Vacation Rentals & Houses in Gloucester

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223 houses

    26

    Boulevard Bungalow: Steps away from Gloucester's fabled Stacy Boulevard.

    Cape Ann / Gloucester

    Gloucester house

    3 6 3 nights min

    • 3 bedrooms
    • sleeps 6
    • 3 nights min
    • Ask about children

    Price per night from

    $328

    Price per night from

    $328

    (6) Excellent 

      14

      Waterfront 2 Bedroom !

      Cape Ann / Gloucester

      Gloucester apartment

      2 4 min stay varies

      • 2 bedrooms
      • sleeps 4
      • min stay varies
      • Beach / lakeside relaxation
      • Nearest beach 2 mi
      • Child Friendly

      Price per night from

      $183

      Price per night from

      $183

        28

        Golden Sands at Good Harbor: Across the street from the beach

        Cape Ann / Gloucester

        Gloucester cottage

        7 12 min stay varies

        • 7 bedrooms
        • sleeps 12
        • min stay varies
        • Ask about children

        Price per night from

        $868

        Price per night from

        $868

        (1) Excellent 

          24

          Lovely 'Blue Heron Cottage' on Annisquam River!

          Cape Ann / Gloucester

          Gloucester cottage

          3 6 3 nights min

          • 3 bedrooms
          • sleeps 6
          • 3 nights min
          • Child Friendly
          • Air conditioning

          Price per night from

          $228

          Responds fast!
          avg. 19 minutes

          Price per night from

          $228

          (1) Excellent 

            12

            Waterfront Woodsy 3BR Cottage

            Cape Ann / Gloucester

            Gloucester house

            3 6 min stay varies

            • 3 bedrooms
            • sleeps 6
            • min stay varies
            • Nearest beach 2 mi
            • Child Friendly
            • Pet Friendly

            Price per night from

            $213

            Price per night from

            $213

              56

              Inviting apartment with harbor views, fireplace, patio, & gas grill!

              Cape Ann / Gloucester

              Gloucester house

              1 4 min stay varies

              • 1 bedroom
              • sleeps 4
              • min stay varies
              • Child Friendly
              • Car not necessary
              • Air conditioning

              Price per night from

              $196

              Price per night from

              $196

              (2) Very Good 

                18

                At the Footbridge entrance to Good Harbor Beach

                Cape Ann / Gloucester

                Gloucester house

                6 12 7 nights min

                • 6 bedrooms
                • sleeps 12
                • 7 nights min
                • Nearest beach 0 mi
                • Child Friendly
                • Private garden

                Price per night from

                $654

                Price per night from

                $654

                  33

                  Water's Edge: Direct waterfront on picturesque Goose Cove with dock

                  Cape Ann / Gloucester

                  Gloucester house

                  3 8 3 nights min

                  • 3 bedrooms
                  • sleeps 8
                  • 3 nights min
                  • Ask about children
                  • Air conditioning
                  • Pet Friendly

                  Price per night from

                  $453

                  Price per night from

                  $453

                    21

                    Cool Cove: Wingaersheek Beach plus your own private beach & all those views!

                    Cape Ann / Gloucester

                    Gloucester house

                    4 8 3 nights min

                    • 4 bedrooms
                    • sleeps 8
                    • 3 nights min
                    • Ask about children

                    Price per night from

                    $1,513

                    Price per night from

                    $1,513

                      39

                      Stunning Views - Spacious Home

                      Cape Ann / Gloucester

                      Gloucester house

                      3 8 7 nights min

                      • 3 bedrooms
                      • sleeps 8
                      • 7 nights min
                      • Beach / lakeside relaxation
                      • Nearest beach 0.8 mi

                      Price per night from

                      $573

                      Price per night from

                      $573

                        19

                        Salt Island Views: Walking distance to Good Harbor & Long Beach.

                        Cape Ann / Gloucester

                        Gloucester house

                        3 8 min stay varies

                        • 3 bedrooms
                        • sleeps 8
                        • min stay varies
                        • Ask about children

                        Price per night from

                        $532

                        Price per night from

                        $532

                        (3) Very Good 

                          26

                          Bohemia RETREAT Studio

                          Cape Ann / Gloucester

                          Gloucester apartment

                          1 3 3 nights min

                          • 1 bedroom
                          • sleeps 3
                          • 3 nights min
                          • Beach / lakeside relaxation
                          • Nearest beach 2 mi
                          • Private garden

                          Price per night from

                          $132

                          Responds fast!
                          avg. 2 hours 16 minutes

                          Price per night from

                          $132

                            31

                            Welcome Home: Walk to Gloucester's historic harbor and beaches.

                            Cape Ann / Gloucester

                            Gloucester house

                            5 12 min stay varies

                            • 5 bedrooms
                            • sleeps 12
                            • min stay varies
                            • Ask about children

                            Price per night from

                            $501

                            Price per night from

                            $501

                            (2) Very Good 

                              12

                              Vintage Home directly on the Annisquam River

                              Cape Ann / Gloucester

                              Gloucester house

                              6 12 4 nights min

                              • 6 bedrooms
                              • sleeps 12
                              • 4 nights min
                              • Beach / lakeside relaxation
                              • Ask about pets

                              Price per night from

                              $360

                              Price per night from

                              $360

                                7

                                Fabulous Waterfront 2 Bedroom - Boat dock option

                                Cape Ann / Gloucester

                                Gloucester apartment

                                2 4 30 nights min

                                • 2 bedrooms
                                • sleeps 4
                                • 30 nights min
                                • Ask about pets

                                Price per night from

                                $77

                                Price per night from

                                $77

                                  26

                                  Oceanside at Good Harbor: Walk 0.2 mi to the white sands of Good Harbor Beach

                                  Cape Ann / Gloucester

                                  Gloucester house

                                  5 9 min stay varies

                                  • 5 bedrooms
                                  • sleeps 9
                                  • min stay varies
                                  • Ask about children

                                  Price per night from

                                  $996

                                  Price per night from

                                  $996

                                    29

                                    Thurston Point: Waterfront rental with deepwater dock on Annisquam River!

                                    Cape Ann / Gloucester

                                    Gloucester cottage

                                    3 7 min stay varies

                                    • 3 bedrooms
                                    • sleeps 7
                                    • min stay varies
                                    • Ask about children

                                    Price per night from

                                    $322

                                    Price per night from

                                    $322

                                    (10) Excellent 

                                      40

                                      Gloucester Harborscape View 1 & 1/2 BR; walk to beach & town

                                      Cape Ann / Gloucester

                                      Gloucester apartment

                                      2 5 min stay varies

                                      • 2 bedrooms
                                      • sleeps 5
                                      • min stay varies
                                      • Beach / lakeside relaxation
                                      • Nearest beach 1 mi
                                      • Child Friendly

                                      Price per night from

                                      $138

                                      Price per night from

                                      $138

                                        25

                                        Seaside House: Good Harbor Beach and the Back Shore right outside

                                        Cape Ann / Gloucester

                                        Gloucester house

                                        4 10 min stay varies

                                        • 4 bedrooms
                                        • sleeps 10
                                        • min stay varies
                                        • Ask about children

                                        Price per night from

                                        $666

                                        Price per night from

                                        $666

                                          35

                                          Diamond in the Sky: Upscale townhouse near Good Harbor Beach.

                                          Cape Ann / Gloucester

                                          Gloucester condo

                                          3 7 3 nights min

                                          • 3 bedrooms
                                          • sleeps 7
                                          • 3 nights min
                                          • Ask about children
                                          • Air conditioning

                                          Price per night from

                                          $588

                                          Price per night from

                                          $588

                                            31

                                            Wonson Cove House: Rocky Neck, Eastern Point and Beaches

                                            Cape Ann / Gloucester

                                            Gloucester house

                                            4 10 min stay varies

                                            • 4 bedrooms
                                            • sleeps 10
                                            • min stay varies
                                            • Ask about children
                                            • Pet Friendly

                                            Price per night from

                                            $442

                                            Price per night from

                                            $442

                                              23

                                              Perrywinkle: Waterfront on Gloucester’s Rocky Neck.

                                              Cape Ann / Gloucester

                                              Gloucester house

                                              4 7 min stay varies

                                              • 4 bedrooms
                                              • sleeps 7
                                              • min stay varies
                                              • Ask about children

                                              Price per night from

                                              $487

                                              Price per night from

                                              $487

                                                20

                                                Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the beach!

                                                Cape Ann / Gloucester

                                                Gloucester apartment

                                                2 4 min stay varies

                                                • 2 bedrooms
                                                • sleeps 4
                                                • min stay varies
                                                • Ask about children

                                                Price per night from

                                                $208

                                                Price per night from

                                                $208

                                                  11

                                                  Cozy Guest Studio

                                                  Cape Ann / Gloucester

                                                  Gloucester studio

                                                  Studio 2 3 nights min

                                                  • Studio
                                                  • sleeps 2
                                                  • 3 nights min

                                                  Price per night from

                                                  $189

                                                  Price per night from

                                                  $189

                                                    18

                                                    Waterfront Vacation House w/ Dock

                                                    Cape Ann / Gloucester

                                                    Gloucester house

                                                    2 4 min stay varies

                                                    • 2 bedrooms
                                                    • sleeps 4
                                                    • min stay varies
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 2 mi
                                                    • Child Friendly

                                                    Price per night from

                                                    $344

                                                    Responds fast!
                                                    avg. 1 hour 26 minutes

                                                    Price per night from

                                                    $344

                                                      40

                                                      Annisquam Singing Pines: Private riverfront setting & tidal dock.

                                                      Cape Ann / Gloucester

                                                      Gloucester house

                                                      5 10 3 nights min

                                                      • 5 bedrooms
                                                      • sleeps 10
                                                      • 3 nights min
                                                      • Ask about children

                                                      Price per night from

                                                      $703

                                                      Price per night from

                                                      $703

                                                        18

                                                        Walk to Beach - Modern Apartment

                                                        Cape Ann / Gloucester

                                                        Gloucester house

                                                        1 2 2 nights min

                                                        • 1 bedroom
                                                        • sleeps 2
                                                        • 2 nights min
                                                        • Child Friendly
                                                        • Air conditioning

                                                        Price per night from

                                                        $160

                                                        Price per night from

                                                        $160

                                                          11

                                                          Stage Fort Park Place

                                                          Cape Ann / Gloucester

                                                          Gloucester house

                                                          5 14 min stay varies

                                                          • 5 bedrooms
                                                          • sleeps 14
                                                          • min stay varies
                                                          • Child Friendly
                                                          • Air conditioning

                                                          Price per night from

                                                          $308

                                                          Price per night from

                                                          $308

                                                            37

                                                            Sunset Cove: Waterfront home in Goose Cove section of Gloucester

                                                            Cape Ann / Gloucester

                                                            Gloucester house

                                                            2 6 3 nights min

                                                            • 2 bedrooms
                                                            • sleeps 6
                                                            • 3 nights min
                                                            • Ask about children

                                                            Price per night from

                                                            $533

                                                            Price per night from

                                                            $533

                                                              23

                                                              Sea Fox: Custom-designed home with rights to private Coffins Beach

                                                              Cape Ann / Gloucester

                                                              Gloucester house

                                                              4 8 min stay varies

                                                              • 4 bedrooms
                                                              • sleeps 8
                                                              • min stay varies
                                                              • Ask about children
                                                              • Air conditioning

                                                              Price per night from

                                                              $412

                                                              Price per night from

                                                              $412

                                                                35

                                                                Nature Lover's Paradise .5-1mile to beaches, nature walks, golf, museums, couple

                                                                Cape Ann / Gloucester

                                                                Gloucester house

                                                                2 4 2 nights min

                                                                • 2 bedrooms
                                                                • sleeps 4
                                                                • 2 nights min
                                                                • Child Friendly
                                                                • Air conditioning

                                                                Price per night from

                                                                $75

                                                                Price per night from

                                                                $75

                                                                (1) Excellent 

                                                                  12

                                                                  Close to Half Moon Bay

                                                                  Cape Ann / Gloucester

                                                                  Gloucester apartment

                                                                  1 2 2 nights min

                                                                  • 1 bedroom
                                                                  • sleeps 2
                                                                  • 2 nights min
                                                                  • Nearest beach 1 mi

                                                                  Price per night from

                                                                  $142

                                                                  Price per night from

                                                                  $142

                                                                    21

                                                                    Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches

                                                                    Cape Ann / Gloucester

                                                                    Gloucester house

                                                                    2 4 min stay varies

                                                                    • 2 bedrooms
                                                                    • sleeps 4
                                                                    • min stay varies
                                                                    • Ask about children
                                                                    • Pet Friendly

                                                                    Price per night from

                                                                    $218

                                                                    Price per night from

                                                                    $218

                                                                      57

                                                                      Strawberry Cove House: Multi-level waterfront home

                                                                      Cape Ann / Gloucester

                                                                      Gloucester house

                                                                      4 10 3 nights min

                                                                      • 4 bedrooms
                                                                      • sleeps 10
                                                                      • 3 nights min
                                                                      • Ask about children

                                                                      Price per night from

                                                                      $943

                                                                      Price per night from

                                                                      $943

                                                                        12

                                                                        Good Harbor Escape: Swim or walk over to Good Harbor Beach!

                                                                        Cape Ann / Gloucester

                                                                        Gloucester house

                                                                        3 6 3 nights min

                                                                        • 3 bedrooms
                                                                        • sleeps 6
                                                                        • 3 nights min
                                                                        • Ask about children

                                                                        Price per night from

                                                                        $353

                                                                        Price per night from

                                                                        $353

                                                                          9

                                                                          Coastal, Cute & Cozy|Close to Everything

                                                                          Cape Ann / Gloucester

                                                                          Gloucester apartment

                                                                          1 2 7 nights min

                                                                          • 1 bedroom
                                                                          • sleeps 2
                                                                          • 7 nights min
                                                                          • Pet Friendly

                                                                          Price per night from

                                                                          $126

                                                                          Price per night from

                                                                          $126

                                                                            74

                                                                            Modern beach home w/ deck, central AC, & free WiFi, steps from the ocean

                                                                            Cape Ann / Gloucester

                                                                            Gloucester house

                                                                            3 6 min stay varies

                                                                            • 3 bedrooms
                                                                            • sleeps 6
                                                                            • min stay varies
                                                                            • Child Friendly
                                                                            • Car not necessary
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $156

                                                                            Price per night from

                                                                            $156

                                                                              20

                                                                              Long Beach House: Large, comfortable home just 285 feet from the white sands!

                                                                              Cape Ann / Gloucester

                                                                              Gloucester house

                                                                              5 10 min stay varies

                                                                              • 5 bedrooms
                                                                              • sleeps 10
                                                                              • min stay varies
                                                                              • Ask about children
                                                                              • Pet Friendly

                                                                              Price per night from

                                                                              $397

                                                                              Price per night from

                                                                              $397

                                                                              About Gloucester

                                                                              Located on the northern shores of Massachusetts, the town of Gloucester is a vacation paradise that generations of travelers return to every year. The winding streets of this historic town are lined with quaint shops, interesting museums, charming cafes, and unforgettable seafood restaurants. Come here to experience the beautiful rocky coastlines and soft sand beaches of Massachusetts. Hike the trails and stop at breathtaking overlooks with views of the Atlantic Ocean. Visit historic homes and lighthouses. Spend the afternoon swimming, snorkeling, or relaxing on a pristine beach. And then go home at night to your own private vacation rental and host dinner for your family and friends. Many vacation rentals in Gloucester are less expensive than hotels and offer more space and better amenities. Wake up in the morning and watch the sun rise from the deck of your beach condo or summer house, then head downtown to spend the day exploring and making fun vacation memories.

                                                                              Here are a few additional suggestions for your trip:

                                                                              • Take a brewery tour: Gloucester is the traditional home of several long established breweries and craft distilleries. Taste some of the area's award winning artisanal spirits.
                                                                              • Tour Hammond Castle: This extraordinary structure was once the home of John Hays Jr., a wealthy eccentric who amassed an extensive collection of medieval artifacts.
                                                                              • Visit the Fisherman's Memorial Monument: This fascinating memorial was built in 1925 to honor all the fishermen who have been lost at sea since the 17th century.
                                                                              • Play on the beach: Swim, build a sandcastle, or just relax on Good Harbor Beach or Stage Fort Park and Beach, two of the most popular beach destinations in the area.
                                                                              • Visit the Rocky Neck Art Colony: This is the oldest established colony for artists in the United States and has been a destination for art lovers since the 1840s.
                                                                              • Visit the Beauport Museum or the Cape Ann Historical Museum: Learn more about the fascinating history of Cape Ann with the changing exhibits of these popular museums.

                                                                              Gloucester offers an ideal scenic back drop for whatever vacation activities you have in mind. The best way to enjoy it all is with a stay in your own apartment rental or summer condo. Find a luxury vacation rental just a few steps from the beach that offers all the amenities you and your family need. While you're visiting Gloucester, be sure to plan day trips to coastal destinations nearby like Cape Cod and Plymouth.