We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Orland Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    C$273 Average
    |||
    |||
    C$0C$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Orland area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 19 Rentals in Orland
    Sort by:
    Default
    Orland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    The Riverhouse1 / 35
    (7)Excellent
    Orland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Orland
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Orland
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Orland, DownEast and Acadia Maine 04431
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    Orland
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Grill
    • Internet Access
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pack up the family and head to dog-friendly Ladybug Hollow, which boasts peekaboo views of Upper Patten Pond. The detached bedroom apartment is perfect for those wanting privacy. Despite proximity to the main thoroughfare, loons can be heard at night, and you might wake up to a flock of wild...
    View all property information
    Location Information
    Orland, DownEast and Acadia Maine 04472
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    The following rentals are within 15 kilometres of Orland.
    Penobscot
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    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...
    View all property information
    Location Information
    Penobscot, DownEast and Acadia Maine 04476
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    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
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Housekeeping Included
    • Mountain Views
    • Air Conditioning
    • Washer
    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 13, 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 August 27, 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...
    See all reviews
    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...
    View all property information
    Location Information
    Sandy Point, Mid Coast Maine 04981
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 26
    Make Enquiry
    Seacroft1 / 19
    (16)Very good
    Stockton Springs
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Parking
    • Cable/satellite TV
    • Patio
    • Grill
    • Internet Access
    • Shared Garden
    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...
    See all reviews
    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
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    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
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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 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...
    See all reviews
    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)...
    View all property information
    Location Information
    Bucksport, DownEast and Acadia Maine 04981
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Maine. Lovely Cottage on Penobscot Bay1 / 20
    (12)Very good
    Penobscot
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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...
    See all reviews
    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
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Save time - get the best Orland rentals sent straight to your email!
    Get the List
    Bucksport
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    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,...
    View all property information
    Location Information
    Bucksport, DownEast and Acadia Maine 04416
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    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
    Check in Check out
    Show Prices
    Payment Protection
    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 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...
    See all reviews
    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)...
    View all property information
    Location Information
    Stockton Springs, Mid Coast Maine 04981
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Sandy Point Home w/Wraparound Deck - Walk to Beach1 / 26
    (1)Excellent
    Sandy Point
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    See all reviews
    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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
    Make Enquiry
    Stockton Springs
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    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...
    View all property information
    Location Information
    Stockton Springs, Mid Coast Maine 04981
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Bucksport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Central Heating
    • Terrace
    • Balcony
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that there is another vacation rental unit on the premises, with some shared outdoor amenities ** Discover the beauty of coastal Maine while staying in this charming vacation rental home in Bucksport. This 900-square-foot apartment includes contemporary furnishings, 1 queen...
    View all property information
    Location Information
    Bucksport, DownEast and Acadia Maine 04416
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Dedham
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Dedham, Maine 04429
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Dedham
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Dedham, Maine 04429
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Penobscot
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Waterfront
    • Central Heating
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A one-of-a-kind escape awaits at 'Lilac Cottage,' a 3-bedroom, 2-bathroom vacation rental house in Penobscot. This historical home was built in 1790 using trees and stones found on the 5.3-acre property and is located near American Revolution battle sites. Though the home retains much of its...
    View all property information
    Location Information
    Penobscot, DownEast and Acadia Maine 04476
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Make Enquiry
    Bucksport
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Cable/satellite TV
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **Please note that there is another vacation rental unit on the premises, with some shared outdoor amenities** Look forward to a magical getaway in coastal Maine at this Bucksport vacation rental home. You'll fall in love with the classic Victorian-style house with its enchanting vintage...
    View all property information
    Location Information
    Bucksport, DownEast and Acadia Maine 04416
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    List your property
    Owner log in