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601 Houses

    15

    Stunning Studio in Woods

    Massachusetts / Wenham

    Wenham apartment

    1 2 30 nights min

    • 1 bedroom
    • sleeps 2
    • 30 nights min
    • Beach / lakeside relaxation
    • Air conditioning

    Price per night from

    $86

    Price per night from

    $86

    Great rentals within 20 miles that match your search

    Distance approx 6.15 km from Wenham Show on Map

      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

      $252

      Price per night from

      $252

      Distance approx 14.62 km from Wenham

        20

        Big Ole Single Family House

        Massachusetts / Newburyport

        Newburyport house

        4 14 1 night min

        • 4 bedrooms
        • sleeps 14
        • 1 night min
        • Child Friendly
        • Air conditioning
        • Pet Friendly

        Price per night from

        $647

        Price per night from

        $647

        Distance approx 14.01 km from Wenham

        (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

          $505

          Responds fast!
          avg. 1 hour 29 minutes

          Price per night from

          $505

          Distance approx 12.83 km from Wenham

          (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

            $672

            Price per night from

            $672

            Distance approx 18.86 km from Wenham

            (1) Excellent 

              12

              New, Super Cool 2 bedroom steps to Fanuile Hall

              Massachusetts / Boston

              Boston apartment

              2 4 min stay varies

              • 2 bedrooms
              • sleeps 4
              • min stay varies
              • Suitable for children age 5+
              • Car not necessary
              • Air conditioning
              “Perfect location, great space, great service, and would stay there again.” The rental agent, Elyne, could not have been more helpful from beginning to end. She is responsive and trustworthy. My husband left his prescription eyeglasses in the apartmen
              …see more

              Price per night from

              $330

              Price per night from

              $330

              Distance approx 10.34 km from Wenham

              (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

                $234

                Responds fast!
                avg. 13 minutes

                Price per night from

                $234

                Distance approx 13.12 km from Wenham

                  57

                  Oceanfront Sunsets; large family cottage included

                  Massachusetts / Ipswich

                  Ipswich cottage

                  4 8 min stay varies

                  • 4 bedrooms
                  • sleeps 8
                  • min stay varies
                  • Beach / lakeside relaxation
                  • Nearest beach 5 mi
                  • Child Friendly

                  Price per night from

                  $353

                  Price per night from

                  $353

                  Distance approx 18.86 km from Wenham

                    10

                    Beautiful, new, one bedroom, amazing location

                    Massachusetts / Boston

                    Boston apartment

                    1 3 3 nights min

                    • 1 bedroom
                    • sleeps 3
                    • 3 nights min
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $206

                    Price per night from

                    $206

                    Distance approx 6.14 km from Wenham Show on Map

                      9

                      New England Room+Bkft (E)

                      Massachusetts / Ipswich

                      Ipswich b and b

                      1 2 2 nights min

                      • 1 bedroom
                      • sleeps 2
                      • 2 nights min
                      • Beach / lakeside relaxation
                      • Ask about children
                      • Air conditioning

                      Price per night from

                      $225

                      Price per night from

                      $225

                      Distance approx 8.04 km from Wenham Show on Map

                        27

                        Priceless Ocean View 2BR + porch bed

                        Massachusetts / Ipswich

                        Ipswich house

                        2 4 min stay varies

                        • 2 bedrooms
                        • sleeps 4
                        • min stay varies
                        • Child Friendly
                        • Air conditioning

                        Price per night from

                        $224

                        Price per night from

                        $224

                        Distance approx 7.66 km from Wenham Show on Map

                          23

                          Exclusive Lifestyle near the Ocean

                          Massachusetts / Marblehead

                          Marblehead house

                          5 10 min stay varies

                          • 5 bedrooms
                          • sleeps 10
                          • min stay varies
                          • Child Friendly
                          • Air conditioning
                          • Pet Friendly

                          Price per night from

                          $942

                          Price per night from

                          $942

                          Distance approx 18.51 km from Wenham

                            18

                            North End Luxurious Modern One Bedroom Condo

                            Massachusetts / Boston

                            Boston condo

                            1 3 3 nights min

                            • 1 bedroom
                            • sleeps 3
                            • 3 nights min

                            Price per night from

                            $294

                            Responds fast!
                            avg. 2 hours 26 minutes

                            Price per night from

                            $294

                            Distance approx 12.76 km from Wenham

                              11

                              Cozy Guest Studio

                              Cape Ann / Gloucester

                              Gloucester studio

                              Studio 2 3 nights min

                              • Studio
                              • sleeps 2
                              • 3 nights min

                              Price per night from

                              $195

                              Price per night from

                              $195

                              Distance approx 14.41 km from Wenham

                                5

                                Gorgeous 1 Bed 1 Bath

                                Massachusetts / Wilmington

                                Wilmington apartment

                                1 2 1 night min

                                • 1 bedroom
                                • sleeps 2
                                • 1 night min
                                • Ask about children
                                • Ask about pets

                                Price per night from

                                $177

                                Price per night from

                                $177

                                Distance approx 14.42 km from Wenham

                                  21

                                  Coolest House in Rockport: Overlooking Pigeon Cove and the Ocean

                                  Cape Ann / Rockport

                                  Rockport condo

                                  3 8 7 nights min

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

                                  Price per night from

                                  $412

                                  Price per night from

                                  $412

                                  Distance approx 5.59 km from Wenham Show on Map

                                    24

                                    NEW! Ipswich Townhome w/4-Season Porch & Yard!

                                    Massachusetts / Ipswich

                                    Ipswich townhouse

                                    1 6 min stay varies

                                    • 1 bedroom
                                    • sleeps 6
                                    • min stay varies
                                    • Child Friendly
                                    • Air conditioning
                                    • Pet Friendly

                                    Price per night from

                                    $83

                                    Responds fast!
                                    avg. 8 minutes

                                    Price per night from

                                    $83

                                    Distance approx 14.38 km from Wenham

                                    (1) Very Good 

                                      15

                                      A Year-Round Vacation Home

                                      Cape Ann / Rockport

                                      Rockport house

                                      3 5 3 nights min

                                      • 3 bedrooms
                                      • sleeps 5
                                      • 3 nights min
                                      • Child Friendly
                                      • Private garden

                                      Price per night from

                                      $294

                                      Responds fast!
                                      avg. 3 hours 24 minutes

                                      Price per night from

                                      $294

                                      Distance approx 19.18 km from Wenham

                                        21

                                        Simple studio in Beacon Hill

                                        Massachusetts / Boston

                                        Boston studio

                                        Studio 2 1 night min

                                        • Studio
                                        • sleeps 2
                                        • 1 night min
                                        • Child Friendly
                                        • Pet Friendly

                                        Price per night from

                                        $234

                                        Responds fast!
                                        avg. 3 hours 55 minutes

                                        Price per night from

                                        $234

                                        Distance approx 19.24 km from Wenham

                                        (2) Excellent 

                                          7

                                          3br/1140sf Cambridge Winter Rental By Harvard Sq.

                                          Massachusetts / Cambridge

                                          Cambridge apartment

                                          3 4 90 nights min

                                          • 3 bedrooms
                                          • sleeps 4
                                          • 90 nights min
                                          • Child Friendly
                                          • Ask about pets

                                          Price per night from

                                          $133

                                          Price per night from

                                          $133

                                          Distance approx 13.14 km from Wenham

                                            12

                                            Rockwood Cottage

                                            Cape Ann / Gloucester

                                            Gloucester house

                                            2 4 4 nights min

                                            • 2 bedrooms
                                            • sleeps 4
                                            • 4 nights min
                                            • Child Friendly
                                            • Private garden

                                            Price per night from

                                            $442

                                            Price per night from

                                            $442

                                            Distance approx 11.7 km from Wenham

                                              23

                                              Relax at Rocky Neck Hideaway

                                              Cape Ann / Gloucester

                                              Gloucester townhouse

                                              1 3 7 nights min

                                              • 1 bedroom
                                              • sleeps 3
                                              • 7 nights min
                                              • Child Friendly
                                              • Air conditioning

                                              Price per night from

                                              $152

                                              Price per night from

                                              $152

                                              Distance approx 19.12 km from Wenham

                                                22

                                                H2 Unit #1 Executive Large Townhouse Style near Harvard Square

                                                Massachusetts / Boston

                                                Boston apartment

                                                1 4 6 nights min

                                                • 1 bedroom
                                                • sleeps 4
                                                • 6 nights min
                                                • Nearest beach 6 mi
                                                • Child Friendly
                                                • Car not necessary

                                                Price per night from

                                                $530

                                                Price per night from

                                                $530

                                                Distance approx 14.4 km from Wenham

                                                  15

                                                  Can't wait to return to Four Winds in Rockport, MA

                                                  Cape Ann / Rockport

                                                  Rockport condo

                                                  2 4 2 nights min

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

                                                  Price per night from

                                                  $294

                                                  Price per night from

                                                  $294

                                                  Distance approx 18.83 km from Wenham

                                                    8

                                                    Stunning west end beauty walk to MGH and cambridg

                                                    Massachusetts / Boston

                                                    Boston apartment

                                                    1 2 30 nights min

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

                                                    Price per night from

                                                    $138

                                                    Price per night from

                                                    $138

                                                    Distance approx 11.53 km from Wenham

                                                      8

                                                      Humble Suite

                                                      Cape Ann / Gloucester

                                                      Gloucester guest house

                                                      2 5 min stay varies

                                                      • 2 bedrooms
                                                      • sleeps 5
                                                      • min stay varies
                                                      • Child Friendly

                                                      Price per night from

                                                      $212

                                                      Price per night from

                                                      $212

                                                      Distance approx 19.11 km from Wenham

                                                        13

                                                        Seaport Luxe Condos Studio 7

                                                        Massachusetts / Boston

                                                        Boston studio

                                                        Studio 3 min stay varies

                                                        • Studio
                                                        • sleeps 3
                                                        • min stay varies
                                                        • Child Friendly

                                                        Price per night from

                                                        $116

                                                        Price per night from

                                                        $116

                                                        Distance approx 19.12 km from Wenham

                                                        (42) Excellent 

                                                        Certificate of Excellence

                                                          10

                                                          Beacon Hill -- "Luci Bella" elegant one bedroom

                                                          Massachusetts / Boston

                                                          Boston apartment

                                                          1 3 30 nights min

                                                          • 1 bedroom
                                                          • sleeps 3
                                                          • 30 nights min
                                                          • Car not necessary
                                                          • Air conditioning
                                                          “Seriously fantastic!” We would sincerely like to thank owner Paul. This was a truly great holiday. I lived in Boston some time ago and had managed to obtain some cheap flights back for a weeks vacation with my partner. This apartment was the perfect w
                                                          …see more

                                                          Certificate of Excellence

                                                          Price per night from

                                                          $127

                                                          Responds fast!
                                                          avg. 3 hours 34 minutes

                                                          Price per night from

                                                          $127

                                                          Distance approx 14.92 km from Wenham

                                                            4

                                                            Big Malden Room Minutes to Train (OU1)

                                                            Massachusetts / Malden

                                                            Malden room

                                                            1 2 1 night min

                                                            • 1 bedroom
                                                            • sleeps 2
                                                            • 1 night min
                                                            • Air conditioning
                                                            • Pet Friendly

                                                            Price per night from

                                                            $66

                                                            Price per night from

                                                            $66

                                                            Distance approx 19.71 km from Wenham

                                                              24

                                                              NEW! Updated 1BR Boston Condo in Central Back Bay!

                                                              Massachusetts / Boston

                                                              Boston apartment

                                                              1 3 min stay varies

                                                              • 1 bedroom
                                                              • sleeps 3
                                                              • min stay varies
                                                              • Child Friendly
                                                              • Air conditioning

                                                              Price per night from

                                                              $289

                                                              Responds fast!
                                                              avg. 13 minutes

                                                              Price per night from

                                                              $289

                                                              Distance approx 19.25 km from Wenham

                                                              (4)  

                                                                10

                                                                Boston Harbor View Luxury Suites

                                                                Massachusetts / Boston

                                                                Boston house

                                                                1 4 min stay varies

                                                                • 1 bedroom
                                                                • sleeps 4
                                                                • min stay varies
                                                                • Child Friendly
                                                                • Air conditioning
                                                                • Pet Friendly

                                                                Price per night from

                                                                $176

                                                                Price per night from

                                                                $176

                                                                Distance approx 18.94 km from Wenham

                                                                  7

                                                                  Spacious 3 bedroom near everything

                                                                  Massachusetts / Boston

                                                                  Boston apartment

                                                                  3 5 3 nights min

                                                                  • 3 bedrooms
                                                                  • sleeps 5
                                                                  • 3 nights min
                                                                  • Child Friendly
                                                                  • Air conditioning
                                                                  • Pet Friendly

                                                                  Price per night from

                                                                  $230

                                                                  Price per night from

                                                                  $230

                                                                  Distance approx 17.05 km from Wenham

                                                                  (7) Excellent 

                                                                    35

                                                                    Beautiful Ocean Front Beach Condo in Salisbury, MA

                                                                    Massachusetts / Salisbury

                                                                    Salisbury condo

                                                                    2 5 7 nights min

                                                                    • 2 bedrooms
                                                                    • sleeps 5
                                                                    • 7 nights min
                                                                    • Beach / lakeside relaxation
                                                                    • Child Friendly
                                                                    • Air conditioning

                                                                    Price per night from

                                                                    $360

                                                                    Price per night from

                                                                    $360

                                                                    Distance approx 14.16 km from Wenham

                                                                    (4) Excellent 

                                                                      46

                                                                      Directly on Long Beach Rockport MA

                                                                      Cape Ann / Rockport

                                                                      Rockport house

                                                                      4 14 min stay varies

                                                                      • 4 bedrooms
                                                                      • sleeps 14
                                                                      • min stay varies
                                                                      • Beach / lakeside relaxation
                                                                      • Nearest beach 0 mi
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $437

                                                                      Price per night from

                                                                      $437

                                                                      Distance approx 19.14 km from Wenham

                                                                        38

                                                                        1 BR AT PIER FOUR BLVD IN SOUTH BOSTON

                                                                        Massachusetts / Boston

                                                                        Boston apartment

                                                                        1 3 3 nights min

                                                                        • 1 bedroom
                                                                        • sleeps 3
                                                                        • 3 nights min
                                                                        • Swimming pool
                                                                        • Child Friendly
                                                                        • Air conditioning

                                                                        Price per night from

                                                                        $589

                                                                        Price per night from

                                                                        $589

                                                                        Distance approx 19.14 km from Wenham

                                                                          37

                                                                          2 BR AT PIER FOUR BLVD IN SOUTH BOSTON

                                                                          Massachusetts / Boston

                                                                          Boston apartment

                                                                          2 5 30 nights min

                                                                          • 2 bedrooms
                                                                          • sleeps 5
                                                                          • 30 nights min
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $824

                                                                          Price per night from

                                                                          $824

                                                                          Distance approx 18.9 km from Wenham

                                                                            32

                                                                            3 BEDROOMS AT EMERSON PLACE IN WEST END

                                                                            Massachusetts / Boston

                                                                            Boston apartment

                                                                            3 7 3 nights min

                                                                            • 3 bedrooms
                                                                            • sleeps 7
                                                                            • 3 nights min
                                                                            • Swimming pool
                                                                            • Child Friendly
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $942

                                                                            Price per night from

                                                                            $942

                                                                            Distance approx 7.25 km from Wenham Show on Map

                                                                              31

                                                                              Charming historic building from 1700's!

                                                                              Massachusetts / Marblehead

                                                                              Marblehead condo

                                                                              1 4 min stay varies

                                                                              • 1 bedroom
                                                                              • sleeps 4
                                                                              • min stay varies
                                                                              • Air conditioning
                                                                              • Pet Friendly

                                                                              Price per night from

                                                                              $106

                                                                              Price per night from

                                                                              $106