a great find!

5 out of 5 average rating, 10 reviews

Home in Bremen

Authentic Maine Harbor 5 Bedroom Home

RandallRating, 5 stars8 months ago

The house was exactly what we were looking for: relaxing with great views. The marina with fresh seafood within walking distance was icing on the cake.

4.94 out of 5 average rating, 81 reviews

Flat in St. George

Saint George Peninsula Retreat

ElaineRating, 5 stars4 weeks ago

We’ve stayed here many times. It’s a perfect location in St George and to Rockland. The place is decorated so beautifully and is spotless. Kristine is so easy to communicate with and is next door if needed. One our favorite properties.

5 out of 5 average rating, 42 reviews

Guest house in Cushing

The "Fish House": Salt Water Cove Carriage House

JackRating, 5 stars8 months ago

The Fish House was the perfect getaway! Located in a quiet, private neighborhood, the house has a cozy living room with a great view of the water and a sufficient kitchen and bedroom for 2 - the Adirondack chairs by the water and tennis courts down the road were huge bonuses. Chris and Bill (and Tilly) were extremely welcoming and communicative before arriving and throughout our stay. This place is a hidden gem and I’d highly recommend it!

Home in Waldoboro

4.84 out of 5 average rating, 190 reviews

Thistledown Farm's Pennysworth - An 1800's barn.

EstherRating, 5 stars4 months ago

We really enjoyed our stay at Penny’s house! The barn is absolutely beautiful. Please be aware that this is not a private home, even though it’s listed as such. Penny is clear in the description that she lives on the ground floor, and the kitchen and living room are shared spaces. That being said, if that’s what you’re expecting, this is a charming stay and a great base point for exploring the area. Our dog had an absolute blast playing in the yard and we deeply appreciated Penny’s hospitality.

4.93 out of 5 average rating, 204 reviews

Cabin in Boothbay

Peaceful & private waterfront cabin

VeraRating, 5 stars1 week ago

This is our fifth consecutive year of vacationing at the McConnell cabin as a family of three. Hopefully to many more years! This is a very special place. I continue to be grateful to the McConnell family for sharing it and putting so much care and love into making it a welcoming and comfortable oasis.