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41 Houses

    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

    Great rentals within 20 miles that match your search

    Distance approx 11.62 km from Centreville

    (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 19.3 km from Centreville

        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 11.46 km from Centreville

        (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 19.34 km from Centreville

            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

            Distance approx 12.7 km from Centreville

              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 11.41 km from Centreville

                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 11.99 km from Centreville

                (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 5 mi
                  • Swimming pool
                  • Child Friendly

                  Certificate of Excellence

                  Price per night from

                  $287

                  Responds fast!
                  avg. 2 hours 21 minutes

                  Price per night from

                  $287

                  Distance approx 10.19 km from Centreville

                  (4) Very Good 

                    11

                    Chester River House with Views

                    Maryland / Chestertown

                    Chestertown house

                    3 7 2 nights min

                    • 3 bedrooms
                    • sleeps 7
                    • 2 nights min
                    • Child Friendly

                    Price per night from

                    $178

                    Responds fast!
                    avg. 2 hours 41 minutes

                    Price per night from

                    $178

                    Distance approx 19.74 km from Centreville

                    (2) Excellent 

                      18

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

                      Talbot County / St. Michaels

                      St. Michaels house

                      1 6 2 nights min

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

                      Price per night from

                      $263

                      Price per night from

                      $263

                      Distance approx 19.83 km from Centreville

                      (11) Very Good 

                        30

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

                        Talbot County / St. Michaels

                        St. Michaels house

                        7 9 min stay varies

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

                        Price per night from

                        $401

                        Responds fast!
                        avg. 2 hours 48 minutes

                        Price per night from

                        $401

                        Distance approx 19.43 km from Centreville

                        (2) Very Good 

                          39

                          Big BD in Civil War House starting at 55$/night

                          Maryland / Still Pond

                          Still Pond house

                          1 3 1 night min

                          • 1 bedroom
                          • sleeps 3
                          • 1 night min
                          • Nearest beach 5 mi
                          • Child Friendly
                          • Air conditioning

                          Price per night from

                          $63

                          Responds fast!
                          avg. 2 hours 10 minutes

                          Price per night from

                          $63

                          Distance approx 19.82 km from Centreville

                          (24) Excellent 

                            27

                            Location Location! St Michaels-- In Town Cottage!

                            Talbot County / St. Michaels

                            St. Michaels house

                            2 5 min stay varies

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

                            Price per night from

                            $207

                            Responds fast!
                            avg. 2 hours 48 minutes

                            Price per night from

                            $207

                            Distance approx 19.83 km from Centreville

                            (7) Very Good 

                              23

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

                              Talbot County / St. Michaels

                              St. Michaels cottage

                              2 5 min stay varies

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

                              Price per night from

                              $218

                              Responds fast!
                              avg. 2 hours 48 minutes

                              Price per night from

                              $218

                              Distance approx 14.33 km from Centreville

                              (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

                                Distance approx 19.83 km from Centreville

                                (13) Excellent 

                                  24

                                  Premier Cottage in St. Michaels- In Town Location!

                                  Talbot County / St. Michaels

                                  St. Michaels house

                                  2 5 min stay varies

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

                                  Price per night from

                                  $207

                                  Responds fast!
                                  avg. 2 hours 48 minutes

                                  Price per night from

                                  $207

                                  Distance approx 6.05 km from Centreville Show on Map

                                  (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 11.01 km from Centreville

                                    (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 15.19 km from Centreville

                                      (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 12.86 km from Centreville

                                          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 13.08 km from Centreville

                                          (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

                                            Distance approx 19.43 km from Centreville

                                              58

                                              Great BD in Civil War House starting at 55$/night

                                              Maryland / Still Pond

                                              Still Pond house

                                              2 6 1 night min

                                              • 2 bedrooms
                                              • sleeps 6
                                              • 1 night min
                                              • Nearest beach 5 mi
                                              • Child Friendly
                                              • Air conditioning

                                              Price per night from

                                              $63

                                              Responds fast!
                                              avg. 2 hours 10 minutes

                                              Price per night from

                                              $63

                                              Distance approx 19.84 km from Centreville

                                              (3) Very Good 

                                                25

                                                Waterview Cottage In St. Michaels!

                                                Talbot County / St. Michaels

                                                St. Michaels cottage

                                                2 5 min stay varies

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

                                                Price per night from

                                                $218

                                                Responds fast!
                                                avg. 2 hours 48 minutes

                                                Price per night from

                                                $218

                                                Distance approx 19.68 km from Centreville

                                                  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 15.41 km from Centreville

                                                  (1) Excellent 

                                                    22

                                                    Sunview Cottage on Chesapeake Bay

                                                    Maryland / Chestertown

                                                    Chestertown house

                                                    2 5 3 nights min

                                                    • 2 bedrooms
                                                    • sleeps 5
                                                    • 3 nights min
                                                    • Beach / lakeside relaxation
                                                    • Child Friendly
                                                    • Air conditioning

                                                    Price per night from

                                                    $166

                                                    Responds fast!
                                                    avg. 3 hours 2 minutes

                                                    Price per night from

                                                    $166

                                                    Distance approx 19.85 km from Centreville

                                                      25

                                                      Annapolis Townhome w/Deck by Nature Trails & River

                                                      Maryland / Annapolis

                                                      Annapolis house

                                                      1 4 min stay varies

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

                                                      Price per night from

                                                      $102

                                                      Responds fast!
                                                      avg. 29 minutes

                                                      Price per night from

                                                      $102

                                                      Distance approx 11.45 km from Centreville

                                                      (1) Excellent 

                                                        7

                                                        Cozy Apartment in Chestertown

                                                        Maryland / Chestertown

                                                        Chestertown apartment

                                                        1 2 1 night min

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

                                                        Price per night from

                                                        $101

                                                        Responds fast!
                                                        avg. 3 hours 2 minutes

                                                        Price per night from

                                                        $101

                                                        Distance approx 13.59 km from Centreville

                                                          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 11.45 km from Centreville

                                                          (7) Excellent 

                                                            10

                                                            Charming Apartment in Historic Chestertown, MD

                                                            Maryland / Chestertown

                                                            Chestertown apartment

                                                            1 2 3 nights min

                                                            • 1 bedroom
                                                            • sleeps 2
                                                            • 3 nights min
                                                            • Nearest beach 24 mi
                                                            • Child Friendly
                                                            • Air conditioning

                                                            Price per night from

                                                            $114

                                                            Responds fast!
                                                            avg. 3 hours 2 minutes

                                                            Price per night from

                                                            $114

                                                            Distance approx 19 km from Centreville

                                                            (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 11.29 km from Centreville

                                                                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 10 minutes

                                                                Price per night from

                                                                $115

                                                                Distance approx 11.29 km from Centreville

                                                                  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 11.42 km from Centreville

                                                                    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 11.29 km from Centreville

                                                                      45

                                                                      Full-sized bedroom 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
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $46

                                                                      Responds fast!
                                                                      avg. 2 hours 10 minutes

                                                                      Price per night from

                                                                      $46

                                                                      Distance approx 15.19 km from Centreville

                                                                      (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 11.08 km from Centreville

                                                                        (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 17.94 km from Centreville

                                                                          (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 18.32 km from Centreville

                                                                              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