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Bailey Island: Vacation Rental By Owner

Search result 1 to 15 Of 15
  • Property-1 Image 1
    House $525 / Nightly
    • 3Bed
    • 4Baths
    Bailey Island, Maine

    Enjoy this picturesque Bailey Island setting on 2.06 acres and 199’ frontage on Maine’s rocky coast. Completely renovated in 2006-07 this Shingle Style oceanfront... ...more

  • Property-2 Image 1
    House $495 / Nightly
    • 7Bed
    • 6Baths
    Bailey Island, Maine

    The historic Captain York House has been on Bailey Island for more than 100 years. It has expanded into a 7 bedroom, 6.5 bathroom house that can accommodate... ...more

  • Property-3 Image 1
    Cottage Select Dates for Price
    • 2Bed
    • 1Baths
    • (4) Exceptional
    Bailey Island, ME

    Bailey Island waterfront, bold surf, private, updated and location, location, location! This cozy, oceanfront cottage on Bailey Island oversees what was once... ...more

  • Property-4 Image 1
    Cottage $473 / Nightly
    • 3Bed
    • 2Baths
    • (6) Excellent
    Bailey Island, ME

    Having undergone a foundation-up renovation completed in August 2011, Homeport offers a modern design, allowing you to enjoy the magnificent views of Mackerel... ...more

  • Property-5 Image 1
    Cottage $248 / Nightly
    • 2Bed
    • 1Baths
    • (4) Exceptional
    Bailey Island, ME

    Sunset-facing Bayfront directly on Merriconeag Sound, SEABREEZE was built it in 2002. It replicates many of the old (1880's) fishing cottages to be found on... ...more

  • Property-6 Image 1
    House $108 / Nightly
    • 1Bed
    • 1Baths
    • (12) Exceptional
    Bailey Island, ME

    New for 2018! One bedroom home on Bailey Island with easterly ocean views, view of Little Harbor, and limited view of Mackerel Cove. Access to Little Harbor is... ...more

  • Property-7 Image 1
    House Select Dates for Price
    • 4Bed
    • 2Baths
    • (35)
    Bailey Island, ME

    The Johnson Homestead is located near the south end of Bailey Island, Maine. It can be the ideal quiet spot for those guests looking for rest and relaxation, yet... ...more

  • Property-8 Image 1
    Cottage $135 / Nightly
    • 5Bed
    • 2Baths
    • (21) Wonderful
    Bailey Island, ME

    The Nezinscott is located on the southerly portion of picturesque Bailey Island, Maine. The property borders and overlooks Little Harbor, with ocean views to the... ...more

  • Property-9 Image 1
    House $517 / Nightly
    • 5Bed
    • 5Baths
    • (6) Exceptional
    Bailey Island, ME

    Summer Salt is an excellent waterfront property located on Bailey Island. The property offers magnificent open ocean views of Casco Bay and views of Ragged... ...more

  • Property-10 Image 1
    Cottage $340 / Nightly
    • 2Bed
    • 1Baths
    • (41) Wonderful
    Bailey Island, ME

    Ocean Breeze Cottage on Bailey Island is now available for your seaside vacation, no matter the season. This well-insulated cottage, heated by geothermal... ...more

  • Property-11 Image 1
    House $489 / Nightly
    • 4Bed
    • 2Baths
    • (15) Exceptional
    Bailey Island, ME

    Be Our Guest...Oceanfront Home on Bailey Island. This oceanfront home offers stunning sunrises & colorful sunsets and sleeps up to 8. There are water views of the... ...more

  • Property-12 Image 1
    Cottage Select Dates for Price
    • 3Bed
    • 1Baths
    • (9) Very Good
    Bailey Island, ME

    This turn of the century cottage has been lovingly preserved and updated tastefully by our family for 4 generations. Located on Merriconeag Sound, it has easy... ...more

  • Property-13 Image 1
    House $528 / Nightly
    • 3Bed
    • 2Baths
    • (54)
    Bailey Island, ME

    Newly Constructed Friendly Cottage on Oceanside, Bailey Island is now available for your seaside vacation, no matter the season. This well-insulated cottage,... ...more

  • Property-14 Image 1
    Cottage $997 / Nightly
    • 5Bed
    • 4Baths
    • (38)
    Bailey Island, ME

    JAQUISH LANE Perched on a stretch of rocky Maine coast, Jaquish Lane is a fully renovated oceanfront compound with stunning views of the sea from nearly every... ...more

  • Property-15 Image 1
    House $482 / Nightly
    • 7Bed
    • 7Baths
    • (5) Exceptional
    Bailey Island, ME

    The historic Captain York House has been on Bailey Island for more than 100 years. It has expanded into a 7 bedroom, 7 bathroom house that can accommodate... ...more

Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Bailey Island. Many accommodations in Bailey Island provide "Beach", there are 28, or there are 28 of Vacation Rentals in Bailey Island with a "Fishing", there are also 27 with "Swimming", which is another great reason to visit Bailey Island.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Bailey Island. The most expensive month of the next 12 months is in February, where prices hit an average of $0 a night. In December, prices will hit an average low of $248 per night.