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.

Holiday Rentals in Bailey Island

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
    ₹ 12,694 Average
    |||
    |||
    ₹ 0₹ 68,000+
    Suitability
    More filters
    Bailey Island is popular with travellers just like you. Don’t let them get your perfect place first—book today!
    All 15 Rentals in Bailey Island
    Sort by:
    Default
    7 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walk into a renters dream when you enter this 2 bedroom, 2.5 bathroom house located on quiet West Shore Road. Enjoy a large wraparound deck on the living level and two balcony decks on the second level you will never miss a scenic sunset on Harpswell sound. Enjoy the convenience of walking to the...
    View all property information
    Location Information
    Bailey Island, Maine 04003
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely cottage is situated on a dead end road, perched above Little Harbor. Enjoy spectacular Easterly views.There is a great wrap around porch to enjoy all the beauty the outside has to offer. Be sure to bring your camera to capture the glorious sunrises so you can savor them throughout the...
    View all property information
    Location Information
    Bailey Island, Maine 04003
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Look no further! This recently renovated cape is perched high on the island offering panoramic, open ocean views, complete with breathtaking sunrises & sunsets; as well as the large lawn to enjoy the view and sweet salt air. This property can accommodate up to 8 guests and is conveniently located...
    View all property information
    Location Information
    Bailey Island, Maine 04003
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cute two story cottage has a great location overlooking Harpswell Sound. Take in the Maine cottage feel when you walk into this clean, well-kept cottage. A newly renovated kitchen allows you to cook gourmet meals at your vacation home and enjoy them on your glassed-in porch which has...
    View all property information
    Location Information
    Bailey Island, Maine 04003
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Gagnier's cottage is an adorable ranch which sits on top of a hill, and provides spectacular sunset views from the wrap around deck, or inside on the main level. There is a right of way to the rocky oceanfront directly across the street. Enjoy taking walks on this quiet road to Cook's Lobster &...
    View all property information
    Location Information
    Bailey Island, Maine 04003
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Wi-Fi
    • DVD Player
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 bedroom, 2 bathroom, year round home has a large deck and steps to the rocky shore! From the deck watch the lobster boats get their daily catch and enjoy spectacular sunset views over Harpswell Sound. There are steps that lead down to the rocky shore. This home is well maintained and...
    View all property information
    Location Information
    Bailey Island, Maine 04003
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for the perfect couples getaway? Look no further! This quaint cottage located in the quiet West Shore neighborhood of Bailey Island offers breathtaking sunsets over Harpswell Sound. Although a smaller cottage, it is the perfect size for two people. Enjoy sitting in the sunroom or outside on...
    View all property information
    Location Information
    Bailey Island, Maine 04003
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Save time - get the best Bailey Island rentals sent straight to your email!
    Get the List
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The simplicity of this quaint, coastal, 2 bedroom cottage is what affords it such charm! This vacation cottage brings you gorgeous sunset views out to the ocean from both front and rear decks. Picnic tables on each deck allow wonderful spots for outdoor dining. Kitchen has all the necessities for...
    View all property information
    Location Information
    Bailey Island, Maine 04003
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Steamboat Landing is a charming two bedroom cottage sitting directly on Mackerel Cove. Wake up to the Sea Salt air. Enjoy a meal from the large deck that sits right over the water while watching the lobster boats return from getting their daily catch. Bring a boat and utilize the mooring available...
    View all property information
    Location Information
    Bailey Island, Maine 04003
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cute little cottage is located almost at the end of the Island. A Beautiful deck with views facing south west, enjoy the incredible sunsets! Watch as the lobstermen come and go from the cove. There is rocky shore front access a short walk from the cottage. A full kitchen with new appliances...
    View all property information
    Location Information
    Bailey Island, Maine 04003
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a rustic Maine cottage? Look no further! This three bedroom cottage has all the charm you are looking for while still giving you modern day amenities. Enjoy great views of scenic Mackerel Cove from the covered porch. This turn-of-the-century cottage keeps its charm with wood-paneled...
    View all property information
    Location Information
    Bailey Island, Maine 04003
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This sweet single story cottage sits on Tip-Top Hillside, with views into Mackerel Cove and beyond. Enjoy sitting on the spacious deck and watching the lobstermen go in and out of the cove or walk down the wooded path to the shared dock and space near water's edge. With handicap accessibility this...
    View all property information
    Location Information
    Bailey Island, Maine 04003
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    List your property
    Owner log in