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54 Houses

    15

    Lakeside Private Apartment

    Talbot County / Wye Mills

    Wye Mills apartment

    1 5 1 night min

    • 1 bedroom
    • sleeps 5
    • 1 night min
    • Child Friendly
    • Air conditioning
    • Pet Friendly

    Price per night from

    $160

    Price per night from

    $160

    Great rentals within 20 miles that match your search

    Distance approx 14.94 km from Wye Mills

    (3) Very Good 

      15

      Halos'Haven Vacation Rental

      St. Michaels / McDaniel

      McDaniel house

      5 10 2 nights min

      • 5 bedrooms
      • sleeps 10
      • 2 nights min
      • Swimming pool
      • Child Friendly
      • Air conditioning

      Price per night from

      $802

      Price per night from

      $802

      Distance approx 16.07 km from Wye Mills

        8

        Bay Cottage

        Maryland / Rock Hall

        Rock Hall house

        2 5 2 nights min

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

        Price per night from

        $229

        Responds fast!
        avg. 3 hours 15 minutes

        Price per night from

        $229

        Distance approx 15.65 km from Wye Mills

          25

          Waterfront Stevensville House w/ Pier & 2 Decks!

          Kent Island / Stevensville

          Stevensville house

          5 12 min stay varies

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

          Price per night from

          $487

          Responds fast!
          avg. 19 minutes

          Price per night from

          $487

          Distance approx 13.87 km from Wye Mills

            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 21 minutes

            Price per night from

            $859

            Distance approx 18.87 km from Wye Mills

            (3) Excellent 

              7

              Cottage On Kent

              Maryland / Chestertown

              Chestertown cottage

              1 3 1 night min

              • 1 bedroom
              • sleeps 3
              • 1 night min
              • Air conditioning
              • Private garden

              Price per night from

              $224

              Price per night from

              $224

              Distance approx 18.34 km from Wye Mills

              (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 15.28 km from Wye Mills

                  9

                  Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina

                  Kent Island / Stevensville

                  Stevensville house

                  4 12 min stay varies

                  • 4 bedrooms
                  • sleeps 12
                  • min stay varies
                  • Child Friendly
                  • Air conditioning
                  • Private garden

                  Price per night from

                  $475

                  Responds fast!
                  avg. 1 hour 7 minutes

                  Price per night from

                  $475

                  Distance approx 15.44 km from Wye Mills

                    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 17.7 km from Wye Mills

                    (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 11.98 km from Wye Mills

                      (3) Very Good 

                        14

                        Retreat at a quiet, water front cottage

                        Maryland / Chestertown

                        Chestertown house

                        3 8 2 nights min

                        • 3 bedrooms
                        • sleeps 8
                        • 2 nights min
                        • Child Friendly
                        • Air conditioning
                        • Private garden
                        “A best kept secret!” I have had the pleasure of staying at Cliff Point many times. The view cannot be matched, water views more than 180 degrees, sunsets are stunning. But on top of that the house is so comfortable and charming, spacious and cozy. Ch

                        Price per night from

                        $338

                        Price per night from

                        $338

                        Distance approx 16.23 km from Wye Mills

                          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 12.9 km from Wye Mills

                            26

                            Love Point Luxury Waterfront in Stevensville

                            Kent Island / Stevensville

                            Stevensville house

                            3 10 3 nights min

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

                            Price per night from

                            $1,602

                            Price per night from

                            $1,602

                            Distance approx 13.21 km from Wye Mills

                              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 19.22 km from Wye Mills

                              (5) Excellent 

                              Certificate of Excellence

                                28

                                Cozy & Spacious Chestertown Home

                                Maryland / Chestertown

                                Chestertown house

                                4 8 2 nights min

                                • 4 bedrooms
                                • sleeps 8
                                • 2 nights min
                                • Nearest beach 8 mi
                                • Swimming pool
                                • Child Friendly

                                Certificate of Excellence

                                Price per night from

                                $287

                                Responds fast!
                                avg. 2 hours 16 minutes

                                Price per night from

                                $287

                                Distance approx 18.36 km from Wye Mills

                                  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 16.46 km from Wye Mills

                                  (1) Excellent 

                                    26

                                    Huge Stevensville House Overlooking Eastern Shore!

                                    Kent Island / Stevensville

                                    Stevensville house

                                    3 10 min stay varies

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

                                    Price per night from

                                    $458

                                    Responds fast!
                                    avg. 19 minutes

                                    Price per night from

                                    $458

                                    Distance approx 13.02 km from Wye Mills

                                      11

                                      Love Point Bay Vacation Home

                                      Kent Island / Stevensville

                                      Stevensville apartment

                                      2 6 2 nights min

                                      • 2 bedrooms
                                      • sleeps 6
                                      • 2 nights min
                                      • Child Friendly

                                      Price per night from

                                      $377

                                      Price per night from

                                      $377

                                      Distance approx 14.34 km from Wye Mills

                                      (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

                                        $413

                                        Price per night from

                                        $413

                                        Distance approx 12.43 km from Wye Mills

                                        (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 12.21 km from Wye Mills

                                            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 12.19 km from Wye Mills

                                            (1) Excellent 

                                              32

                                              KENT ISLAND-OCEAN VIEW Home for rent -4 bedrooms EASTERN SHORE sleeps 10-12

                                              Maryland / Kent Island

                                              Kent Island house

                                              4 10 2 nights min

                                              • 4 bedrooms
                                              • sleeps 10
                                              • 2 nights min
                                              • Nearest beach 5 mi
                                              • Swimming pool
                                              • Air conditioning

                                              Price per night from

                                              $1,718

                                              Responds fast!
                                              avg. 11 minutes

                                              Price per night from

                                              $1,718

                                              Distance approx 19.71 km from Wye Mills

                                                24

                                                NEW! Annapolis Home w/ Deck & Whitehall Bay Access

                                                Maryland / Cape Saint Claire

                                                Cape Saint Claire house

                                                4 8 min stay varies

                                                • 4 bedrooms
                                                • sleeps 8
                                                • min stay varies
                                                • Child Friendly
                                                • Air conditioning

                                                Price per night from

                                                $251

                                                Responds fast!
                                                avg. 19 minutes

                                                Price per night from

                                                $251

                                                Distance approx 16.38 km from Wye Mills

                                                  43

                                                  Skeet shoot in the back yard of your rental

                                                  Maryland / Rock Hall

                                                  Rock Hall house

                                                  3 5 1 night min

                                                  • 3 bedrooms
                                                  • sleeps 5
                                                  • 1 night min
                                                  • Child Friendly

                                                  Price per night from

                                                  $115

                                                  Responds fast!
                                                  avg. 2 hours 49 minutes

                                                  Price per night from

                                                  $115

                                                  Distance approx 16.05 km from Wye Mills

                                                    88

                                                    Great vacation rental located in the waterfront town of Rock Hall

                                                    Maryland / Rock Hall

                                                    Rock Hall house

                                                    4 7 1 night min

                                                    • 4 bedrooms
                                                    • sleeps 7
                                                    • 1 night min
                                                    • Child Friendly

                                                    Price per night from

                                                    $115

                                                    Responds fast!
                                                    avg. 2 hours 49 minutes

                                                    Price per night from

                                                    $115

                                                    Distance approx 18.52 km from Wye Mills

                                                      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 18.36 km from Wye Mills

                                                        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 16.16 km from Wye Mills

                                                          9

                                                          Summer House in Rock Hall

                                                          Maryland / Rock Hall

                                                          Rock Hall house

                                                          3 8 3 nights min

                                                          • 3 bedrooms
                                                          • sleeps 8
                                                          • 3 nights min
                                                          • Child Friendly
                                                          • Car not necessary
                                                          • Air conditioning

                                                          Price per night from

                                                          $229

                                                          Responds fast!
                                                          avg. 3 hours 15 minutes

                                                          Price per night from

                                                          $229

                                                          Distance approx 9.45 km from Wye Mills

                                                          (15) Excellent 

                                                            35

                                                            Luxury vacation condominum with private beach

                                                            Kent Island / Chester

                                                            Chester house

                                                            4 10 2 nights min

                                                            • 4 bedrooms
                                                            • sleeps 10
                                                            • 2 nights min
                                                            • Beach / lakeside relaxation
                                                            • Nearest beach 0.2 mi
                                                            • Child Friendly

                                                            Price per night from

                                                            $440

                                                            Price per night from

                                                            $440

                                                            Distance approx 18.25 km from Wye Mills

                                                            (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

                                                              $430

                                                              Price per night from

                                                              $430

                                                              Distance approx 16.31 km from Wye Mills

                                                                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

                                                                Distance approx 13.72 km from Wye Mills

                                                                  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 19.22 km from Wye Mills

                                                                  (3) Excellent 

                                                                    17

                                                                    Belle Rose Cottage at Victory Farm (Pet Friendly!)

                                                                    Maryland / Chestertown

                                                                    Chestertown house

                                                                    1 3 1 night min

                                                                    • 1 bedroom
                                                                    • sleeps 3
                                                                    • 1 night min
                                                                    • Child Friendly
                                                                    • Air conditioning
                                                                    • Pet Friendly

                                                                    Price per night from

                                                                    $155

                                                                    Price per night from

                                                                    $155

                                                                    Distance approx 14.5 km from Wye Mills

                                                                      17

                                                                      Serene Waterfront Apartment on Kent Island

                                                                      Kent Island / Stevensville

                                                                      Stevensville apartment

                                                                      1 2 min stay varies

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

                                                                      Price per night from

                                                                      $172

                                                                      Price per night from

                                                                      $172

                                                                      Distance approx 2.38 km from Wye Mills Show on Map

                                                                        13

                                                                        Luxury Apartment with Private Entrance

                                                                        Maryland / Centreville

                                                                        Centreville apartment

                                                                        1 3 1 night min

                                                                        • 1 bedroom
                                                                        • sleeps 3
                                                                        • 1 night min
                                                                        • Air conditioning
                                                                        • Private garden

                                                                        Price per night from

                                                                        $134

                                                                        Price per night from

                                                                        $134

                                                                        Distance approx 11.86 km from Wye Mills

                                                                          12

                                                                          Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!

                                                                          Kent Island / Chester

                                                                          Chester house

                                                                          4 12 2 nights min

                                                                          • 4 bedrooms
                                                                          • sleeps 12
                                                                          • 2 nights min
                                                                          • Child Friendly
                                                                          • Air conditioning
                                                                          • Private garden

                                                                          Price per night from

                                                                          $401

                                                                          Price per night from

                                                                          $401

                                                                          Distance approx 12.19 km from Wye Mills

                                                                          (1) Excellent 

                                                                            32

                                                                            DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12

                                                                            Kent Island / Chester

                                                                            Chester house

                                                                            4 10 2 nights min

                                                                            • 4 bedrooms
                                                                            • sleeps 10
                                                                            • 2 nights min
                                                                            • Nearest beach 127 mi
                                                                            • Swimming pool
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $1,374

                                                                            Responds fast!
                                                                            avg. 11 minutes

                                                                            Price per night from

                                                                            $1,374

                                                                            Distance approx 13.15 km from Wye Mills

                                                                            (12) 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

                                                                              Price per night from

                                                                              $401

                                                                              Responds fast!
                                                                              avg. 2 hours 48 minutes

                                                                              Price per night from

                                                                              $401