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Vacation Rentals in Gloucester, MA

(1 - 15 of 63)
  1. This oceanfront year round home was recently constructed to maximize spectacular ocean views and sunsets. Enjoy the views of the water ou...
    Marketplace User ·6 days ago on Flipkey
  2. Welcome, cher ami ("dear friend"), to this gleaming and immaculate, 2nd floor vacation rental. Cher Ami is available as a summer rental a...
    Marketplace User ·1 week ago on Flipkey
  3. This charming, romantic one beds townhouse is located in a peaceful, seaside neighborhood on the desirable Rocky Neck in Gloucester Harbo...
    Marketplace User ·1 week ago on Flipkey
  4. Captain's Watch House is a Gloucester vacation rental located just a lane away from iconic Stacey Boulevard. This 3 beds/1.5 bathrooms ge...
    Marketplace User ·1 week ago on Flipkey
  5. Just ten yards from the white sands and lively surf of Long Beach, this vacation rental condominium sleeps eight in central a/c comfort a...
    Marketplace User ·1 week ago on Flipkey
  6. This delightful 3 beds, 1.5 bathrooms Queen Anne-style vacation rental home is bright and cheery and just waiting for you! Enter the hous...
    Marketplace User ·1 week ago on Flipkey
  7. A delightful vacation home situated in Gloucester's charming Bay View neighborhood, Annie's Place radiates an aura of sun and warmth. Onl...
    Marketplace User ·1 week ago on Flipkey
  8. Enjoy the beauty of Cape Ann at this romantic cottage. Direct ocean front in America's oldest seaport. Immaculate 2 beds cottage brings b...
    Marketplace User ·2 weeks ago on Flipkey
  9. Enjoy this comfortable newly up-to-date 3 beds, one bathrooms vacation home conveniently located a block away from Gloucester's scenic ou...
    Marketplace User ·2 weeks ago on Flipkey
  10. This large, comfortable family-oriented vacation home is just steps from the white sands of Long Beach--a perfect summer location! Built ...
    Marketplace User ·2 weeks ago on Flipkey
  11. This Friday to Friday vacation rental is right at Good Harbor Beach. Step out the door, walk over the Good Harbor Beach footbridge and yo...
    Marketplace User ·2 weeks ago on Flipkey
  12. Enjoy the views of the sparkling waters of the Annisquam River and Ipswich Bay beyond as well as Wingarsheek Beach and the Annisqaum Yach...
    Marketplace User ·2 weeks ago on Flipkey
  13. This sweet two beds vacation rental apartment--quite the pied a terre-- has views of Ipswich Bay from its 2nd floor vantage point. It has...
    Marketplace User ·2 weeks ago on Flipkey
  14. Location, location, location! Waterviews & a quick walk to Good Harbor Beach. This four beds/2.5 bathrooms vacation home is large and com...
    Marketplace User ·2 weeks ago on Flipkey
  15. Relax and take in great views of Gloucester's beautiful Good Harbor Beach, with Thatcher Island beyond, from this bright and delightfully...
    Marketplace User ·2 weeks ago on Flipkey

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