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Winterport Vacation Rentals

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    Don't let other travelers get your favorite Winterport area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 17 Rentals in Winterport
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    The following rentals are within 10 miles of Winterport.
    The Round House on 53 Private Wooded Acres 10 minutes from Belfast1 / 30
    (4)Excellent
    Swanville
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Private Bayside Retreat On Penobscot Bay: Ask About My Short-Week Summer Special1 / 25
    (3)Excellent
    Bucksport
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Tranquility on Penobscot Bay Retreat:  Ask Me About My Short-Week Summer Special1 / 42
    (2)Excellent
    Stockton Springs
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    The Riverhouse1 / 35
    (7)Excellent
    Orland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Secure Parking
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 17, 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 November 13, 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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    Location Information
    Orland, DownEast and Acadia Maine 04472
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Seacroft1 / 19
    (16)Very good
    Stockton Springs
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • DVD Player
    • Parking
    • Cable/satellite TV
    • Patio
    • Grill
    • Internet Access
    • Shared Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 7, 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 October 3, 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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    Location Information
    Stockton Springs, Mid Coast Maine 04981
    Cabin - 1 Bedroom, 1 Bathroom, Sleeps 2
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    SWAN LAKE COTTAGE,  PRIVATE BEACH, DOCK1 / 16
    (14)Excellent
    Swanville
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Washer
    • Private Yard
    • Cable/satellite TV
    • Grill
    • Patio
    • Waterfront
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 days ago
    The cabin was so quaint and very clean. Dennis was very friendly. It was so relaxing. My husband enjoyed fishing off the dock. My son pitched a tent in the backyard. Not too far...
    Reviewed August 13, 2018
    This was a fantastic vacation spot. The cottage was exceptionally clean and inviting, with an absolutely gorgeous view of the lake. The beach area is easily accessed, with a...
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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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    Location Information
    Swanville, Mid Coast Maine 04915
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    Orland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    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. Lovingly decorated with a gentle country charm. Camp Linger has charming decor with beadboard, wood floors...
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    Location Information
    Orland, DownEast and Acadia Maine 04472
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Orland
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • Parking
    • Central Heating
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A charming cottage set amongst evergreen trees just 100 feet from the shore. Enjoy cooking fresh Maine lobster and blueberry pie in a full kitchen, or grill in the open air on a gas grill while experiencing the sun setting over the pond. The cottage dining area with cathedral ceiling and lighted...
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    Location Information
    Orland, DownEast and Acadia Maine 04472
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Sandy Point Home w/Wraparound Deck - Walk to Beach1 / 26
    (1)Excellent
    Sandy Point
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Central Heating
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 12, 2017
    This property delivers all that its description boasts! First, the design is comfortable and classy, as the photos show. Our multi-generational family (including friends) have...
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    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...
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    Location Information
    Sandy Point, Mid Coast Maine 04972
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Private Sandy Beach, Sleeps 24+ large family's, Retreats and Weddings   5 star1 / 59
    (14)Excellent
    Sandy Point
    7 Bedrooms, 3 Bathrooms, Sleeps 26 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Housekeeping Included
    • Mountain Views
    • Air Conditioning
    • Washer
    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    This is the 2nd year we have held our staff party at this amazing house. Its huge with enough room for 3 or 4 families. We use it for our staff as an end of season...
    Reviewed 4 weeks ago
    Where do I start? What a fun, eclectic house with the best dining room table our family has all been able to sit, at one time. The views, the deck, the beach, the sealsmade for...
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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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    Location Information
    Sandy Point, Mid Coast Maine 04981
    Rental Home - 7 Bedrooms, 3 Bathrooms, Sleeps 26
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    Lakeside Cabin Near Belfast Bay w/ Kayaks & Canoe1 / 21
    (5)Average
    Swanville
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Mountain Views
    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 23, 2018
    Becky and Don were very welcoming and because the waterfront at the cabin is not suitable for swimming (but a very pretty setting), they make their waterfront next door...
    Reviewed January 14, 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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    Location Information
    Swanville, Mid Coast Maine 04915
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 5
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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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    Location Information
    Bucksport, DownEast and Acadia Maine 04416
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Orland
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lazy Lane is a beautiful upscale 3 bedroom, 2 bathroom home on well landscaped grounds in Bucksport. Enjoy all the comforts of home like WiFi internet, Satellite TV, washer & dryer and a fully equipped kitchen. Master bedroom with attached full bathroom is located on the first floor off the...
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    Location Information
    Orland, DownEast and Acadia Maine 04416
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Orland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are happy to accept reservations with a 3 night minimum, please contact us directly for pricing. Red Cottage on Toddy Pond is a charming, newly updated, cozy 1 bedroom, 1 bathroom cottage on a shared property in Orland. The cottage features a fully equipped kitchen with all dishes and...
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    Location Information
    Orland, DownEast and Acadia Maine 04472
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Orland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are happy to accept reservations with a 3 night minimum, please contact us directly for pricing. This charming, newly updated, 1 bedroom, 1 bathroom cottage known as Loon Cottage is located on a shared property down a quiet, private dirt road on the waters of Toddy Pond. Enjoy watching the sun...
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    Location Information
    Orland, DownEast and Acadia Maine 04472
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Stockton Springs
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Waterfront
    • Washer
    • Grill
    • Central Heating
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cappy’s Retreat is a 3 bedroom plus loft, 2 bathroom home located in Stockton Springs on the Penobscot River. This recently remodeled home features new quartz kitchen counters, new stainless steel appliances, new floors throughout and new deck. Enjoy all the amenities of home while enjoying 2.9...
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    Location Information
    Stockton Springs, Mid Coast Maine 04981
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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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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    Location Information
    Orland, DownEast and Acadia Maine 04431
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Bangor Intl Airport
    12.4 miles from Winterport
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