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85 Houses

    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. 29 minutes

    Price per night from

    $487

      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

      (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. 29 minutes

        Price per night from

        $458

          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

            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

              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

              $476

              Responds fast!
              avg. 1 hour 7 minutes

              Price per night from

              $476

              Great rentals within 20 miles that match your search

              Distance approx 11.47 km from Stevensville

              (1) Excellent 

                10

                Summer House

                Maryland / Rock Hall

                Rock Hall bungalow

                3 8 2 nights min

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

                Price per night from

                $327

                Price per night from

                $327

                Distance approx 11.36 km from Stevensville

                  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

                  $287

                  Responds fast!
                  avg. 3 hours 15 minutes

                  Price per night from

                  $287

                  Distance approx 14.25 km from Stevensville

                    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 14.38 km from Stevensville Show on Map

                      24

                      Shady Side House on Chesapeake Bay Near Marina!

                      Maryland / Shady Side

                      Shady Side house

                      2 5 2 nights min

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

                      Price per night from

                      $212

                      Responds fast!
                      avg. 29 minutes

                      Price per night from

                      $212

                      Distance approx 14.31 km from Stevensville

                      (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 12.44 km from Stevensville

                        (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
                          …see more

                          Price per night from

                          $338

                          Price per night from

                          $338

                          Distance approx 11.38 km from Stevensville

                          (3) Excellent 

                            12

                            Sailors Crossing

                            Maryland / Rock Hall

                            Rock Hall house

                            3 10 2 nights min

                            • 3 bedrooms
                            • sleeps 10
                            • 2 nights min
                            • Child Friendly
                            • Pet Friendly

                            Price per night from

                            $390

                            Responds fast!
                            avg. 3 hours 15 minutes

                            Price per night from

                            $390

                            Distance approx 19.23 km from Stevensville

                            (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 7.91 km from Stevensville Show on Map

                              (2) Excellent 

                                10

                                C/ean & Cozy

                                Maryland / Annapolis

                                Annapolis room

                                1 2 1 night min

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

                                Price per night from

                                $68

                                Price per night from

                                $68

                                Distance approx 18.05 km from Stevensville

                                  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 15.49 km from Stevensville

                                    21

                                    Annapolis Area Waterfront Home

                                    Maryland / Annapolis

                                    Annapolis house

                                    5 11 min stay varies

                                    • 5 bedrooms
                                    • sleeps 11
                                    • min stay varies
                                    • Beach / lakeside relaxation
                                    • Child Friendly
                                    • Air conditioning

                                    Price per night from

                                    $630

                                    Price per night from

                                    $630

                                    Distance approx 3.41 km from Stevensville Show on Map

                                    (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
                                      • Child Friendly

                                      Price per night from

                                      $859

                                      Price per night from

                                      $859

                                      Distance approx 9.7 km from Stevensville Show on Map

                                      (1) Excellent 

                                        17

                                        Excellent Location in Downtown Annapolis- walk to everything !

                                        Maryland / Annapolis

                                        Annapolis house

                                        3 7 2 nights min

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

                                        Price per night from

                                        $327

                                        Responds fast!
                                        avg. 1 hour 1 minutes

                                        Price per night from

                                        $327

                                        Distance approx 14.96 km from Stevensville Show on Map

                                        (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 17.21 km from Stevensville

                                          (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 7.91 km from Stevensville Show on Map

                                              12

                                              Clean & Spacious

                                              Maryland / Cape Saint Claire

                                              Cape Saint Claire house

                                              4 9 1 night min

                                              • 4 bedrooms
                                              • sleeps 9
                                              • 1 night min
                                              • Child Friendly
                                              • Air conditioning
                                              • Private garden

                                              Price per night from

                                              $401

                                              Price per night from

                                              $401

                                              Distance approx 14.31 km from Stevensville

                                              (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 9.69 km from Stevensville Show on Map

                                                (2) Excellent 

                                                  52

                                                  Walk to Shops/Eateries Charming Cottage. Dogs Wel.

                                                  Maryland / Annapolis

                                                  Annapolis house

                                                  3 6 min stay varies

                                                  • 3 bedrooms
                                                  • sleeps 6
                                                  • min stay varies
                                                  • Nearest beach 6 mi
                                                  • Child Friendly
                                                  • Car not necessary

                                                  Price per night from

                                                  $287

                                                  Responds fast!
                                                  avg. 27 minutes

                                                  Price per night from

                                                  $287

                                                  Distance approx 14.56 km from Stevensville Show on Map

                                                    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 12.98 km from Stevensville

                                                      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

                                                      Distance approx 18.91 km from Stevensville

                                                        15

                                                        BEULAH Residence (Bedroom 1)

                                                        Maryland / Glen Burnie

                                                        Glen Burnie guest house

                                                        1 2 3 nights min

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

                                                        Price per night from

                                                        $115

                                                        Price per night from

                                                        $115

                                                        Distance approx 17.21 km from Stevensville

                                                        (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 14.55 km from Stevensville

                                                            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 10.18 km from Stevensville Show on Map

                                                              4

                                                              Perfect Annapolis with Lots of Parking & Hot Tub

                                                              Maryland / Annapolis

                                                              Annapolis townhouse

                                                              4 10 2 nights min

                                                              • 4 bedrooms
                                                              • sleeps 10
                                                              • 2 nights min
                                                              • Child Friendly

                                                              Price per night from

                                                              $567

                                                              Price per night from

                                                              $567

                                                              Distance approx 10.11 km from Stevensville Show on Map

                                                              (3) Very Good 

                                                                30

                                                                Beautiful Murray Hill Home (Annapolis)

                                                                Maryland / Annapolis

                                                                Annapolis house

                                                                4 9 min stay varies

                                                                • 4 bedrooms
                                                                • sleeps 9
                                                                • min stay varies
                                                                • Child Friendly
                                                                • Air conditioning
                                                                • Ask about pets
                                                                “Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decor
                                                                …see more

                                                                Price per night from

                                                                $487

                                                                Price per night from

                                                                $487

                                                                Distance approx 18.91 km from Stevensville

                                                                  15

                                                                  BEULAH Residence (Bedroom 4)

                                                                  Maryland / Glen Burnie

                                                                  Glen Burnie guest house

                                                                  1 2 3 nights min

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

                                                                  Price per night from

                                                                  $115

                                                                  Price per night from

                                                                  $115

                                                                  Distance approx 16.03 km from Stevensville

                                                                    52

                                                                    Sabrina House | Sleeps 13 | Severna Park

                                                                    Maryland / Severna Park

                                                                    Severna Park house

                                                                    4 13 2 nights min

                                                                    • 4 bedrooms
                                                                    • sleeps 13
                                                                    • 2 nights min
                                                                    • Child Friendly
                                                                    • Air conditioning
                                                                    • Private garden

                                                                    Price per night from

                                                                    $228

                                                                    Price per night from

                                                                    $228

                                                                    Distance approx 11.32 km from Stevensville

                                                                      12

                                                                      Bayside Retreat

                                                                      Maryland / Rock Hall

                                                                      Rock Hall house

                                                                      3 6 min stay varies

                                                                      • 3 bedrooms
                                                                      • sleeps 6
                                                                      • min stay varies
                                                                      • Child Friendly
                                                                      • Air conditioning
                                                                      • Pet Friendly

                                                                      Price per night from

                                                                      $241

                                                                      Responds fast!
                                                                      avg. 3 hours 15 minutes

                                                                      Price per night from

                                                                      $241

                                                                      Distance approx 3.41 km from Stevensville Show on Map

                                                                      (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

                                                                        Price per night from

                                                                        $1,718

                                                                        Distance approx 5.09 km from Stevensville Show on Map

                                                                        (5) Excellent 

                                                                          17

                                                                          KI Golf House-A PAR for the Course & Mile to Beach

                                                                          Maryland / Kent Island

                                                                          Kent Island house

                                                                          4 10 min stay varies

                                                                          • 4 bedrooms
                                                                          • sleeps 10
                                                                          • min stay varies
                                                                          • Nearest beach 1 mi
                                                                          • Child Friendly
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $458

                                                                          Responds fast!
                                                                          avg. 1 hour 7 minutes

                                                                          Price per night from

                                                                          $458

                                                                          Distance approx 10.09 km from Stevensville Show on Map

                                                                          (4) Excellent 

                                                                            31

                                                                            Charming Home close to historic district

                                                                            Maryland / Annapolis

                                                                            Annapolis house

                                                                            2 6 2 nights min

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

                                                                            Price per night from

                                                                            $287

                                                                            Responds fast!
                                                                            avg. 2 hours 2 minutes

                                                                            Price per night from

                                                                            $287

                                                                            Distance approx 17.7 km from Stevensville

                                                                            (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