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Orland Vacation Rentals

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    Don't let other travellers get your favourite Orland area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 18 Rentals in Orland
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    Orland
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Orland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    The Riverhouse1 / 35
    (7)Excellent
    Orland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    The following rentals are within 15 kilometres of Orland.
    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
    • Satellite TV
    • DVD Player
    • Patio
    • Internet Access
    • Grill
    • Parking
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 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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    Sandy Point, Mid Coast Maine 04972
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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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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    Dedham
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Washer
    • Grill
    • 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 good....
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    Dedham, Maine 04429
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Dedham
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • 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 Lake,...
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    Dedham, Maine 04429
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    Tranquility on Penobscot Bay Retreat:  $200/nt Last Minute Deal from 9/25 - 10/11 / 42
    (2)Excellent
    Stockton Springs
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Location Information
    Stockton Springs, Mid Coast Maine 04981
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    Location Information
    Sandy Point, Mid Coast Maine 04416
    Holiday Rental House - 4 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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    Amenities & Details
    • 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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    Location Information
    Stockton Springs, Mid Coast Maine 04981
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Private Sandy Beach, Sleeps 24+ large family's, Retreats and Weddings   5 star1 / 59
    (10)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 3 weeks ago
    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...
    Reviewed 3 weeks ago
    We had a nice week in the house with all the family (8 adults and 9 children). Plenty of room for everyone and had everything we needed for a fantastic stay. The time down on...
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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
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 26
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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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    Bayside Retreat: Panoramic Views of Penobscot Bay1 / 26
    (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
    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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    Penobscot
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    Penobscot
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    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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    Location Information
    Stockton Springs, Mid Coast Maine 04981
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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