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  • Wake to Sunrise on the Ocean

    Bailey Island, ME

    Enjoy all three seasons, Spring Summer and the quiet of Fall. Central heat and fireplace will keep you toasty in this traditional 1891shingle-style cottage sitting on a bluff with ocean views from... ...more

    Beds: 4 Baths: 2 Property type: Cottage (18) Wonderful
    $392 / Nightly
  • Authentic maine cottage with direct water frontage

    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 access from the back yard to the... ...more

    Beds: 3 Baths: 1 Property type: Cottage (9) Very Good
    $197 / Nightly
  • Charming rustic cottage on the ocean, with semi-private beach

    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 east and to the west. A covered,... ...more

    Beds: 5 Baths: 2 Property type: Cottage (21) Wonderful
    $172 / Nightly
  • Great Sunsets, oceanfront cottage sleeps 6

    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 Bailey Island. Indeed it is an island,... ...more

    Beds: 2 Baths: 1 Property type: Cottage (4) Exceptional
    $248 / Nightly
  • 1890 Summer Cottage on an Ocean Bluff

    Bailey Island, ME

    This Maine summer cottage on Bailey Island sits on a high bluff overlooking the ocean. First bought by great, great grandparents on their honeymoon trip, it has been in the family for over 125... ...more

    Beds: 5 Baths: 2 Property type: Cottage (10) Exceptional
    $339 / Nightly
  • Enjoy Amazing Views from our Well Appointed and Welcoming Home

    Bailey Island, ME

    Available for weekly rentals during the summer season and two night and more stays in the off seasons.The house is also available for retreats and special events. The well appointed Captain... ...more

    Beds: 4 Baths: 5 Property type: House (24)
    $985 / Nightly
  • Wonderful family friendly home , 10% discount on posted rental rates thru 2018

    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 also offers opportunities for... ...more

    Beds: 4 Baths: 2 Property type: House (35)
    $241 / Nightly
  • Charming 2 bedroom cottage sitting directly on picturesque Mackerel Cove

    Bailey Island, ME

    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... ...more

    Beds: 2 Baths: 2 Property type: Cottage (1) Exceptional
    Select Dates for Price
  • Charming, Coastal, Authentic

    Bailey Island, ME

    The May Cottage is a beloved place by our family. We have done some remodeling over the years while trying to keep the original feel of the cottage intact. The rooms are small and comfortable,... ...more

    Beds: 0 Baths: 1 Property type: Cottage (4) Exceptional
    $151 / Nightly
  • Sunset Cottage located on very desirable quiet West Shore Road!

    Bailey Island, ME

    The Gagnier's cottage is an adorable raised ranch with a walk out basement, which sits on top of a hill, and provides spectacular sunset views from the wrap around deck, or inside on the main... ...more

    Beds: 2 Baths: 2 Property type: House (5) Wonderful
    Select Dates for Price
  • Comfortable Bailey Island home with fabulous sunsets, and large waterside deck.

    Bailey Island, ME

    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 the... ...more

    Beds: 3 Baths: 2 Property type: House (0)
    Select Dates for Price
  • Beautiful log cabin steps from the beach! Ocean Front!

    Bailey Island, ME

    Authentic log cabin nestled in a gorgeous spot surrounded by trees and ocean view. Private sandy Beach. Quiet and secluded, you will love sitting on the enormous (560 square ft) deck just to relax... ...more

    Beds: 2 Baths: 1 Property type: Cabin (9) Wonderful
    $239 / Nightly
  • PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

    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 room. The property is well off the... ...more

    Beds: 5 Baths: 4 Property type: Cottage (38)
    Select Dates for Price
  • Immaculate home! Wrap around porch, balconies, amazing sunset and waterviews!

    Bailey Island, ME

    Walk into a renters dream when you enter this two bedroom, 2 1/2 bathroom house located on quiet west shore road. With a wraparound deck on one level and two balcony decks on the second level you... ...more

    Beds: 2 Baths: 3 Property type: House (0)
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  • Quintessential Maine Cottage Overlooking the World Famous Cribstone Bridge!

    Bailey Island, ME

    Crossing over the Cribstone bridge to Bailey Island, look right - that's Wentworth Cottage! The cottage is filled with character and memories. Freshly renovated this cottage is the perfect central... ...more

    Beds: 2 Baths: 1 Property type: Cottage (2) Exceptional
    Select Dates for Price
  • The Captain York House

    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 families, large groups and family... ...more

    Beds: 7 Baths: 7 Property type: House (5) Exceptional
    $482 / Nightly
  • Seaside Cottage on Bailey Island with Views of Picturesque Mackerel Cove

    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 Cove and Mackerel Cove beach. Settled... ...more

    Beds: 3 Baths: 2 Property type: Cottage (5) Exceptional
    $473 / Nightly
  • Classic Maine Cottage w/ expansive easterly waterviews, located near Cedar Beach

    Bailey Island, ME

    Bring the kids with you to this family-friendly cottage located on beautiful Bailey Island. Enjoy easterly views while you picnic on the upstairs deck with comfortable outdoor furniture. Let the... ...more

    Beds: 2 Baths: 1 Property type: Cottage (2) Excellent
    Select Dates for Price
  • New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

    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, heated and cooled by solar and... ...more

    Beds: 3 Baths: 2 Property type: House (54)
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  • Sweet Bailey Island Cottage w/a Great Ocean View Deck & Steps to the Shore.

    Bailey Island, ME

    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.... ...more

    Beds: 1 Baths: 1 Property type: Cottage (2) Very Good
    Select Dates for Price
Search result 1 to 20 Of 28