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(133)

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family View A
    6 Bedrooms,
  • 3 Bathrooms
  • , Sleeps 15
2 - 7 night minimum stay
  • 6 BR,
  • 3 BA,
  • Sleeps 15
#951090
    2 Reviews
    Large, charming home near Lighthouse Beach (in the heart of Annisquam)
      5 Bedrooms,
    • 5 Bathrooms
    • 3 Half Baths
    • , Sleeps 14
    7 night minimum stay
    • 5 BR,
    • 5 BA,
    • 3 HF BA,
    • Sleeps 14
    #294286
      (7)
      Breathtaking ocean views and your own private beach.
        4 Bedrooms,
      • 3 Bathrooms
      • 1 Half Bath
      • , Sleeps 10
      7 night minimum stay
      • 4 BR,
      • 3 BA,
      • 1 HF BA,
      • Sleeps 10
      #376940
        Water Views overlooking Gloucester's inner harbor
          3 Bedrooms,
        • 2 Bathrooms
        • 1 Half Bath
        • , Sleeps 6
        3 night minimum stay
        • 3 BR,
        • 2 BA,
        • 1 HF BA,
        • Sleeps 6
        #192597
          (29)
          Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family
            5 Bedrooms,
          • 2 Bathrooms
          • 1 Half Bath
          • , Sleeps 14
          2 - 7 night minimum stay
          • 5 BR,
          • 2 BA,
          • 1 HF BA,
          • Sleeps 14
          #3523865
            1 Review
            Panoramic Ocean Views, Magnificent 3 Bedroom Home
              3 Bedrooms,
            • 1 Bathroom
            • , Sleeps 6
            7 night minimum stay
            • 3 BR,
            • 1 BA,
            • Sleeps 6
            #3537978
              1 Review
              Stunning oceanfront home and location with views, land, beach, tennis on estate
                5 Bedrooms,
              • 3 Bathrooms
              • , Sleeps 10
              7 night minimum stay
              • 5 BR,
              • 3 BA,
              • Sleeps 10
              #334284
                (4)
                Charming Carriage House in Annisquam Village with tennis court
                  2 Bedrooms,
                • 1 Bathroom
                • , Sleeps 7
                • 2 BR,
                • 1 BA,
                • Sleeps 7
                #993921
                  Private, spacious waterfront home on prestigious Eastern Point - pool, hot tub
                    6 Bedrooms,
                  • 3 Bathrooms
                  • , Sleeps 13
                  4 - 7 night minimum stay
                  • 6 BR,
                  • 3 BA,
                  • Sleeps 13
                  #294953
                    2 Reviews
                    Share Amazing Sunsets On Ipswich Bay With Family And Friends
                      3 Bedrooms,
                    • 2 Bathrooms
                    • 1 Half Bath
                    • , Sleeps 8
                    3 - 7 night minimum stay
                    • 3 BR,
                    • 2 BA,
                    • 1 HF BA,
                    • Sleeps 8
                    #476653vb
                      Romantic Hideaway near Beach in Lanesville section of Gloucseter
                        2 Bedrooms,
                      • 2 Bathrooms
                      • , Sleeps 4
                      3 night minimum stay
                      • 2 BR,
                      • 2 BA,
                      • Sleeps 4
                      #3550218
                        Summer House Rental with partial Ocean View near Good Harbor Beach
                          4 Bedrooms,
                        • 1 Bathroom
                        • , Sleeps 7
                        6 night minimum stay
                        • 4 BR,
                        • 1 BA,
                        • Sleeps 7
                        #106360
                          (4)
                          A Sunset Serenade - Delightful Studio with Deck Overlooking Scenic Harbor
                            1 Bedrooms,
                          • 1 Bathroom
                          • , Sleeps 2
                          7 night minimum stay
                          • 1 BR,
                          • 1 BA,
                          • Sleeps 2
                          #120975
                            (40)
                            Buoy 23: Direct waterfront cottage with deepwater dock on the Annisquam River
                              4 Bedrooms,
                            • 1 Bathroom
                            • 1 Half Bath
                            • , Sleeps 7
                            7 night minimum stay
                            • 4 BR,
                            • 1 BA,
                            • 1 HF BA,
                            • Sleeps 7
                            #997308
                              (15)
                              Romantic SUMMERWIND COTTAGE - Scenic Harbor View w/Large Deck
                                2 Bedrooms,
                              • 1 Bathroom
                              • , Sleeps 5
                              7 night minimum stay
                              • 2 BR,
                              • 1 BA,
                              • Sleeps 5
                              #953745
                                (21)
                                Romantic three season cottage
                                  2 Bedrooms,
                                • 1 Bathroom
                                • , Sleeps 4
                                2 - 7 night minimum stay
                                • 2 BR,
                                • 1 BA,
                                • Sleeps 4
                                #376520
                                  (8)
                                  Rosemarc House: Direct beachfront on Good Harbor!
                                    3 Bedrooms,
                                  • 3 Bathrooms
                                  • 1 Half Bath
                                  • , Sleeps 6
                                  7 night minimum stay
                                  • 3 BR,
                                  • 3 BA,
                                  • 1 HF BA,
                                  • Sleeps 6
                                  #997464
                                    (4)
                                    Somsersette: 5BR with views on Brier Neck! Only 0.1 mile to Good Harbor Beach
                                      5 Bedrooms,
                                    • 2 Bathrooms
                                    • 1 Half Bath
                                    • , Sleeps 9
                                    7 night minimum stay
                                    • 5 BR,
                                    • 2 BA,
                                    • 1 HF BA,
                                    • Sleeps 9
                                    #997468
                                      (4)
                                      Idyllic ocean-front Gloucester cottage
                                        2 Bedrooms,
                                      • 2 Bathrooms
                                      • , Sleeps 7
                                      3 - 242 night minimum stay
                                      • 2 BR,
                                      • 2 BA,
                                      • Sleeps 7
                                      #182967
                                        (9)
                                        Wingaersheek Beach (Private Section) Bungalow -
                                          3 Bedrooms,
                                        • 1 Bathroom
                                        • , Sleeps 10
                                        7 night minimum stay
                                        • 3 BR,
                                        • 1 BA,
                                        • Sleeps 10
                                        #108307
                                          Beachcomber Cottage 'Long Beach' - Steps to White Sandy Beach
                                            3 Bedrooms,
                                          • 2 Bathrooms
                                          • , Sleeps 6
                                          7 night minimum stay
                                          • 3 BR,
                                          • 2 BA,
                                          • Sleeps 6
                                          #967257
                                            (3)
                                            Dale's Cove House: Waterfront and private beach!
                                              6 Bedrooms,
                                            • 6 Bathrooms
                                            • 1 Half Bath
                                            • , Sleeps 10
                                            7 night minimum stay
                                            • 6 BR,
                                            • 6 BA,
                                            • 1 HF BA,
                                            • Sleeps 10
                                            #997470
                                              2 Reviews
                                              Waterfront, elegant 7 year old Contemporary. Serene, open, master suite, FP,dock
                                                3 Bedrooms,
                                              • 2 Bathrooms
                                              • , Sleeps 6
                                              7 night minimum stay
                                              • 3 BR,
                                              • 2 BA,
                                              • Sleeps 6
                                              #296872
                                                (3)
                                                Kris' Kottage: Wonderfully located cottage and just 0.2 miles to Long Beach!
                                                  3 Bedrooms,
                                                • 1 Bathroom
                                                • , Sleeps 6
                                                7 - 56 night minimum stay
                                                • 3 BR,
                                                • 1 BA,
                                                • Sleeps 6
                                                #3523223
                                                  (3)
                                                  Direct Waterfront Home with Sweeping Ocean Views, Deep Water Dock
                                                    4 Bedrooms,
                                                  • 1 Bathroom
                                                  • 1 Half Bath
                                                  • , Sleeps 10
                                                  7 night minimum stay
                                                  • 4 BR,
                                                  • 1 BA,
                                                  • 1 HF BA,
                                                  • Sleeps 10
                                                  #168659
                                                    (5)
                                                    Beachmont: Classic New England beauty! 0.2 miles from Cressy Beach
                                                      5 Bedrooms,
                                                    • 2 Bathrooms
                                                    • , Sleeps 8
                                                    7 - 56 night minimum stay
                                                    • 5 BR,
                                                    • 2 BA,
                                                    • Sleeps 8
                                                    #997280
                                                      Sun-filled waterfront house with sweeping views of Annisquam, with private dock
                                                        2 Bedrooms,
                                                      • 2 Bathrooms
                                                      • , Sleeps 4
                                                      7 - 84 night minimum stay
                                                      • 2 BR,
                                                      • 2 BA,
                                                      • Sleeps 4
                                                      #318709
                                                        2 Reviews
                                                        'Ever Nice' in Diamond Cove - Annisquam
                                                          4 Bedrooms,
                                                        • 1 Bathroom
                                                        • 1 Half Bath
                                                        • , Sleeps 10
                                                        $1,050 - $1,750
                                                        per week
                                                        7 night minimum stay
                                                        • 4 BR,
                                                        • 1 BA,
                                                        • 1 HF BA,
                                                        • Sleeps 10
                                                        #136405
                                                          (3)
                                                          Lobster Cove House: Picturesque views of the cove! Walk to Lighthouse Beach!
                                                            4 Bedrooms,
                                                          • 2 Bathrooms
                                                          • 1 Half Bath
                                                          • , Sleeps 8
                                                          7 night minimum stay
                                                          • 4 BR,
                                                          • 2 BA,
                                                          • 1 HF BA,
                                                          • Sleeps 8
                                                          #3523224
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