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Holiday Rentals in Winterport

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    Don't let other travellers get your favourite Winterport area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 25 Rentals in Winterport
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    The following rentals are within 25 kilometers of Winterport.
    Dedham
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    NEW! Lovely 4BR Sandy Point House Close to Beach1 / 26
    (1)Excellent
    Sandy Point
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Dedham
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Verona Island Retreat - Private Pool!1 / 8
    (1)Excellent
    Sandy Point
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Satellite TV
    • Internet Access
    • Parking
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 August 2015
    Everything that you could possibly need was available and it was a great location for side trips, including the lobster fest.
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    About this property
    This newly renovated 3700+ sq ft ft farmhouse and barn w/ 3 car garage rest on over 38 acres of shorefrontage, lush field, pasture and woodland. Beautifully landscapped with gardens, patio, decking and pool. Watch deer and fox with their new babies, or walk the extensive acreage and shoreline....
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    Sandy Point, Mid Coast Maine 04416
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Penobscot
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Penobscot is a tiny, unspoiled town with a great little market (opens at 6:00 am!) and a traditional Maine 'clam shack' where you can purchase live or cooked lobsters. It's an ideal location to explore the Blue Hill peninsula, home to many excellent restaurants, artisans, antique shops, and world...
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    Penobscot, DownEast and Acadia Maine 04476
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lake House Private Beach(Swanlake) Swanville1 / 13
    (9)Excellent
    Swanville
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Waterfront
    • Washer
    • Mountain Views
    • Satellite TV
    • Balcony
    • Central Heating
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This three bedroom lake house is located on a private road with easy access from US RT. 1 & 3 in Belfast. Fully furnished with what you need and also has a Gas BBQ grill on the deck overlooking your own private beach area as well as lawn chairs and picnic table and 2 kayaks . This home has...
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    Swanville, Mid Coast Maine 04915
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Seacroft1 / 19
    (16)Very good
    Stockton Springs
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Parking
    • Satellite TV
    • Patio
    • Grill
    • Internet Access
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2016
    This is a very quiet cabin with a full-width lovely deck and comfortable deck furniture, ideal for long reading sessions. Short rides lead to coastal state parks (Sandy Point...
    Reviewed 3 October 2014
    Cottage was wonderful and hosts were excellent...even laid a fire the first night. Cottage is near enough to multiple water access so we were able to kayak in a variety of...
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    About this property
    Rustic Maine Cottage in a semi-wooded garden landscape with a glimpse of the sea. Perfect for a couple or family with up to two children. Kitchen with range, refrigerator, sink, microwave, toaster and coffee maker. New energy efficient wood stove guaranteed to keep you toasty on the chilliest of...
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    Stockton Springs, Mid Coast Maine 04981
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Swan Lake Waterfront Cottage A/C & Heat1 / 14
    (27)Excellent
    Frankfort
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Waterfront
    • Satellite TV
    • Washer
    • DVD Player
    • Grill
    • Mountain Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Belfast, Searsport, Swanville area......Come spend a week on one of the best beaches on Swan Lake. 100 feet of private sandy beach just a stones throw from your front door. Our three bedroom cottage,(ALL 3 BEDROOMS HAVE AIR CONDITIONING) is completely furnished with everything you need for an...
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    Frankfort, Mid Coast Maine 04438
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Bucksport
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    William’s Wonder is a newly constructed 1,200sqft 1 bedroom plus loft, 2 bathroom cottage located on William’s Pond in Bucksport. The cottage if charmingly decorated with coastal decor and very bright, open and airy. On the first floor you will find a fully stocked kitchen, cozy living room,...
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    Bucksport, DownEast and Acadia Maine 04416
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Private Sandy Beach House sleeps 26,  Weddings, Reunions, yoga retreats  5 star1 / 59
    (8)Excellent
    Sandy Point
    7 Bedrooms, 3 Bathrooms, Sleeps 26 Quick View
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    Amenities & Details
    • DVD Player
    • Housekeeping Included
    • Air Conditioning
    • Mountain Views
    • Internet Access
    • Washer
    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2017
    Our family had lots of space, comfortable and very beautiful. The owners were very helpful in coordinating our trip and meeting our needs. Area is beautiful, lots of different...
    Reviewed 15 August 2017
    Trying to find accommodations for a large group of guests can be difficult at best, but we consider ourselves extremely lucky that we came upon The Retreat House in Stockton...
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    About this property
    The Retreat House Sandy Point, Maine has been a vacation rental for the past 20 years under the name Chateau Mer with over 40 Five Star Review on Trip Advisor. In spring of 2017 new owners have acquired the property and given it a face lift and refreshing. Private sandy beach and waterfront deck...
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    Sandy Point, Mid Coast Maine 04981
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 26
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    Orland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Satellite TV
    • Parking
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Camp Linger is as the name implies....a place where you will want to linger. In fact, you will never want to leave! The cottage is a beautifully remodeled camp on much sought after Toddy Pond. The cottage has been lovingly decorated with a gentle country charm. Beadboard, wood floors,...
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    Orland, DownEast and Acadia Maine 044
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Tranquility on Penobscot Bay Retreat: $200 Discount to "Fall in Love with Maine"1 / 42
    (2)Excellent
    Stockton Springs
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Wi-Fi
    • Mountain Views
    • DVD Player
    • Patio
    • Washer
    • Satellite TV
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2017
    We had a great time staying at Fort Point Cove Cottage. From Darlene's clear and quick communication to the great location and wonderful accommodations, it was all perfectly...
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    About this property
    Off the beaten path nestled along the banks of the historic Penobscot Bay, a sunny, tranquil home offers room to gather with loved ones for renewal and relaxation. You’ll know you’ve arrived at Fort Point Cove Cottage (FPCC) when you catch your breath at the scenery upon entering its front door....
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    Stockton Springs, Mid Coast Maine 04981
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Orland
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Central Heating
    • Washer
    • Waterfront
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Are you in search of a relaxing getaway? If so, then East Orland, Maine is the perfect destination for you! At this 3-bedroom, 2-bathroom home with room for 6, you can truly escape the hustle and bustle of everyday life while enjoying lake activities, historic sites, a charming downtown area, and...
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    Orland, DownEast and Acadia Maine 04431
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Bayside Retreat: Panoramic Views of Penobscot Bay1 / 26
    (3)Excellent
    Bucksport
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Ocean Views
    • Waterfront
    • Central Heating
    • Wi-Fi
    • Mountain Views
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 September 2014
    Darlene is a wonderful host! The house is beautiful with amazing views of the bay. She has create a truly relaxing and peaceful space. There is so much to do in the area...
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    About this property
    Off the beaten path nestled within a mature landscape is The Fort Point Cove Cottage. Panoramic views of Penobscot Bay along with glimmering peaks of Blue Hill Mountain reveal spectacular sunrises and sunsets from this bright open footprint. Rocking chairs on a covered porch, Adirondack chairs on...
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    Bucksport, DownEast and Acadia Maine 04981
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Lakeside Cabin Near Belfast Bay w/ Kayaks & Canoe1 / 42
    (4)Average
    Swanville
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Air Conditioning
    • Grill
    • Mountain Views
    • DVD Player
    • Satellite TV
    • Waterfront
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 January 2017
    This was a typical maine cabin, water is from the lake but the owner provides bottled water. Cabin upkeep (torn screen door) could have been better but the kids had a good time
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    About this property
    Located on a quiet dirt road, this rustic lakeside cottage has charm to spare, with interior pine walls and a woodstove if things ever get chilly. It's fully furnished with two bedrooms, and a single bath. Sleeps five comfortably (plus a pullout couch if needed.) Enjoy crystal clear Swan Lake with...
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    Swanville, Mid Coast Maine 04915
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Brewer
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Private Garden
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 2016
    We spent four days at the Chamberlain house and found it be an excellent and fascinating experience. The house is only minutes from downtown Bangor yet, sitting just across the...
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    About this property
    Brewer birth home of Gen Joshua Chamberlain, commander 20th Maine of Union army battle for Little Round Top in Civil War battle of Gettysburg. Home is situated on Penobscot River. Luxury suite, dining area, living area, furnished and appointed with period antiques. Bedroom suite has two joining...
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    Brewer, Maine 04412
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 3
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    The Riverhouse1 / 35
    (7)Excellent
    Orland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Secure Parking
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Waterfront
    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 June 2015
    We stayed at the River House in mid-June and we enjoyed the quietness, and the comfort of being only one hour from Bar Harbor and Acadia National Park. The owner was very...
    Reviewed 13 November 2014
    My sister and I stayed at the River House late in October. While Mother Nature was cranky in the form of a Nor'easter Dan and the Riverhouse was exactly what we were looking for...
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    About this property
    The 'Riverhouse' located in Orland, Maine is a furnished 2 bedroom Cape. Located on the Penobscot River, the views of the river and bay are dramatic with beach privileges and boat anchorage available. Conveniently located 10 minutes from historic Castine, 1 hour from Acadia National Park, and 45...
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    Orland, DownEast and Acadia Maine 04472
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Holden
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Balcony
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    East of Bangor with its Casino,rest's and summer activities along the Penobscot river; close to the Trenton Lobster Pound and Acadia National Park with the Jorden Pond House(homemade jam,tea and popovers), horseback riding, hiking trails, Cadillac Mtn., Thuya Gardens , whale watching etc. It has 3...
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    Holden, Maine 04429
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Penobscot
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Outdoor Dining Area
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Orland just a few minutes outside of Castine, this newly renovated cottage features long views down the ocean river. It is just a few minutes walk to your own private beach. Nicely decorated with a large comfortable deck. Bedrooms located on second floor. Bathroom located on first. A...
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    Penobscot, DownEast and Acadia Maine 04476
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The Round House on 53 Private Wooded Acres1 / 30
    (3)Excellent
    Swanville
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Sauna
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Central Heating
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 March 2016
    The Round House was above and beyond what I was expecting. The house is beautiful. The trails on the property are awesome. Everything about the house was fantastic and the Tall...
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    About this property
    Sleeps up to 10 people : 3 Bedrooms (1K-1Q-3F), Game Room, 2 baths, Sauna Looking for a Getaway? Our home is a perfect place for a quiet weekend retreat or fun filled family vacation. Enjoy the open concept of this custom built round house in beautiful wooded views throughout. The long tree...
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    Swanville, Mid Coast Maine 04915
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Cape Jellison Waterfront!!  Incredible Views!!1 / 12
    (14)Very good
    Stockton Springs
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Satellite TV
    • Ocean Views
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 August 2016
    The best part of this place was the view. Walk out on to the back deck and just go "WOW" It's incredibly peaceful and quiet here The mosquitos can get thick around dusk...
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    About this property
    Come sit on the deck and enjoy the incredible views of this recently renovated waterfront property!! This home sits on 450 feet of private waterfront and is about 75 feet from the high water mark and has easy beach access. Spend your days enjoying the view or enjoy days trips to nearby Searsport...
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    Stockton Springs, Mid Coast Maine 04981
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    SWAN LAKE COTTAGE, FALL FOLIAGE, PRIVATE BEACH, DOCK1 / 15
    (10)Excellent
    Swanville
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    • Private Garden
    • Satellite TV
    • Grill
    • Patio
    • Waterfront
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    This sweet little cabin had it all! The perfect location for all lake activities and all the necessary amenities - kayak, SUP, dock, floating dock, fire pit etc... The cabin...
    Reviewed 2 weeks ago
    Sitting out on the porch or under the tree overlooking the lake was so restful. Our dog loved running full speed off the end of the dock and diving into the water to chase his...
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    About this property
    Located on Swan Lake, this one bedroom cottage has a queen size bed with a separate day bed and a sleep sofa. It is located on a private road with easy access from US RT. 1 & 3 to the Mid-coast area and Bar Harbor. Everything you need is here, including your own private sandy beach, a swim float,...
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    Swanville, Mid Coast Maine 04915
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    Beautiful Lake Front Cottage on Swan Lake1 / 20
    (14)Excellent
    Swanville
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Grill
    • Waterfront
    • DVD Player
    • Parking
    • Mountain Views
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come spend a week at one of the best kept secrets on Swan Lake. Our cottage has a private dock, swim float, kayak and canoe (exclusively yours for the week). Our two bedroom cottage is completely furnished with everything you need for an enjoyable week at the lake. We also supply cable and...
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    Swanville, Mid Coast Maine 04915
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Maine. Lovely Cottage on Penobscot Bay1 / 20
    (12)Very good
    Penobscot
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Waterfront
    • Satellite TV
    • DVD Player
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 2017
    We booked the cottage as a launching point for our Maine adventures from Rockland, Acadia, Deer Isle and all points in between. This place was great. It was quiet and out of the...
    Reviewed 4 June 2017
    This was our second, but not the last visit to this cottage. Our first was in June 2015, and we loved both weeks. Wonderful cottage, easy access to local lakes, blueberry farms...
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    About this property
    Our cottage sits on a small bluff directly overlooking Penobscot Bay. About 15 feet from the cottage deck is our private stairs, leading to the water's edge. Maine coastline is more rocky than sandy -- our "beach" is perfect for rock scrambling. And there is a little dock at the foot of the...
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    Location Information
    Penobscot, DownEast and Acadia Maine 04476
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Penobscot
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Red Camp is a 1 bedroom plus loft, 1 bathroom cottage located on the banks of the Bagaduce River. The cozy, rustic camp sleeps 4 with one queen bed and two twin beds. The kitchen is equipped with dishes and cookware and all linens are provided. While the inside of the camp is charming it’s the...
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    Location Information
    Penobscot, DownEast and Acadia Maine 04476
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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