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39 Houses

    29

    NEW! Colonial Home in Cambridge w/Wraparound Porch

    Maryland / Cambridge

    Cambridge house

    3 7 min stay varies

    • 3 bedrooms
    • sleeps 7
    • min stay varies
    • Child Friendly
    • Air conditioning

    Price per night from

    $264

    Responds fast!
    avg. 36 minutes

    Price per night from

    $264

      16

      Choptank River View House

      Maryland / Cambridge

      Cambridge house

      6 14 3 nights min

      • 6 bedrooms
      • sleeps 14
      • 3 nights min
      • Beach / lakeside relaxation
      • Nearest beach 0 mi
      • Air conditioning

      Price per night from

      $1,141

      Price per night from

      $1,141

        8

        6 Bdrm, 3.5 Bath, Cambridge Md Vacation Home

        Maryland / Cambridge

        Cambridge house

        6 12 3 nights min

        • 6 bedrooms
        • sleeps 12
        • 3 nights min
        • Child Friendly
        • Air conditioning
        • Pet Friendly

        Price per night from

        $995

        Price per night from

        $995

        (12) Very Good 

          31

          Stunning, Newer Chesapeake Waterfront Estate, Pool - 6/7 Bedrms 5 Baths

          Maryland / Cambridge

          Cambridge house

          6 20 min stay varies

          • 6 bedrooms
          • sleeps 20
          • min stay varies
          • Beach / lakeside relaxation
          • Nearest beach 0.1 mi
          • Swimming pool
          “Outstanding Vacation Rental” Our extended family (22 people - 13A/9K) had a great week at Saddle Beach. The house was beautiful and in very good condition. The option of being in the pool or the river during the day was wonderful. The house was cle
          …see more

          Price per night from

          $572

          Price per night from

          $572

          (15) Excellent 

            35

            Year Round Estate on Bay / Fam. Reunions / Slps 28

            Maryland / Cambridge

            Cambridge house

            7 28 min stay varies

            • 7 bedrooms
            • sleeps 28
            • min stay varies
            • Beach / lakeside relaxation
            • Swimming pool
            • Ask about children
            “Unbelievable Home in an Unbelievable Setting!!!” Our family cant thank you enough for the memories made at captains quarters this summer. This was the first time getting away with the entire family (kids grandkids, grand parents, etc) and it was prop
            …see more

            Price per night from

            $1,000

            Price per night from

            $1,000

            (10) Excellent 

              50

              Cottage at Heron Cove, Chesapeake Bay, Cambridge

              Maryland / Cambridge

              Cambridge cottage

              3 5 min stay varies

              • 3 bedrooms
              • sleeps 5
              • min stay varies
              • Beach / lakeside relaxation
              • Child Friendly
              • Air conditioning

              Price per night from

              $172

              Price per night from

              $172

              Great rentals within 20 miles that match your search

              Distance approx 2.55 km from Cambridge Show on Map

                42

                Waterfront Room Rentals 2 with Private Beach

                Talbot County / Trappe

                Trappe room

                1 2 min stay varies

                • 1 bedroom
                • sleeps 2
                • min stay varies
                • Child Friendly
                • Air conditioning
                • Pet Friendly

                Price per night from

                $115

                Responds fast!
                avg. 1 hour 34 minutes

                Price per night from

                $115

                Distance approx 2.55 km from Cambridge Show on Map

                (1) Very Good 

                  34

                  Waterfront Room Rentals 1 with Private Beach

                  Talbot County / Trappe

                  Trappe room

                  1 2 min stay varies

                  • 1 bedroom
                  • sleeps 2
                  • min stay varies
                  • Child Friendly
                  • Air conditioning
                  • Pet Friendly

                  Price per night from

                  $149

                  Responds fast!
                  avg. 1 hour 34 minutes

                  Price per night from

                  $149

                  Distance approx 2.56 km from Cambridge Show on Map

                  (5) Average 

                    55

                    Waterfront Vacation Home with Private Beach

                    Talbot County / Trappe

                    Trappe house

                    3 6 2 nights min

                    • 3 bedrooms
                    • sleeps 6
                    • 2 nights min
                    • Beach / lakeside relaxation
                    • Nearest beach 97 mi
                    • Child Friendly

                    Price per night from

                    $387

                    Responds fast!
                    avg. 1 hour 34 minutes

                    Price per night from

                    $387

                    Distance approx 2.55 km from Cambridge Show on Map

                      44

                      Waterfront Room Rentals 3 with Private Beach

                      Talbot County / Trappe

                      Trappe room

                      1 2 min stay varies

                      • 1 bedroom
                      • sleeps 2
                      • min stay varies
                      • Child Friendly
                      • Air conditioning
                      • Pet Friendly

                      Price per night from

                      $115

                      Responds fast!
                      avg. 1 hour 34 minutes

                      Price per night from

                      $115

                      Distance approx 15.55 km from Cambridge

                        37

                        St. Michaels Waterfront Retreat with pier, pool, kayaks, gas fire pit and bikes

                        Talbot County / Royal Oak

                        Royal Oak house

                        5 10 min stay varies

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

                        Price per night from

                        $572

                        Price per night from

                        $572

                        Distance approx 17.22 km from Cambridge

                        (11) Very Good 

                          30

                          Large Historic Thomas Harrison House on Harbor in St. Michaels Town

                          Talbot County / St. Michaels

                          St. Michaels house

                          7 9 min stay varies

                          • 7 bedrooms
                          • sleeps 9
                          • min stay varies
                          • Beach / lakeside relaxation
                          • Child Friendly
                          • Air conditioning
                          “Perfect in every way!” I stayed at the Thomas Harrison house a few weeks ago and all I can say is..."if you are planning on coming to St. Michael's you need to stay at this house." This house is perfect in every way. It has all the accommodations that
                          …see more

                          Price per night from

                          $401

                          Responds fast!
                          avg. 2 hours 48 minutes

                          Price per night from

                          $401

                          Distance approx 15.82 km from Cambridge

                          (1) Excellent 

                            18

                            St. Michaels Waterfront Home W/Dock for 2 boats

                            Talbot County / Neavitt

                            Neavitt house

                            2 5 min stay varies

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

                            Price per night from

                            $257

                            Price per night from

                            $257

                            Distance approx 18.53 km from Cambridge

                            (2) Very Good 

                              35

                              Chesapeake Bay Waterfront on Hoopers Island with Private Beach

                              Maryland / Fishing Creek

                              Fishing Creek house

                              5 12 min stay varies

                              • 5 bedrooms
                              • sleeps 12
                              • min stay varies
                              • Child Friendly
                              • Air conditioning
                              • Pet Friendly

                              Price per night from

                              $229

                              Price per night from

                              $229

                              Distance approx 17.27 km from Cambridge

                              (24) Excellent 

                                27

                                Location Location! St Michaels-- In Town Cottage!

                                Talbot County / St. Michaels

                                St. Michaels house

                                2 5 min stay varies

                                • 2 bedrooms
                                • sleeps 5
                                • min stay varies
                                • Beach / lakeside relaxation
                                • Child Friendly
                                • Car not necessary

                                Price per night from

                                $206

                                Responds fast!
                                avg. 2 hours 48 minutes

                                Price per night from

                                $206

                                Distance approx 15.79 km from Cambridge

                                  28

                                  St. Michaels Area Cottage - Walk to Water & Marina

                                  Talbot County / Neavitt

                                  Neavitt house

                                  2 4 2 nights min

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

                                  Price per night from

                                  $212

                                  Responds fast!
                                  avg. 36 minutes

                                  Price per night from

                                  $212

                                  Distance approx 16.97 km from Cambridge

                                  (2) Excellent 

                                    18

                                    Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX

                                    Talbot County / St. Michaels

                                    St. Michaels house

                                    1 6 2 nights min

                                    • 1 bedroom
                                    • sleeps 6
                                    • 2 nights min
                                    • Child Friendly
                                    • Air conditioning
                                    • Private garden

                                    Price per night from

                                    $263

                                    Price per night from

                                    $263

                                    Distance approx 17.25 km from Cambridge

                                    (13) Excellent 

                                      24

                                      Premier Cottage in St. Michaels- In Town Location!

                                      Talbot County / St. Michaels

                                      St. Michaels house

                                      2 5 min stay varies

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

                                      Price per night from

                                      $207

                                      Responds fast!
                                      avg. 2 hours 48 minutes

                                      Price per night from

                                      $207

                                      Distance approx 14.54 km from Cambridge

                                        18

                                        Historic Waterfront Property with Wi-Fi and Dock

                                        Talbot County / St. Michaels

                                        St. Michaels house

                                        3 8 2 nights min

                                        • 3 bedrooms
                                        • sleeps 8
                                        • 2 nights min
                                        • Beach / lakeside relaxation
                                        • Child Friendly
                                        • Air conditioning

                                        Price per night from

                                        $879

                                        Responds fast!
                                        avg. 3 hours 23 minutes

                                        Price per night from

                                        $879

                                        Distance approx 17.27 km from Cambridge

                                        (7) Very Good 

                                          23

                                          Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!

                                          Talbot County / St. Michaels

                                          St. Michaels cottage

                                          2 5 min stay varies

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

                                          Price per night from

                                          $217

                                          Responds fast!
                                          avg. 2 hours 48 minutes

                                          Price per night from

                                          $217

                                          Distance approx 16.16 km from Cambridge

                                            8

                                            Cottage 1a at Grandview Pleasure Point

                                            Talbot County / Bozman

                                            Bozman house

                                            1 4 2 nights min

                                            • 1 bedroom
                                            • sleeps 4
                                            • 2 nights min
                                            • Swimming pool
                                            • Ask about children
                                            • Ask about pets

                                            Price per night from

                                            $281

                                            Price per night from

                                            $281

                                            Distance approx 16.39 km from Cambridge

                                            (1) Excellent 

                                              9

                                              Cottage 2 at Grandview Pleasure Point

                                              Talbot County / Bozman

                                              Bozman house

                                              2 6 2 nights min

                                              • 2 bedrooms
                                              • sleeps 6
                                              • 2 nights min
                                              • Beach / lakeside relaxation
                                              • Swimming pool
                                              • Child Friendly

                                              Price per night from

                                              $441

                                              Price per night from

                                              $441

                                              Distance approx 19.01 km from Cambridge

                                              (3) Excellent 

                                                24

                                                Best sunrise in St. Michaels....Broadview Bay House

                                                Talbot County / St. Michaels

                                                St. Michaels house

                                                6 12 min stay varies

                                                • 6 bedrooms
                                                • sleeps 12
                                                • min stay varies
                                                • Swimming pool
                                                • Child Friendly
                                                • Air conditioning

                                                Price per night from

                                                $598

                                                Price per night from

                                                $598

                                                Distance approx 16.16 km from Cambridge

                                                  6

                                                  Cottage 1b at Grandview Pleasure Point

                                                  Talbot County / Bozman

                                                  Bozman cottage

                                                  1 2 7 nights min

                                                  • 1 bedroom
                                                  • sleeps 2
                                                  • 7 nights min
                                                  • Swimming pool
                                                  • Ask about children
                                                  • Air conditioning

                                                  Price per night from

                                                  $281

                                                  Price per night from

                                                  $281

                                                  Distance approx 18.8 km from Cambridge

                                                  (4) Excellent 

                                                    38

                                                    Hoopers Island Studio, 360 Degrees WATER VIEWS

                                                    Maryland / Fishing Creek

                                                    Fishing Creek apartment

                                                    1 3 min stay varies

                                                    • 1 bedroom
                                                    • sleeps 3
                                                    • min stay varies
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 32 mi
                                                    • Ask about children
                                                    “What a fantastic stay!” As soon as we stepped out of our car, we felt like we hit the jackpot. The views in front and in back of the house are breathtaking, with water stretching to the horizons. Inside the house, we found all that we could need and
                                                    …see more

                                                    Price per night from

                                                    $183

                                                    Responds fast!
                                                    avg. 1 hour 25 minutes

                                                    Price per night from

                                                    $183

                                                    Distance approx 17.22 km from Cambridge

                                                    (3) Very Good 

                                                      25

                                                      Waterview Cottage In St. Michaels!

                                                      Talbot County / St. Michaels

                                                      St. Michaels cottage

                                                      2 5 min stay varies

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

                                                      Price per night from

                                                      $218

                                                      Responds fast!
                                                      avg. 2 hours 48 minutes

                                                      Price per night from

                                                      $218

                                                      Distance approx 16.58 km from Cambridge

                                                      (5) Excellent 

                                                        22

                                                        Sandy Pines: Enjoy Harris Creek w/Pool and Boats

                                                        Talbot County / St. Michaels

                                                        St. Michaels house

                                                        4 10 min stay varies

                                                        • 4 bedrooms
                                                        • sleeps 10
                                                        • min stay varies
                                                        • Beach / lakeside relaxation
                                                        • Swimming pool
                                                        • Child Friendly

                                                        Price per night from

                                                        $440

                                                        Price per night from

                                                        $440

                                                        Distance approx 14.11 km from Cambridge

                                                          15

                                                          Tranquil Easton Waterfront Property

                                                          Talbot County / Easton

                                                          Easton house

                                                          3 6 3 nights min

                                                          • 3 bedrooms
                                                          • sleeps 6
                                                          • 3 nights min
                                                          • Beach / lakeside relaxation
                                                          • Swimming pool
                                                          • Child Friendly

                                                          Price per night from

                                                          $685

                                                          Price per night from

                                                          $685

                                                          Distance approx 17.77 km from Cambridge

                                                            12

                                                            Harris Cove Cottages LLC

                                                            Talbot County / St. Michaels

                                                            St. Michaels cottage

                                                            1 4 1 night min

                                                            • 1 bedroom
                                                            • sleeps 4
                                                            • 1 night min
                                                            • Child Friendly
                                                            • Air conditioning

                                                            Price per night from

                                                            $229

                                                            Price per night from

                                                            $229

                                                            Distance approx 19.04 km from Cambridge

                                                              9

                                                              Eastern Shore Waterfront Home, Ready for Spring and Summer!

                                                              Maryland / Fishing Creek

                                                              Fishing Creek house

                                                              3 10 3 nights min

                                                              • 3 bedrooms
                                                              • sleeps 10
                                                              • 3 nights min
                                                              • Beach / lakeside relaxation
                                                              • Child Friendly
                                                              • Air conditioning

                                                              Price per night from

                                                              $258

                                                              Price per night from

                                                              $258

                                                              Distance approx 17.76 km from Cambridge

                                                                14

                                                                Halo's Haven Guest Quarters

                                                                Talbot County / St. Michaels

                                                                St. Michaels house

                                                                3 6 1 night min

                                                                • 3 bedrooms
                                                                • sleeps 6
                                                                • 1 night min
                                                                • Child Friendly
                                                                • Air conditioning
                                                                • Private garden

                                                                Price per night from

                                                                $373

                                                                Price per night from

                                                                $373

                                                                Distance approx 16.39 km from Cambridge

                                                                (13) Excellent 

                                                                  34

                                                                  Main House at Grandview at Pleasure Point

                                                                  Talbot County / Bozman

                                                                  Bozman house

                                                                  5 13 7 nights min

                                                                  • 5 bedrooms
                                                                  • sleeps 13
                                                                  • 7 nights min
                                                                  • Beach / lakeside relaxation
                                                                  • Nearest beach 15 mi
                                                                  • Swimming pool
                                                                  “5 out of 5” I spent a long weekend at the main house, and it was easily the best weekend of the summer! The location is phenomenal. The house sits on large stretch of beautiful waterfront property. The views from the piers and the pool are exquisite.
                                                                  …see more

                                                                  Price per night from

                                                                  $788

                                                                  Price per night from

                                                                  $788

                                                                  Distance approx 16.97 km from Cambridge

                                                                    7

                                                                    St. Michael's Premier in Town Summer Cottage!

                                                                    Talbot County / St. Michaels

                                                                    St. Michaels house

                                                                    2 4 2 nights min

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

                                                                    Price per night from

                                                                    $326

                                                                    Price per night from

                                                                    $326

                                                                    Distance approx 7.78 km from Cambridge Show on Map

                                                                      17

                                                                      Deerpond Carriage House

                                                                      Maryland / Woolford

                                                                      Woolford guest house

                                                                      1 2 3 nights min

                                                                      • 1 bedroom
                                                                      • sleeps 2
                                                                      • 3 nights min
                                                                      • Swimming pool
                                                                      • Air conditioning
                                                                      • Private garden

                                                                      Price per night from

                                                                      $207

                                                                      Price per night from

                                                                      $207

                                                                      Distance approx 18.08 km from Cambridge

                                                                      (1) Average 

                                                                        38

                                                                        St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds

                                                                        Talbot County / St. Michaels

                                                                        St. Michaels villa

                                                                        6 12 2 nights min

                                                                        • 6 bedrooms
                                                                        • sleeps 12
                                                                        • 2 nights min
                                                                        • Beach / lakeside relaxation
                                                                        • Nearest beach 7 mi
                                                                        • Swimming pool

                                                                        Price per night from

                                                                        $1,145

                                                                        Responds fast!
                                                                        avg. 3 hours 35 minutes

                                                                        Price per night from

                                                                        $1,145

                                                                        Distance approx 13.78 km from Cambridge

                                                                        (10) Excellent 

                                                                          24

                                                                          RESTORED WATERFRONT COTTAGE

                                                                          Talbot County / Royal Oak

                                                                          Royal Oak cottage

                                                                          3 6 2 nights min

                                                                          • 3 bedrooms
                                                                          • sleeps 6
                                                                          • 2 nights min
                                                                          • Beach / lakeside relaxation
                                                                          • Child Friendly
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $344

                                                                          Price per night from

                                                                          $344

                                                                          Distance approx 14.66 km from Cambridge

                                                                            20

                                                                            Maryland’s Eastern Shore Welcomes You

                                                                            Maryland / Preston

                                                                            Preston house

                                                                            1 2 1 night min

                                                                            • 1 bedroom
                                                                            • sleeps 2
                                                                            • 1 night min
                                                                            • Nearest beach 50 mi
                                                                            • Swimming pool
                                                                            • Child Friendly

                                                                            Price per night from

                                                                            $100

                                                                            Price per night from

                                                                            $100

                                                                            Distance approx 14.63 km from Cambridge

                                                                              23

                                                                              EASTERN SHORE MARYLAND WELCOMES YOU

                                                                              Maryland / Preston

                                                                              Preston house

                                                                              1 2 1 night min

                                                                              • 1 bedroom
                                                                              • sleeps 2
                                                                              • 1 night min
                                                                              • Swimming pool
                                                                              • Child Friendly
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $86

                                                                              Price per night from

                                                                              $86