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Winterport Holiday Homes

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    1 / 21
    5 of 5 bubbles (1) Excellent
    Winterport
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    The following rentals are within 25 kilometres of Winterport, Maine.

    1 / 35
    5 of 5 bubbles (7) Excellent
    Orland
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 20
    5 of 5 bubbles (3) Excellent
    Orland
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 11
    2.5 of 5 bubbles (2) Poor
    Brewer
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    Amenities & Details
    • Private Garden
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Brewer, Maine 04412
    4 of 5 bubbles 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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    1 / 18
    5 of 5 bubbles (2) Excellent
    Orland
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Amenities & Details
    • Secure Parking
    • DVD Player
    • Mountain Views
    • Grill
    • Private Garden
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This mountain Cabin is without a doubt the most remote and secluded vacation rental in the region. This is THE place to be if you truly wish to escape the trappings and stresses of “civilization”. This is NOT a typical rental home. It is an off-grid home and powered by solar and wind electricity.... View all property information
    Location Information
    Orland, DownEast and Acadia Maine 04472
    5 of 5 bubbles Reviewed 31 October 2015
    I loved this warm little cabin with quaint upstairs bedrooms. It's situated in the mountain with awesome views. We spent time hiking and truly enjoyed this unique experience. The...
    5 of 5 bubbles Reviewed 6 August 2015
    We rented the cabin for a month with our cats and dogs while we were in between houses. We really enjoyed staying there and our dogs loved being able to stay outside and explore...
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    1 / 26
    5 of 5 bubbles (3) Excellent
    Bucksport
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Ocean Views
    • Waterfront
    • Central Heating
    • Wi-Fi
    • Mountain Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Bucksport, DownEast and Acadia Maine 04981
    5 of 5 bubbles 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 you...
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    1 / 26
    Sandy Point
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Satellite TV
    • DVD Player
    • Patio
    • Internet Access
    • Grill
    • Parking
    • Central Heating
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Gather your loved ones and pack your bags for a rejuvenating Sandy Point getaway when you book this 4-bedroom, 2.5-bathroom vacation rental house that comfortably sleeps 9. Situated in a secluded woodland area just a quarter of a mile from the beach, this splendid home promises a revitalizing... View all property information
    Location Information
    Sandy Point, Mid Coast Maine 04972
    1 / 19
    4.5 of 5 bubbles (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
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Stockton Springs, Mid Coast Maine 04981
    4 of 5 bubbles 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...
    5 of 5 bubbles 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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    1 / 17
    Orland
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • Waterfront
    • Central Heating
    • Parking
    • Patio
    • Washer
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Are you in search of a relaxing getaway? If so, then East Orland, Maine is the perfect destination for you! Here, you can truly escape the hustle and bustle of everyday life while enjoying lake activities, historic sites, a charming downtown area, and beautiful natural scenery. Experience the best... View all property information
    Location Information
    Orland, DownEast and Acadia Maine 04431
    1 / 24
    Stockton Springs
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • Washer
    • Balcony
    • Grill
    • Air Conditioning
    • Patio
    • Internet Access
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Tranquil setting overlooking beautiful Penobscot Bay. Sunny and tastefully decorated, this has been our home for 10 years. Centrally located in mid-coast Maine, our stunning home is near Acadia National Park ( one of the top five national parks visited in the US 43 miles) , 29 miles to Camden... View all property information
    Location Information
    Stockton Springs, Mid Coast Maine 04981
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    1 / 20
    4.5 of 5 bubbles (10) 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
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Penobscot, DownEast and Acadia Maine 04476
    4 of 5 bubbles Reviewed 28 August 2014
    My husband, my daughter, our dog, and I stayed a week at the end of June and had a great time. While not luxurious, you will find everything you need for a relaxing vacation. The...
    5 of 5 bubbles Reviewed 3 June 2014
    Cottage was great. Up on a bluff over the water, it was like being on a boat, with water on 3 sides. Cottage was cute and nicely furnished and as described. Everything worked...
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    1 / 37
    Dedham
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Washer
    • Grill
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This brand new Dedham home boasts a plethora of amenities, from a private dock to a fireplace to a gorgeous deck. It's the perfect summer retreat. You're right near gorgeous Phillip's Lake and the Lucerne Inn and its golf course are only four miles away. Nature's splendor never looked this good.... View all property information
    Location Information
    Dedham, Maine 04429
    1 / 18
    5 of 5 bubbles (14) Excellent
    Swanville
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Grill
    • Parking
    • Waterfront
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Swanville, Mid Coast Maine 04915
    1 / 18
    5 of 5 bubbles (5) Excellent
    Eddington
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Grill
    • Washer
    • Parking
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Wake to the call of the loons and drink your coffee on the deck just steps from the shores of Davis Pond. Enjoy the private dock and spend your days swimming, fishing, paddle boating, or simply reading on the lawn. Gaze across the lake to the surrounding hills for breathtaking views. The open deck... View all property information
    Location Information
    Eddington, Maine 04428
    1 / 12
    Bucksport
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Grill
    • Washer
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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,... View all property information
    Location Information
    Bucksport, DownEast and Acadia Maine 04416
    1 / 7
    Penobscot
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Penobscot, DownEast and Acadia Maine 04476
    1 / 11
    4.5 of 5 bubbles (14) Very good
    Stockton Springs
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Wi-Fi
    • Central Heating
    • DVD Player
    • Waterfront
    • Satellite TV
    • Ocean Views
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Stockton Springs, Mid Coast Maine 04981
    4 of 5 bubbles Reviewed 3 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, but other...
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    1 / 8
    Penobscot
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Parking
    • Waterfront
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Penobscot is a tiny, unspoiled town with a little market (great breakfast sandwiches and coffee to go, ready by 6:30 am!) and a traditional Maine "clam shack" (whole take out lobsters cooked to order, $6 last summer), an ideal location to explore the Blue Hill peninsula, home to many excellent... View all property information
    Location Information
    Penobscot, DownEast and Acadia Maine 04476
    1 / 8
    Orland
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
    • Parking
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-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,... View all property information
    Location Information
    Orland, DownEast and Acadia Maine 044
    1 / 8
    5 of 5 bubbles (1) Excellent
    Sandy Point
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Internet Access
    • Parking
    • Waterfront
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    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.... View all property information
    Location Information
    Sandy Point, Mid Coast Maine 04416
    5 of 5 bubbles 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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    1 / 30
    5 of 5 bubbles (3) Excellent
    Swanville
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Sauna
    • Satellite TV
    • Internet Access
    • DVD Player
    • Mountain Views
    • Central Heating
    • Balcony
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Swanville, Mid Coast Maine 04915
    5 of 5 bubbles Reviewed 28 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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    1 / 15
    5 of 5 bubbles (27) Excellent
    Frankfort
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Satellite TV
    • Washer
    • DVD Player
    • Grill
    • Mountain Views
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    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 enjoyable week at the lake including all bed... View all property information
    Location Information
    Frankfort, Mid Coast Maine 04438
    1 / 13
    5 of 5 bubbles (9) Excellent
    Swanville
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Balcony
    • Waterfront
    • Grill
    • Satellite TV
    • Washer
    • Porch
    • Central Heating
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Swanville, Mid Coast Maine 04915
    1 / 14
    5 of 5 bubbles (8) Excellent
    Swanville
    1 Bedroom, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Internet Access
    • Washer
    • Private Garden
    • Satellite TV
    • Grill
    • Patio
    • Waterfront
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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,... View all property information
    Location Information
    Swanville, Mid Coast Maine 04915
    5 of 5 bubbles Reviewed 8 October 2016
    We loved our stay on Swan Lake, this is our second visit and we just loved Dennis and Kim's place. You will not be disappointed - the photos cannot do this place justice...
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    1 / 10
    4.5 of 5 bubbles (2) Very good
    Orrington
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Internet Access
    • DVD Player
    • Grill
    • Washer
    • Patio
    • Air Conditioning
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    $770 per week- 2br - 900ft2 - Awesome Lake Vacation Rental (Near Bangor Maine) 947 Brewer Lake Road, Orrington, Maine Rest and relaxation are a sure bet at this lakefront retreat close to Acadia National Park. Located on serene Brewer Lake just minutes from Bangor, Maine enjoy lakefront... View all property information
    Location Information
    Orrington, Maine 04474
    1 / 40
    5 of 5 bubbles (1) Excellent
    Stockton Springs
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Central Heating
    • Internet Access
    • Mountain Views
    • DVD Player
    • Grill
    • Washer
    • Satellite TV
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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.... View all property information
    Location Information
    Stockton Springs, Mid Coast Maine 04981
    1 / 11
    3 of 5 bubbles (3) Average
    Swanville
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Mountain Views
    • DVD Player
    • Satellite TV
    • Waterfront
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy the Eagles, Loons, Gorgeous Pink and Purple Sunrises and Sunset skies from your Deck, Adirondack, Dock or Float, canoe or kayak on Beautiful, Clean, Clear Swan Lake. It is only fifteen minutes from the Maine Coast on Penobscot Bay/Searsport, Belfast area; 45 minutes from Camden. It is... View all property information
    Location Information
    Swanville, Mid Coast Maine 04915
    3 of 5 bubbles 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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    1 / 19
    Orland
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Outdoor Dining Area
    • Grill
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Perched above the banks of the Penobscot River just minutes to Castine or Bucksport, Riverhouse in Orland offers guests a cozy retreat. Beautifully renovated, this 2 bedroom 1 bathroom home has all the feelings of home. Guests will receive a feeling of peace and tranquility before even stepping a... View all property information
    Location Information
    Orland, DownEast and Acadia Maine 04472