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Orland Vacation Rentals

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    All 21 Rentals in Orland
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    The Riverhouse1 / 35
    (7)Excellent
    Orland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Orland
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Orland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Orland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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...
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    Orland, DownEast and Acadia Maine 04472
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Orland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Red Cottage on Toddy Pond is a charming, rustic, cozy 1 bedroom, 1 bathroom cottage on a shared property in Orland. The cottage features a fully equipped kitchen with all dishes and cookware. Satellite TV and WiFi are equipped to keep you occupied on a rainy day. Enjoy watching the sunset over...
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    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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    • Grill
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming, rustic 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 set behind the trees and over the waters of the pond while sitting on the deck. Inside you can enjoy a...
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    Orland, DownEast and Acadia Maine 04472
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Orland, DownEast and Acadia Maine 04416
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Orland
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • 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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    The following rentals are within 10 miles of Orland.
    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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    • Washer
    • DVD Player
    • Ocean Views
    • Waterfront
    • Central Heating
    • Wi-Fi
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 22, 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
    'BIG SUMMER SALE': Check out these discounted time slots for a budget vacation - contact me for more information: (1) 8/8 - 8/11: 3 nights at $600 ($650 savings) (2) 9/7 - 9/10: 3 nights at $975 (3) 9/17 - 9/21: 4 nights at $900 ($300 savings) (4) 9/25 - 9/29: 4 nights at $990 ($300 savings)...
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    Location Information
    Bucksport, DownEast and Acadia Maine 04981
    Rental Home - 3 Bedrooms, 3 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
    • 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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    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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    • Central Heating
    • Wi-Fi
    • Mountain Views
    • DVD Player
    • Patio
    • Washer
    • Cable/satellite TV
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 17, 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
    'BIG SUMMER SALE': Check out these discounted time slots for a budget vacation - contact me for more information: (1) 8/8 - 8/11: 3 nights at $600 ($650 savings) (2) 9/7 - 9/10: 3 nights at $975 (3) 9/17 - 9/21: 4 nights at $900 ($300 savings) (4) 9/25 - 9/29: 4 nights at $990 ($300 savings)...
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    Location Information
    Stockton Springs, Mid Coast Maine 04981
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    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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    Maine. Lovely Cottage on Penobscot Bay1 / 40
    (12)Very good
    Penobscot
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Waterfront
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 12, 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 June 4, 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
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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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
    • Cable/satellite TV
    • Internet Access
    • Parking
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 9, 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 farmhouse and barn with 3 - car garage rests on 38+ acres of shore frontage with lush field, pasture and woodland. Beautifully landscaped with gardens, patio, decking and pool. Watch deer and other birds and wildlife, or walk the extensive acreage and shoreline....
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    Location Information
    Sandy Point, Mid Coast Maine 04416
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Private Sandy Beach, Sleeps 24+ large family's, Retreats and Weddings   5 star1 / 59
    (11)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 April 14, 2018
    Me and some friends and co workers who were all in the region decided together. Found this place by doing a search for lodges close to route 1 Maine, it's literally maybe 2...
    Reviewed September 26, 2017
    It was the best place for a big group like us that 's 17 adults,2 kids and a havanese dog. We stayed from Sep. 1 -4, 2017. We love the retreat house,the long hardwood dining...
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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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    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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    Dedham
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Washer
    • Grill
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Dedham, Maine 04429
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    Location Information
    Penobscot, DownEast and Acadia Maine 04476
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Penobscot
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • Ocean Views
    • Central Heating
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Penobscot, DownEast and Acadia Maine 04476
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Dedham
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Parking
    • Patio
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy stunning views of Phillips Lake at this two-bedroom Dedham cottage, a wonderful lakefront home with two decks, a screened-in porch, a private dock, and four kayaks to help you explore this lovely region of Maine! This tranquil wooded property is located on the northern banks of Phillips...
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    Location Information
    Dedham, Maine 04429
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Penobscot
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Grill
    • Waterfront
    • Central Heating
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Follow your wanderlust to the colorful coast of the Cape! This 18th-century waterfront vacation rental house will serve as the foundation for your relaxing Penobscot trip. Well appointed with 3-bedrooms, 2-bathrooms, this home easily sleeps 7 guests and features a prime location on the shores of...
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    Location Information
    Penobscot, DownEast and Acadia Maine 04476
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Orland Flight and Weather Info
    Airports nearby (1)
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    BGR
    Bangor Intl Airport
    16.9 miles from Orland
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