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41 Houses

    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

    Great rentals within 20 miles that match your search

    Distance approx 9.48 km from Woolford

      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 9.49 km from Woolford

      (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

        $378

        Responds fast!
        avg. 1 hour 34 minutes

        Price per night from

        $378

        Distance approx 13.6 km from Woolford

        (4) Excellent 

          20

          Best kept secret by the bay (Entire House)

          Maryland / Fishing Creek

          Fishing Creek house

          3 4 3 nights min

          • 3 bedrooms
          • sleeps 4
          • 3 nights min
          • Air conditioning
          • Private garden

          Price per night from

          $194

          Responds fast!
          avg. 3 hours 10 minutes

          Price per night from

          $194

          Distance approx 9.48 km from Woolford

          (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 7.67 km from Woolford Show on Map

              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

              $1,145

              Price per night from

              $1,145

              Distance approx 7.42 km from Woolford Show on Map

                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. 29 minutes

                Price per night from

                $264

                Distance approx 9.48 km from Woolford

                  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 19.42 km from Woolford

                    24

                    Chesapeake Beach Apt. Walk to Bay, Beach & Marina!

                    Calvert County / Chesapeake Beach

                    Chesapeake Beach apartment

                    1 4 min stay varies

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

                    Price per night from

                    $81

                    Responds fast!
                    avg. 47 minutes

                    Price per night from

                    $81

                    Distance approx 15.29 km from Woolford

                    (1) Excellent 

                      24

                      New! Beachfront 4BR St. Leonard Cottage w/ Deck!

                      Calvert County / St. Leonard

                      Saint Leonard cottage

                      4 8 2 nights min

                      • 4 bedrooms
                      • sleeps 8
                      • 2 nights min
                      • Child Friendly
                      • Air conditioning

                      Price per night from

                      $184

                      Responds fast!
                      avg. 47 minutes

                      Price per night from

                      $184

                      Distance approx 13.04 km from Woolford

                      (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 18.57 km from Woolford

                          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 6.59 km from Woolford Show on Map

                            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

                            Distance approx 19.18 km from Woolford

                            (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 19.06 km from Woolford

                              (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 15.6 km from Woolford

                                  10

                                  Harbor Cottage at the Chesapeake Bay

                                  Calvert County / St. Leonard

                                  Saint Leonard cottage

                                  2 6 3 nights min

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

                                  Price per night from

                                  $298

                                  Price per night from

                                  $298

                                  Distance approx 15.76 km from Woolford

                                    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. 29 minutes

                                    Price per night from

                                    $212

                                    Distance approx 17.11 km from Woolford

                                      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

                                      $859

                                      Responds fast!
                                      avg. 3 hours 23 minutes

                                      Price per night from

                                      $859

                                      Distance approx 16.14 km from Woolford

                                        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 19.21 km from Woolford

                                        (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

                                          $207

                                          Responds fast!
                                          avg. 2 hours 48 minutes

                                          Price per night from

                                          $207

                                          Distance approx 19.19 km from Woolford

                                          (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 17.98 km from Woolford

                                              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

                                              $687

                                              Price per night from

                                              $687

                                              Distance approx 15.98 km from Woolford

                                                10

                                                Business or Leisure?

                                                Calvert County / Lusby

                                                Lusby guest house

                                                1 4 2 nights min

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

                                                Price per night from

                                                $75

                                                Responds fast!
                                                avg. 3 hours 20 minutes

                                                Price per night from

                                                $75

                                                Distance approx 18.93 km from Woolford

                                                (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

                                                  $600

                                                  Price per night from

                                                  $600

                                                  Distance approx 16.34 km from Woolford

                                                  (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

                                                    $442

                                                    Price per night from

                                                    $442

                                                    Distance approx 13.37 km from Woolford

                                                    (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

                                                      $184

                                                      Responds fast!
                                                      avg. 1 hour 25 minutes

                                                      Price per night from

                                                      $184

                                                      Distance approx 2.22 km from Woolford Show on Map

                                                      (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

                                                        Distance approx 16.14 km from Woolford

                                                          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 19.17 km from Woolford

                                                          (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 19.35 km from Woolford

                                                              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 18.69 km from Woolford

                                                                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 17.13 km from Woolford

                                                                  24

                                                                  NEW! Historic Hoopersville Home on Chesapeake Bay!

                                                                  Maryland / Fishing Creek

                                                                  Fishing Creek house

                                                                  7 17 min stay varies

                                                                  • 7 bedrooms
                                                                  • sleeps 17
                                                                  • min stay varies
                                                                  • Child Friendly
                                                                  • Air conditioning
                                                                  • Pet Friendly

                                                                  Price per night from

                                                                  $338

                                                                  Responds fast!
                                                                  avg. 29 minutes

                                                                  Price per night from

                                                                  $338

                                                                  Distance approx 13.68 km from Woolford

                                                                    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 16.34 km from Woolford

                                                                    (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

                                                                      $790

                                                                      Price per night from

                                                                      $790

                                                                      Distance approx 18.97 km from Woolford

                                                                        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

                                                                        $327

                                                                        Price per night from

                                                                        $327

                                                                        Distance approx 16.46 km from Woolford

                                                                        (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 2.67 km from Woolford Show on Map

                                                                          (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

                                                                            Distance approx 4.97 km from Woolford Show on Map

                                                                            (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

                                                                              $168

                                                                              Price per night from

                                                                              $168