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Holiday Homes in Rockland

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    All 34 Rentals in Rockland
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    Sensational 5* Apt. in 1862 Sea Captain's House1 / 14
    (14)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Luxury 5* Apartment in 1862 Sea Captain's House1 / 16
    (10)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Spacious lake house with dock and sandy beach1 / 24
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Marshall Point retreat in coveted Port Clyde1 / 12
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed 3 November 2017
    The view from Little White Caps is lovely, over the bay with a sunrise in the morning and lobster boats checking their traps. It was warm enough to keep the windows open at...
    Reviewed 9 August 2017
    The location is wonderful. Easy stroll into town or to the lighthouse. The view from the deck, bedroom and living area is gorgeous. There is a nice backyard area. Port Clyde is...
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    About this property
    White Caps Guest House, sits on historic and beloved Marshall Point Road in Port Clyde – As part of a family compound, it overlooks both Muscongus and Penobscot Bay and provides stunning views of the islands, like Monhegan, that dot the horizon. Cherished by family for years, White Caps and Little...
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    Rockland, Mid Coast Maine 4860
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Smoking allowed
    About this property
    Michelle Lane is a custom-built 3 bedroom, 2.5 bath free standing condo offering the benefits of a hotel or resort with the privacy and comfort of a private residence. The Village at Rockport is newly built neighborhood between the towns of Rockland, Camden and Rockport. This well planned and...
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    Rockland, Mid Coast Maine 4841
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Waterfront
    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    Harrington Cove Cottage is located on 150 feet of easily accessible water. Located between Tenants Harbor Village and Spruce Head, this 2 bedroom, 1 bath cottage was recently and tastefully renovated. Think classic cottage meets modern design – all situated to take full advantage of the gorgeous...
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    Rockland, Mid Coast Maine 4860
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Rockland Harbor Watch is the answer to what a lot of visitors to the Midcoast area want – a property that is in town, walkable and where is a car isn’t necessarily needed. Rockland Harbor Watch is the newly renovated first floor of a classic Sea Captain’s House in the coveted and up and coming area...
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    Rockland, Mid Coast Maine 4860
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Think peaceful, tree laden haven with the sounds of lobster boats humming in the distance when you think of Settlers Cottage in Cushing. Originally built by the owner’s grandfather, this adorable cottage has recently been renovated. All of the original charm remains but you no longer have to “rough...
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    Rockland, Mid Coast Maine 4572
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Sleeps 8 in 4 bedrooms; 1 full bathroom and 1/2 bathroom Owls Nest has been in the Creamer Family for generations — it is well-loved, embellished by family memories, neat and comfortable. It feels like a throw-back to simpler times when vacation homes weren`t about being exactly like your...
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    Rockland, Mid Coast Maine 4843
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Consider yourself lucky if you get the opportunity to stay at Clark Point – it truly takes your breath away. Even those of us who live here year round are mesmerized by absolute natural perfection this property provides. Located on Clark Point, a beautiful section of the Clark Island area of the...
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    Rockland, Mid Coast Maine 4860
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Etta's Cottage was built in the 1960s by Etta and Almond Hall on land that had been owned by their family for 200 years. The cottage, which is a everything a summer cottage along the shores of the St. George River, a tidal, saltwater riverway, should be...and shouldn't be. Although the cottage was...
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    Rockland, Mid Coast Maine 4860
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Oceanside Upscale Living at C'est LaVie -Walk to Attractions Restaurants & Ocean1 / 11
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Grill
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    • Ocean Views
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    Smoking allowed
    Reviewed 16 August 2018
    Perfect for individual comfort . Nicely planned out and decorated.Cute side yard to hang in for early evening cocktails. Big eat in kitchen for your group to gather in. Comfy...
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    Relax and renew in our spacious clean home with three bedrooms and all new beds! Oceanside 3 Bedroom upscale home steps away from the Atlantic Ocean and Route 1. This Greek Revival home has original expansive gorgeous woodwork installed in 1850! The original wide pine floors and high ceilings with...
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    Rockland, Mid Coast Maine 04841
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    For more than 150 years, the Captain’s Quarters has looked out over Rockland Harbor. A townhouse in the truest sense of the word, this duplex was originally built for two sisters who wanted to live and raise their families next to each other. Located in the heart of Rockland, Captain’s Quarters is...
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    Rockland, Mid Coast Maine 04841
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Homeport is aptly named — this stunning house is truly a home away from home. Situated on the shores of the Weskeag, a beautiful salt waterway, Homeport is nestled in woods offering peace and quiet and privacy. The house is situated on over 2 acres with 350 feet of water front — watch wildlife from...
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    Rockland, Mid Coast Maine 4858
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Downtown 'Namastay'1 / 9
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Smoking allowed
    Reviewed 15 August 2018
    We thoroughly enjoyed our stay. The house is located within walking distance to restaurants, coffee shops, bars, and the downtown area.The house was clean and comfortable.
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    About this property
    Heart of downtown home 3 blocks from festivals, boardwalk, restaurants, movies, gelato. Walk to everything! Beautifully decorated, the house features a sunroom, a baby grand piano, large bedrooms, 2 bathrooms, and raised gardens. Access to a shed on property. Two parking spaces available off street...
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    Rockland, Mid Coast Maine 04841
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Maple Street1 / 12
    (5)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed 9 July 2018
    We didn’t do enough research to know that Rockland is a small Maine town that rolls up its streets at 9:00 p.m.! Thus, if you go touring during the day and get home late, you’d...
    Reviewed 2 August 2015
    We were a little nervous about sending payment in full to an individual (instead of a company) but Steve was more than happy to answer questions and reassuring about that. The...
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    About this property
    Phase Two Completed. It just keeps on getting better. This stunning and beautifully furnished two bedroom unit has just been completed. A second floor apartment close to downtown Rockland and in a nice area of town. There is a large living/dining room with cable TV and stereo. This is a...
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    Rockland, Mid Coast Maine 04841
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Plot your next break at Prosehaven                               (STR R18-60)1 / 24
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed 10 May 2018
    Prosehaven was my first stay in Maine and it won’t be my last. I loved the town of Rockland and the artistic community that lives there. I had the pleasure of making the First...
    Reviewed 23 November 2016
    The rental portion of this Rockland ME property is entirely private and self-sufficient, it's beautifully furnished, with a terrific kitchen, living room, two upstairs rooms...
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    About this property
    This writer’s 1803 home in lovely Rockland neighborhood is a leisurely 10-minute walk to downtown and the waterfront. Thoughtful renovations have given the rooms renewed life, with fresh paint on the walls and floors, cottaged furniture, and new beds with crisp linens. The charming space offers a...
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    Rockland, Mid Coast Maine 04841
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Classic Maine waterfront cottage on stunning Crescent Beach1 / 33
    (2)Average
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Reviewed 22 October 2016
    I visited in the fall when the foliage was beautiful. The property is right on the water with incredible views of the ocean and nearby islands. Quiet, secluded neighborhood...
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    About this property
    This seasonal cottage, also known as Crockett`s Cottage, sits on a parcel of land just 25 feet from the water`s edge. Like all proper oceanfront summer cottages, it is oriented towards the water, with beautiful views of the beach and the open ocean from almost every room. A nicely landscaped lawn...
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    Rockland, Mid Coast Maine 4854
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Sleeps 4 in 2 bedrooms and 1 sunporch; 1 full bathroom and 1 half bathroom Your peaceful cottage is in the middle of it all — ideal for day trips. Lupine has been renovated beautifully — the downstairs is open-concept with high ceilings, hardwood floors, a large kitchen, breakfast bar, dining area...
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    Rockland, Mid Coast Maine 4854
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Private and peaceful, located on 3 private acres at the head of Seavey`s Cove.1 / 32
    (1)Terrible
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Sleeps 4 in 1 bedroom; 2 full bathrooms (1 with shower) Lettie`s Cottage is located on three private acres at the head of Seavey`s Cove in Tenants Harbor. Very private and peaceful, the Maine vacation rental cottage is surrounded by water on three sides and is 75 feet from the water`s edge. It...
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    Rockland, Mid Coast Maine 4860
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    Leave your car in our driveway and enjoy all Rockland has to offer. Our 1863 two bedroom home is on a quiet residential street just 2 blocks from Rockland's Main Street. Excellent restaurants, waterfront, unique shops, galleries, museums and live performance venues. The space You will love this...
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    Rockland, Mid Coast Maine 04841
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    The Boat House is a lovely and accurate reproduction of the lakeside cottage the owner’s family spent countless summers in when he was a boy. Recently renovated to include a wing for a private bedroom and laundry closet, this is a true year round cottage with all the comforts of home. This is a...
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    Rockland, Mid Coast Maine 4563
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    This wonderful 1940s renovated cottage is about 1500 square feet and is furnished with antiques and very comfortable furniture. Situated on the St. George River, the cottage sits 20 feet back from Wiley Cove at the end of a 1/2 mile dirt road in Cushing, about 5 miles from Thomaston. There are...
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    Rockland, Mid Coast Maine 4855
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    If you would like to ability to walk more and drive less on your vacation, Ledgeview may be just what you are looking for. This truly stunning and beautifully renovated 1870’s farmhouse sits atop a granite ledge at the quiet end of Watts Avenue. Surrounded by a well-manicured and sprawling lawn,...
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    Rockland, Mid Coast Maine 4860
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Owl`s Drift is located in the beautiful seaside village of Camden. It sits snugly on Pleasant Street, one of Camden`s quaint tree-lined side streets. Truly an in-town retreat with private gardens and a courtyard bounded by evergreens — guests may never suspect the village is just a five-minute walk...
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    Rockland, Mid Coast Maine 4860
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Executive Family Home. Meticulously restored antique 3 bedroom, 2 bath home with wood floors throughout. Large eat-in kitchen with new appliances, including washer and dryer. First floor has a front porch with antique stone floor and sun room with two sets of double french doors which open onto a...
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    Rockland, Mid Coast Maine 04841
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Location/Grounds: Montgomery Cottage is located in the historic and artful city of Rockland in a quiet neighborhood down the block from the harbor, a park, the Coastal Children's Museum, and the Sail Power and Steam Museum. It is six blocks to the galleries, shops, and restaurants on Main Street....
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    Rockland, Mid Coast Maine 04841
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Sleeps 2–4 in one bedroom and 1 futon; 1 full bathroom Little Egg Cottage sits directly on North Pond in Warren. With privacy and views abounding, this newly-constructed cottage has all the modern amenities and comforts of home without sacrificing the classic lakefront cottage and cabin-styling and...
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    Rockland, Mid Coast Maine 4864
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    With a Tempurpedic bed, large bath tub, and cozy living room, any couple will love this sweet apartment. Walking distance to town, The Good Tern Co-op, The Breakwater Lighthouse, Shopping, Grocery Stores, Gas Stations, and The Samoset Resort and Healthclub. You have ocean views from the kitchen and...
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    Rockland, Mid Coast Maine 04841
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Rockland 'Harborfront' - across from Samoset1 / 21
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • Waterfront
    • Ocean Views
    • Central Heating
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    Pet friendly
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    Reviewed 15 October 2017
    This house is handsome, clean and well-equipped to keep you happy for your stay in Rockland, Me. It is centrally located in mid-Maine, and in the number one location for Lobster...
    Reviewed 1 October 2015
    My family and I have spent many summers in Rockland, Maine. Through the years, we've all aged and this time -- there were two 80 year olds on the trip, so we wanted something...
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    About this property
    The Rockland Harbor House is located directly on Rockland Harbor. The house is 2000 sq ft. and has 3 bedrooms with 2 full baths. The house is located on Samoset road just a short walk to the Rockland Breakwater Lighthouse which is located at the end of Samoset Road. The house is conveniently...
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    Rockland, Mid Coast Maine 04841
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Maine Windward is a beautiful 4 bedroom house located on the outskirts of Rockland near Lake Chickawaukie and in very close proximity to the Samoset Golf Course, downtown Rockland, Rockport and Camden. The house sits on 8 private and wooded acres and was designed for both form and function –...
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    Rockland, Mid Coast Maine 04414
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Sunrise Summit1 / 49
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Reviewed 10 October 2017
    This place has perhaps the most spectacular view of any place we have ever stayed, and we travel extensively. Pictures do not do it justice. The home is unique, well...
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    About this property
    ‘Ocean view’ only begins to describe what this one-of-a-kind Maine vacation rental house is about: ‘best view on the coast of Maine’, ‘you can’t help but feel one with the elements’, ‘no need to go anywhere, its all right here’, ‘unimpeded views exceeding 180 degrees:’ Penobscot Bay, Chickawaukee...
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    Rockland, Mid Coast Maine 04841
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • Cable/satellite TV
    • Skiing: Property Is In A Ski Resort
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    Pet friendly
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    Smoking allowed
    About this property
    Built in 1868, this lovely 3-bedroom, 2-bath vacation rental house exudes New England culture and charm in southern Rockland. This updated home accommodates up to 8 travelers and sits within a 5-minute drive to the dynamic shops, restaurants, and museums in historic downtown. Enroll in a sailing...
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    Rockland, Mid Coast Maine 04841
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    About this property
    Seal Cove is a gorgeous post-and-beam waterfront house with a large lawn sloping down to Wheeler`s Bay. Walk along the shore of Spruce Head Island, watch lobster boats come in after a long day, kayak along the craggy shores of the Maine coast and then return to this stunning house to relax on the...
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    Location Information
    Rockland, Mid Coast Maine 4854
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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