Gloucester Rentals Make Great Destinations

When you are looking for a great way to spend time on the northern Massachusetts shore, Gloucester – Annisquam rentals are excellent choices. Rentals in Gloucester, MA offer the convenience of being near downtown Gloucester while still remaining just outside the city.

Enjoy Quiet Relaxation on Wingaersheek Beach, North Shore


If you are seeking a quiet Gloucester rental, then Wingaersheek Beach along the Annisquam River is the perfect destination for your vacation. This Gloucester beach has white sand and great rocks that form tide pools for the kids to play in. The Annisquam neighborhood is mostly residential and offers few commercial businesses. The area does offer a marina, yacht club, restaurant, and the famed Annisquam lighthouse. The lighthouse has stood since 1801 and the beach on which it sits is known as Lighthouse Beach. There are many Annisquam rentals near Gloucester, MA that offer beautiful views of the historic lighthouse.

A Gloucester Rental Offers a Great Way to See a Beautiful City


Gloucester, Massachusetts is a wonderful city that offers many places for travelers to explore. Take in the beautiful city hall building, which is only one example of the city's famous and significant architecture. Gloucester – Annisquam rentals provide guests with easy access to such attractions as the Man at the Wheel statue as well as the many art and sculpture museums. The city has been mentioned in many famed films and books, and a brief tour of the city helps show visitors exactly why. A Gloucester rental makes a perfect accommodation for travelers looking to see the historic area and guests lucky enough to come during the St. Peter's Festival will find that the city is filled with culture.

Rentals in Gloucester, MA Also Offer Outdoor Activity and Beautiful Surroundings


Gloucester – Annisquam rentals give guests the chance to explore the Massachusetts Bay as well as the Atlantic Ocean. The location is ideal for boaters and offers many options for fishing, swimming, and sailing.

When you decide to spend your vacation in a Gloucester rental, you will find yourself in a beautiful accommodation that features full furnishings and many amenities. Rentals in Gloucester, MA are available to suit any size family or group and offer wonderful accommodations for travelers looking to relax and enjoy the beauty of Eastern Massachusetts. Search today!

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Gloucester - Annisquam: Houses, Cottages & More(134)

134 Results
4 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
    (38)
    4 - 7 night minimum stay
    • 7 BR,
    • 3 BA,
    • Sleeps 16
      (17)
      2 - 7 night minimum stay
      • 6 BR,
      • 3 BA,
      • Sleeps 15
        (5)
        2 - 7 night minimum stay
        • 5 BR,
        • 2 BA,
        • 1 HF BA,
        • Sleeps 14
          (3)
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          2 night minimum stay
          • 2 BR,
          • 1 BA,
          • Sleeps 4
            7 night minimum stay
            • 2 BR,
            • 1 BA,
            • 1 HF BA,
            • Sleeps 4
              3 night minimum stay
              • 5 BR,
              • 3 BA,
              • Sleeps 10
                2 - 31 night minimum stay
                • 1 BR,
                • 1 BA,
                • Sleeps 2
                  (9)
                  1 - 31 night minimum stay
                  • 2 BR,
                  • 1 BA,
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                    (6)
                    7 night minimum stay
                    • 4 BR,
                    • 1 BA,
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                      (4)
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                      2 - 7 night minimum stay
                      • 5 BR,
                      • 2 BA,
                      • Sleeps 13
                        (6)
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                        7 night minimum stay
                        • 4 BR,
                        • 2 BA,
                        • Sleeps 9
                          7 night minimum stay
                          • 2 BR,
                          • 1 BA,
                          • Sleeps 5
                            (18)
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                            7 night minimum stay
                            • 3 BR,
                            • 2 BA,
                            • Sleeps 13
                              2 Reviews
                              7 night minimum stay
                              • 1 BR,
                              • 1 BA,
                              • Sleeps 2
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                                1 - 7 night minimum stay
                                • 4 BR,
                                • 3 BA,
                                • 1 HF BA,
                                • Sleeps 8
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                                  3 - 7 night minimum stay
                                  • 5 BR,
                                  • 7 BA,
                                  • Sleeps 14
                                    2 - 90 night minimum stay
                                    • 5 BR,
                                    • 3 BA,
                                    • Sleeps 10
                                      (4)
                                      $1,600 - $1,900
                                      per week
                                      7 - 30 night minimum stay
                                      • 2 BR,
                                      • 2 BA,
                                      • 1 HF BA,
                                      • Sleeps 6
                                        7 night minimum stay
                                        • 4 BR,
                                        • 2 BA,
                                        • Sleeps 11
                                          (9)
                                          $300 - $400
                                          per night
                                          2 - 7 night minimum stay
                                          • 3 BR,
                                          • 1 BA,
                                          • Sleeps 5
                                            4 - 7 night minimum stay
                                            • 3 BR,
                                            • 2 BA,
                                            • 1 HF BA,
                                            • Sleeps 8
                                              2 Reviews
                                              7 night minimum stay
                                              • 5 BR,
                                              • 2 BA,
                                              • 1 HF BA,
                                              • Sleeps 9
                                                • 4 BR,
                                                • 2 BA,
                                                • 1 HF BA,
                                                • Sleeps 14
                                                  1 Review
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                                                  3 night minimum stay
                                                  • 3 BR,
                                                  • 2 BA,
                                                  • Sleeps 6
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                                                    7 night minimum stay
                                                    • 1 BR,
                                                    • 1 BA,
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                                                      14 night minimum stay
                                                      • 4 BR,
                                                      • 2 BA,
                                                      • Sleeps 8
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                                                        7 night minimum stay
                                                        • 1 BR,
                                                        • 1 BA,
                                                        • Sleeps 2
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                                                          2 - 7 night minimum stay
                                                          • 2 BR,
                                                          • 1 BA,
                                                          • Sleeps 4
                                                            (10)
                                                            3 - 7 night minimum stay
                                                            • 4 BR,
                                                            • 1 BA,
                                                            • 1 HF BA,
                                                            • Sleeps 7
                                                              (18)
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