Vacation Rentals & Houses in Cape Ann

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218 houses

(1) Excellent 

    6

    One Bedroom Loft Apartment B at Cedar Hill Farm B & B

    Cape Ann / Essex

    Essex apartment

    1 4 2 nights min

    • 1 bedroom
    • sleeps 4
    • 2 nights min
    • Child Friendly
    • Air conditioning
    • Pet Friendly

    Price per night from

    $201

    Price per night from

    $201

      44

      40% off regular rate: Wonderful 4 Bedroom, 2 Full Bath Restored 1917 Home

      Cape Ann / Manchester-by-the-Sea

      Manchester-by-the-Sea house

      4 7 5 nights min

      • 4 bedrooms
      • sleeps 7
      • 5 nights min
      • Child Friendly

      Price per night from

      $457

      Price per night from

      $457

      (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

        $184

        Price per night from

        $184

          29

          The Rockporter: Enjoy beautiful views of Pigeon Cove Harbor.

          Cape Ann / Rockport

          Rockport house

          4 7 3 nights min

          • 4 bedrooms
          • sleeps 7
          • 3 nights min
          • Ask about children

          Price per night from

          $513

          Price per night from

          $513

            13

            The Friendship Room at Cedar Hill Farm B & B

            Cape Ann / Essex

            Essex b and b

            1 3 2 nights min

            • 1 bedroom
            • sleeps 3
            • 2 nights min
            • Child Friendly
            • Air conditioning
            • Private garden

            Price per night from

            $172

            Price per night from

            $172

              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

                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

                (5) Excellent 

                  21

                  Family Friendly Apartment, Short Walk to Beach/Downtown, Parking, WiFi, Grill

                  Cape Ann / Rockport

                  Rockport apartment

                  2 7 2 nights min

                  • 2 bedrooms
                  • sleeps 7
                  • 2 nights min
                  • Beach / lakeside relaxation
                  • Nearest beach 0.3 mi
                  • Child Friendly

                  Price per night from

                  $228

                  Price per night from

                  $228

                    15

                    Beautiful First Floor 2 BR Condo in Manchester

                    Cape Ann / Manchester-by-the-Sea

                    Manchester-by-the-Sea townhouse

                    2 4 7 nights min

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

                    Price per night from

                    $245

                    Price per night from

                    $245

                    (2) Very Good 

                      12

                      Beachcomber Suite

                      Cape Ann / Rockport

                      Rockport house

                      1 2 2 nights min

                      • 1 bedroom
                      • sleeps 2
                      • 2 nights min
                      • Car not necessary
                      • Air conditioning
                      • Private garden

                      Price per night from

                      $201

                      Responds fast!
                      avg. 33 minutes

                      Price per night from

                      $201

                      (2) Excellent 

                        15

                        Back Beach

                        Cape Ann / Rockport

                        Rockport house

                        4 8 7 nights min

                        • 4 bedrooms
                        • sleeps 8
                        • 7 nights min
                        • Child Friendly
                        • Air conditioning
                        • Ask about pets

                        Price per night from

                        $491

                        Responds fast!
                        avg. 1 hour 6 minutes

                        Price per night from

                        $491

                          16

                          Second Floor: 2+ Bedroom, 1.25 Bath

                          Cape Ann / Manchester-by-the-Sea

                          Manchester-by-the-Sea condo

                          3 5 4 nights min

                          • 3 bedrooms
                          • sleeps 5
                          • 4 nights min
                          • Child Friendly

                          Price per night from

                          $287

                          Price per night from

                          $287

                            18

                            GLORIOUS OCEAN VIEWS FROM LOBLOLLY COVE - DECK - SEASIDE PATH TO BEACH AND TOWN

                            Cape Ann / Rockport

                            Rockport apartment

                            2 3 7 nights min

                            • 2 bedrooms
                            • sleeps 3
                            • 7 nights min
                            • Beach / lakeside relaxation
                            • Child Friendly
                            • Air conditioning

                            Price per night from

                            $245

                            Responds fast!
                            avg. 37 minutes

                            Price per night from

                            $245

                            (1) Excellent 

                              24

                              18th Century Cottage with attached guest suite

                              Cape Ann / Rockport

                              Rockport cottage

                              2 6 7 nights min

                              • 2 bedrooms
                              • sleeps 6
                              • 7 nights min
                              • Child Friendly
                              • Ask about pets

                              Price per night from

                              $213

                              Price per night from

                              $213

                                26

                                Oceans Views And Minutes Walk To Beach

                                Cape Ann / Rockport

                                Rockport house

                                4 8 3 nights min

                                • 4 bedrooms
                                • sleeps 8
                                • 3 nights min
                                • Child Friendly

                                Price per night from

                                $327

                                Price per night from

                                $327

                                (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

                                  $653

                                  Price per night from

                                  $653

                                    14

                                    Granite Cottage: Charming cottage in Rockport with private deck and views

                                    Cape Ann / Rockport

                                    Rockport cottage

                                    1 4 3 nights min

                                    • 1 bedroom
                                    • sleeps 4
                                    • 3 nights min
                                    • Ask about children
                                    • Pet Friendly

                                    Price per night from

                                    $253

                                    Price per night from

                                    $253

                                    (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

                                        21

                                        Poolside Summers: Swim in the private in-ground pool or walk to the beach

                                        Cape Ann / Rockport

                                        Rockport house

                                        4 8 min stay varies

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

                                        Price per night from

                                        $487

                                        Price per night from

                                        $487

                                          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

                                            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

                                            Responds fast!
                                            avg. 2 hours 57 minutes

                                            Price per night from

                                            $196

                                              0

                                              NEW LISTING! Quaint getaway w/ kitchen & lush yard - near beach & town, dogs OK!

                                              Cape Ann / Rockport

                                              Rockport house

                                              3 6 min stay varies

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

                                              Price per night from

                                              $113

                                              Responds fast!
                                              avg. 2 hours 24 minutes

                                              Price per night from

                                              $113

                                              (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. 33 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

                                                    23

                                                    North Seas Cottage: Water views in serene Pigeon Cove

                                                    Cape Ann / Rockport

                                                    Rockport cottage

                                                    2 4 min stay varies

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

                                                    Price per night from

                                                    $279

                                                    Price per night from

                                                    $279

                                                      14

                                                      Renovated 19th century home in pastoral setting

                                                      Cape Ann / Essex

                                                      Essex apartment

                                                      2 6 3 nights min

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

                                                      Price per night from

                                                      $179

                                                      Price per night from

                                                      $179

                                                        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

                                                          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

                                                          (4) Excellent 

                                                            14

                                                            Captain Quarters

                                                            Cape Ann / Rockport

                                                            Rockport b and b

                                                            1 2 2 nights min

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

                                                            Price per night from

                                                            $184

                                                            Responds fast!
                                                            avg. 33 minutes

                                                            Price per night from

                                                            $184

                                                            (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

                                                              (2) Excellent 

                                                                18

                                                                GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM

                                                                Cape Ann / Rockport

                                                                Rockport cottage

                                                                2 4 min stay varies

                                                                • 2 bedrooms
                                                                • sleeps 4
                                                                • min stay varies
                                                                • Beach / lakeside relaxation
                                                                • Nearest beach 0.5 mi
                                                                • Child Friendly

                                                                Price per night from

                                                                $216

                                                                Responds fast!
                                                                avg. 37 minutes

                                                                Price per night from

                                                                $216

                                                                  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

                                                                      14

                                                                      Coolest House in Rockport: Newly Renovated Home Overlooking Pigeon Cove Floor 1

                                                                      Cape Ann / Rockport

                                                                      Rockport house

                                                                      3 6 7 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 6
                                                                      • 7 nights min
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $372

                                                                      Price per night from

                                                                      $372

                                                                      (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

                                                                          34

                                                                          Happy Days Cottage: Charming Folly Cove house with waterfront deck

                                                                          Cape Ann / Rockport

                                                                          Rockport cottage

                                                                          4 7 3 nights min

                                                                          • 4 bedrooms
                                                                          • sleeps 7
                                                                          • 3 nights min
                                                                          • Ask about children
                                                                          • Pet Friendly

                                                                          Price per night from

                                                                          $313

                                                                          Price per night from

                                                                          $313

                                                                            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

                                                                            $343

                                                                            Responds fast!
                                                                            avg. 1 hour 26 minutes

                                                                            Price per night from

                                                                            $343

                                                                              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

                                                                              About Cape Ann

                                                                              Cape Ann, Massachusetts

                                                                              This rocky cape in Northeastern Massachusetts lies around 30 miles northeast of the city of Boston. Home to the historic port of Gloucester and pretty towns and villages including Rockport, Essex and Manchester-by-the-Sea, you’re sure to find your perfect seaside vacation property in Cape Ann with FlipKey.

                                                                              About Cape Ann, Massachusetts

                                                                              Cape Ann has a rich history, and Gloucester is one of the oldest towns in New England, founded in 1623. The town’s economy has relied on fishing for over 400 years, and wherever you go on the Cape, you’ll see fishing boats and creels – the seafood here is as fresh as it comes!

                                                                              With its gorgeous, white sandy beaches, watersports, fishing and whale watching, a vacation on Cape Ann has something to offer everyone, from families to couples looking for a romantic retreat away from the hustle and bustle of Boston.

                                                                              While you’re here, don’t miss out on a trip to Essex, the Home of the Fried Clam. Dipped in milk and flour, deep-fried and served with tartar sauce, these are a local specialty you simply have to try!

                                                                              What to do in Cape Ann, Massachusetts

                                                                              Spend your days relaxing on one of Cape Ann’s beautiful beaches. The soft white sands of Good Harbor ensure it’s a popular choice, whilst Front Beach (Rockport) is great for swimming and Singing Beach (Manchester-by-the-Sea) is a hidden gem!

                                                                              Explore the historic town of Gloucester, home to America’s oldest seaport. Take a self-guided tour of the Gloucester Harbor Walk with its 42 story markers highlighting local history and culture, or visit one of the five lighthouses dotted along the coastline.

                                                                              Visit the Shipbuilding Museum in Essex for a fascinating insight into the shipbuilding industry that once put this town on the map, or shop for antiques in the town center. Or head for Manchester-by-the-Sea, when the Festival by the Sea takes place every July. This colorful celebration of local art, culture, music and food is fun for the whole family.

                                                                              Top travel tips for Cape Ann

                                                                              If you’re flying to Cape Ann, the nearest airport is Boston Logan International, just 42 miles from the center of Gloucester.

                                                                              Come in the summer months if you want to enjoy whale watching tours. Cape Ann is located midway between two whale feeding grounds where you can also spot dolphins and sea birds.

                                                                              With average temperatures of 75 degrees Fahrenheit in July and August, summer is the best time to visit, although spring in Cape Ann is also quite warm and sunny.

                                                                              With white sandy beaches, a rich seafaring history and some of the freshest seafood around, a vacation to Cape Ann can be a relaxing or activity-packed as you want it to be. Why not browse FlipKey’s range of vacation rentals for your perfect property in Rockport, Gloucester or Essex today?