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Orland Holiday Homes

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    Don't let other travellers get your favourite Orland area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 18 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
    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
    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
    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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    Orland, DownEast and Acadia Maine 04472
    Holiday Rental House - 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
    Holiday Rental House - 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
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    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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    Orland, DownEast and Acadia Maine 04472
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    The following rentals are within 15 kilometres of Orland.
    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 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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    Penobscot
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid 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...
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    Penobscot, DownEast and Acadia Maine 04476
    Holiday Rental House - 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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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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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    Amenities & Details
    • Central Heating
    • Wi-Fi
    • Mountain Views
    • DVD Player
    • Patio
    • Washer
    • Cable/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
    '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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    Amenities & Details
    • Parking
    • Waterfront
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 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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    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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    Amenities & Details
    • Washer
    • DVD Player
    • Ocean Views
    • Waterfront
    • Central Heating
    • Wi-Fi
    • Mountain Views
    • Cable/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
    '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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    • DVD Player
    • Wi-Fi
    • Housekeeping Included
    • Mountain Views
    • Air Conditioning
    • Washer
    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 September 2018
    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 28 August 2018
    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
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 26
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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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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