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79 Houses

    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

    $280

    Price per night from

    $280

    (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

      $440

      Price per night from

      $440

        6

        Cottage 1b at Grandview Pleasure Point

        Talbot County / Bozman

        Bozman cottage

        1 2 7 nights min

        • 1 bedroom
        • sleeps 2
        • 7 nights min
        • Swimming pool
        • Ask about children
        • Air conditioning

        Price per night from

        $280

        Price per night from

        $280

        (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.

          Price per night from

          $787

          Price per night from

          $787

          Great rentals within 20 miles that match your search

          Distance approx 16.63 km from Bozman

          (12) Very Good 

            31

            Stunning, Newer Chesapeake Waterfront Estate, Pool - 6/7 Bedrms 5 Baths

            Maryland / Cambridge

            Cambridge house

            6 20 min stay varies

            • 6 bedrooms
            • sleeps 20
            • min stay varies
            • Beach / lakeside relaxation
            • Nearest beach 0.1 mi
            • Swimming pool
            “Outstanding Vacation Rental” Our extended family (22 people - 13A/9K) had a great week at Saddle Beach. The house was beautiful and in very good condition. The option of being in the pool or the river during the day was wonderful. The house was cle

            Price per night from

            $569

            Price per night from

            $569

            Distance approx 14.43 km from Bozman

              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

              $792

              Price per night from

              $792

              Distance approx 14.81 km from Bozman

                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

                $570

                Price per night from

                $570

                Distance approx 18.08 km from Bozman

                  23

                  Charming Eastport Home

                  Maryland / Annapolis

                  Annapolis house

                  3 8 5 nights min

                  • 3 bedrooms
                  • sleeps 8
                  • 5 nights min
                  • Child Friendly
                  • Air conditioning
                  • Private garden

                  Price per night from

                  $342

                  Price per night from

                  $342

                  Distance approx 19.14 km from Bozman

                    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

                    $114

                    Price per night from

                    $114

                    Distance approx 17.18 km from Bozman

                      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

                      $1,595

                      Price per night from

                      $1,595

                      Distance approx 2.94 km from Bozman

                        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

                        $325

                        Price per night from

                        $325

                        Distance approx 5.35 km from Bozman

                        (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

                          $411

                          Price per night from

                          $411

                          Distance approx 16.4 km from Bozman

                            16

                            Choptank River View House

                            Maryland / Cambridge

                            Cambridge house

                            6 14 3 nights min

                            • 6 bedrooms
                            • sleeps 14
                            • 3 nights min
                            • Beach / lakeside relaxation
                            • Nearest beach 0 mi
                            • Air conditioning

                            Price per night from

                            $1,140

                            Price per night from

                            $1,140

                            Distance approx 11.29 km from Bozman

                            (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

                              $1,710

                              Responds fast!
                              avg. 11 minutes

                              Price per night from

                              $1,710

                              Distance approx 16.96 km from Bozman

                                42

                                Waterfront Room Rentals 2 with Private Beach

                                Talbot County / Trappe

                                Trappe room

                                1 2 min stay varies

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

                                Price per night from

                                $114

                                Responds fast!
                                avg. 1 hour 38 minutes

                                Price per night from

                                $114

                                Distance approx 18.61 km from Bozman

                                (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

                                  Price per night from

                                  $485

                                  Price per night from

                                  $485

                                  Distance approx 14.19 km from Bozman

                                  (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

                                    $438

                                    Price per night from

                                    $438

                                    Distance approx 2.73 km from Bozman

                                    (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

                                      $428

                                      Price per night from

                                      $428

                                      Distance approx 13.93 km from Bozman

                                      (10) Excellent 

                                        50

                                        Cottage at Heron Cove, Chesapeake Bay, Cambridge

                                        Maryland / Cambridge

                                        Cambridge cottage

                                        3 5 7 nights min

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

                                        Price per night from

                                        $168

                                        Price per night from

                                        $168

                                        Distance approx 11.29 km from Bozman

                                        (1) Excellent 

                                          32

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

                                          Kent Island / Chester

                                          Chester house

                                          4 10 2 nights min

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

                                          Price per night from

                                          $1,368

                                          Responds fast!
                                          avg. 11 minutes

                                          Price per night from

                                          $1,368

                                          Distance approx 12.71 km from Bozman

                                          (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,

                                            Price per night from

                                            $325

                                            Responds fast!
                                            avg. 2 hours 24 minutes

                                            Price per night from

                                            $325

                                            Distance approx 10.91 km from Bozman

                                            (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

                                              $456

                                              Responds fast!
                                              avg. 1 hour 7 minutes

                                              Price per night from

                                              $456

                                              Distance approx 14.61 km from Bozman

                                                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

                                                $342

                                                Price per night from

                                                $342

                                                Distance approx 19.45 km from Bozman

                                                (20) Excellent 

                                                  25

                                                  *BOOK NOW* Beautiful Cottage in historic Annapolis

                                                  Maryland / Annapolis

                                                  Annapolis cottage

                                                  3 6 2 nights min

                                                  • 3 bedrooms
                                                  • sleeps 6
                                                  • 2 nights min
                                                  • Beach / lakeside relaxation
                                                  • Nearest beach 1 mi
                                                  • Child Friendly

                                                  Price per night from

                                                  $365

                                                  Responds fast!
                                                  avg. 2 hours 19 minutes

                                                  Price per night from

                                                  $365

                                                  Distance approx 2.61 km from Bozman

                                                  (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

                                                    $598

                                                    Price per night from

                                                    $598

                                                    Distance approx 0.1 km from Bozman

                                                      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

                                                      $228

                                                      Price per night from

                                                      $228

                                                      Distance approx 18.53 km from Bozman

                                                      (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

                                                        $325

                                                        Responds fast!
                                                        avg. 1 hour 1 minutes

                                                        Price per night from

                                                        $325

                                                        Distance approx 12.85 km from Bozman

                                                          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

                                                          $223

                                                          Responds fast!
                                                          avg. 41 minutes

                                                          Price per night from

                                                          $223

                                                          Distance approx 4.91 km from Bozman

                                                            23

                                                            Waterfront 5 bd 2 ba colonial in Tilghman Island

                                                            Talbot County / Tilghman

                                                            Tilghman house

                                                            5 12 1 night min

                                                            • 5 bedrooms
                                                            • sleeps 12
                                                            • 1 night min
                                                            • Nearest beach 52 mi
                                                            • Child Friendly
                                                            • Air conditioning

                                                            Price per night from

                                                            $191

                                                            Responds fast!
                                                            avg. 2 hours 49 minutes

                                                            Price per night from

                                                            $191

                                                            Distance approx 18.04 km from Bozman

                                                            (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

                                                              $285

                                                              Responds fast!
                                                              avg. 27 minutes

                                                              Price per night from

                                                              $285

                                                              Distance approx 7.57 km from Bozman

                                                              (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

                                                                $456

                                                                Responds fast!
                                                                avg. 41 minutes

                                                                Price per night from

                                                                $456

                                                                Distance approx 11.2 km from Bozman

                                                                  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

                                                                  $473

                                                                  Responds fast!
                                                                  avg. 1 hour 7 minutes

                                                                  Price per night from

                                                                  $473

                                                                  Distance approx 16.96 km from Bozman

                                                                  (1) Very Good 

                                                                    34

                                                                    Waterfront Room Rentals 1 with Private Beach

                                                                    Talbot County / Trappe

                                                                    Trappe room

                                                                    1 2 min stay varies

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

                                                                    Price per night from

                                                                    $149

                                                                    Responds fast!
                                                                    avg. 1 hour 38 minutes

                                                                    Price per night from

                                                                    $149

                                                                    Distance approx 15.05 km from Bozman

                                                                    (2)  

                                                                      26

                                                                      3BR Annapolis Home on Oyster Creek w/Amazing Views

                                                                      Maryland / Annapolis

                                                                      Annapolis house

                                                                      3 9 2 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 9
                                                                      • 2 nights min
                                                                      • Child Friendly
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $914

                                                                      Responds fast!
                                                                      avg. 41 minutes

                                                                      Price per night from

                                                                      $914

                                                                      Distance approx 17.76 km from Bozman

                                                                        24

                                                                        Charming Artists Home in Eastport/Annapolis

                                                                        Maryland / Annapolis

                                                                        Annapolis house

                                                                        3 6 3 nights min

                                                                        • 3 bedrooms
                                                                        • sleeps 6
                                                                        • 3 nights min
                                                                        • Ask about children
                                                                        • Air conditioning

                                                                        Price per night from

                                                                        $428

                                                                        Price per night from

                                                                        $428

                                                                        Distance approx 9.61 km from Bozman

                                                                          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

                                                                          $486

                                                                          Responds fast!
                                                                          avg. 41 minutes

                                                                          Price per night from

                                                                          $486

                                                                          Distance approx 16.96 km from Bozman

                                                                            44

                                                                            Waterfront Room Rentals 3 with Private Beach

                                                                            Talbot County / Trappe

                                                                            Trappe room

                                                                            1 2 min stay varies

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

                                                                            Price per night from

                                                                            $115

                                                                            Responds fast!
                                                                            avg. 1 hour 38 minutes

                                                                            Price per night from

                                                                            $115

                                                                            Distance approx 19.69 km from Bozman

                                                                            (1) Excellent 

                                                                              18

                                                                              Luxury Boat & Bed 78' Motor Yacht "Laid Off"

                                                                              Maryland / Edgewater

                                                                              Edgewater yacht

                                                                              4 10 1 night min

                                                                              • 4 bedrooms
                                                                              • sleeps 10
                                                                              • 1 night min
                                                                              • Child Friendly
                                                                              • Air conditioning
                                                                              • Pet Friendly

                                                                              Price per night from

                                                                              $1,129

                                                                              Price per night from

                                                                              $1,129