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80 Houses

    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. 47 minutes

      Price per night from

      $458

        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. 9 minutes

        Price per night from

        $487

          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

          (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

            (14) Excellent 

              19

              Love Point Waterfront

              Maryland / Kent Island

              Kent Island house

              3 12 3 nights min

              • 3 bedrooms
              • sleeps 12
              • 3 nights min
              • Beach / lakeside relaxation
              • Nearest beach 5 mi
              • Child Friendly
              “Love Point Retreat” I stayed at Paula's property 3 times so far. We stayed once in October 2014 and twice in April 2015. Here is how I would break it up: Owner: Paula is very nice, accommodating and extremely responsive. She was easy to deal with, ans
              …see more

              Price per night from

              $287

              Price per night from

              $287

                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

                (3) Excellent 

                  21

                  Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)

                  Kent Island / Chester

                  Chester house

                  4 8 min stay varies

                  • 4 bedrooms
                  • sleeps 8
                  • min stay varies
                  • Beach / lakeside relaxation
                  • Nearest beach 14 mi
                  • Child Friendly
                  “Unbelievable value” We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants,
                  …see more

                  Price per night from

                  $327

                  Responds fast!
                  avg. 3 hours 2 minutes

                  Price per night from

                  $327

                    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

                    (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

                      (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

                        (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

                            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 9.65 km from Kent Island Show on Map

                            (3) Very Good 

                              36

                              Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

                              Talbot County / Wittman

                              Wittman log cabin

                              5 10 min stay varies

                              • 5 bedrooms
                              • sleeps 10
                              • min stay varies
                              • Beach / lakeside relaxation
                              • Nearest beach 6 mi
                              • Swimming pool

                              Price per night from

                              $1,117

                              Price per night from

                              $1,117

                              Distance approx 14.67 km from Kent Island Show on Map

                              (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 7.43 km from Kent Island Show on Map

                                  26

                                  Annapolis Crows Nest Cottage: Chesapeake Bay View

                                  Maryland / Annapolis

                                  Annapolis villa

                                  5 20 min stay varies

                                  • 5 bedrooms
                                  • sleeps 20
                                  • min stay varies
                                  • Beach / lakeside relaxation
                                  • Nearest beach 0.2 mi
                                  • Child Friendly

                                  Price per night from

                                  $796

                                  Price per night from

                                  $796

                                  Distance approx 18.47 km from Kent Island

                                    11

                                    Panoramic Views of Herrington Harbour on the Bay.

                                    Calvert County / North Beach

                                    North Beach house

                                    3 8 1 night min

                                    • 3 bedrooms
                                    • sleeps 8
                                    • 1 night min
                                    • Child Friendly
                                    • Air conditioning
                                    • Pet Friendly

                                    Price per night from

                                    $573

                                    Price per night from

                                    $573

                                    Distance approx 18.08 km from Kent Island

                                      24

                                      Contemporary Pasadena Apt w/Fireplace -Near River!

                                      Maryland / Pasadena

                                      Pasadena apartment

                                      2 4 min stay varies

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

                                      Price per night from

                                      $101

                                      Responds fast!
                                      avg. 9 minutes

                                      Price per night from

                                      $101

                                      Distance approx 14.41 km from Kent Island

                                        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 19.1 km from Kent Island

                                          9

                                          Renovated Luxury Waterview House

                                          Calvert County / North Beach

                                          North Beach house

                                          3 6 2 nights min

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

                                          Price per night from

                                          $344

                                          Price per night from

                                          $344

                                          Distance approx 14.56 km from Kent Island Show on Map

                                          (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 16.17 km from Kent Island

                                              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 14.23 km from Kent Island

                                              (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 11.85 km from Kent Island Show on Map

                                                (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 10.05 km from Kent Island Show on Map

                                                  (6) Excellent 

                                                    19

                                                    Charming and Spacious Annapolis Victorian

                                                    Maryland / Annapolis

                                                    Annapolis house

                                                    6 12 min stay varies

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

                                                    Price per night from

                                                    $859

                                                    Responds fast!
                                                    avg. 1 hour 27 minutes

                                                    Price per night from

                                                    $859

                                                    Distance approx 14.04 km from Kent Island

                                                    (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 11.34 km from Kent Island Show on Map

                                                        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 14.23 km from Kent Island

                                                        (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 14.97 km from Kent Island

                                                            29

                                                            Custom Annapolis Home w/ Private Pool & Hot Tub!

                                                            Maryland / Riva

                                                            Riva house

                                                            3 8 min stay varies

                                                            • 3 bedrooms
                                                            • sleeps 8
                                                            • min stay varies
                                                            • Swimming pool
                                                            • Child Friendly
                                                            • Air conditioning

                                                            Price per night from

                                                            $331

                                                            Responds fast!
                                                            avg. 10 minutes

                                                            Price per night from

                                                            $331

                                                            Distance approx 9.57 km from Kent Island 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 12.77 km from Kent Island Show on Map

                                                                4

                                                                Lochhaven house for rent

                                                                Maryland / Edgewater

                                                                Edgewater house

                                                                3 2 7 nights min

                                                                • 3 bedrooms
                                                                • sleeps 2
                                                                • 7 nights min
                                                                • Air conditioning
                                                                • Private garden

                                                                Price per night from

                                                                $115

                                                                Price per night from

                                                                $115

                                                                Distance approx 17.05 km from Kent Island

                                                                  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 14.74 km from Kent Island Show on Map

                                                                    53

                                                                    2 Twin bed rental located in a 4 bedroom great vacation house in the waterfront

                                                                    Maryland / Rock Hall

                                                                    Rock Hall house

                                                                    1 3 1 night min

                                                                    • 1 bedroom
                                                                    • sleeps 3
                                                                    • 1 night min
                                                                    • Nearest beach 2 mi
                                                                    • Child Friendly
                                                                    • Air conditioning

                                                                    Price per night from

                                                                    $46

                                                                    Responds fast!
                                                                    avg. 2 hours 10 minutes

                                                                    Price per night from

                                                                    $46

                                                                    Distance approx 6.81 km from Kent Island Show on Map

                                                                      39

                                                                      Annapolis Home w/ Bay Views - Near Naval Academy!

                                                                      Maryland / Annapolis

                                                                      Annapolis house

                                                                      5 11 min stay varies

                                                                      • 5 bedrooms
                                                                      • sleeps 11
                                                                      • min stay varies
                                                                      • Swimming pool
                                                                      • Child Friendly
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $819

                                                                      Responds fast!
                                                                      avg. 9 minutes

                                                                      Price per night from

                                                                      $819

                                                                      Distance approx 9.18 km from Kent Island Show on Map

                                                                      (1) Excellent 

                                                                        18

                                                                        Stunning Home in the Heart of Downtown Annapolis

                                                                        Maryland / Annapolis

                                                                        Annapolis house

                                                                        3 11 2 nights min

                                                                        • 3 bedrooms
                                                                        • sleeps 11
                                                                        • 2 nights min
                                                                        • Ask about children
                                                                        • Air conditioning
                                                                        • Private garden

                                                                        Price per night from

                                                                        $796

                                                                        Price per night from

                                                                        $796

                                                                        Distance approx 14.51 km from Kent Island Show on Map

                                                                          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 15.39 km from Kent Island

                                                                          (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 9.68 km from Kent Island 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