Vacation Rentals & Cabins in Wittman

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80 Houses

(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

    $1,115

    Price per night from

    $1,115

    Great rentals within 20 miles that match your search

    Distance approx 12.73 km from Wittman

    (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 4.1 km from Wittman Show on Map

      (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

        $427

        Price per night from

        $427

        Distance approx 16.57 km from Wittman

        (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

          $484

          Price per night from

          $484

          Distance approx 15.72 km from Wittman

            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 10.96 km from Wittman

            (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

              $326

              Responds fast!
              avg. 2 hours 24 minutes

              Price per night from

              $326

              Distance approx 9.51 km from Wittman

              (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

                $1,369

                Responds fast!
                avg. 11 minutes

                Price per night from

                $1,369

                Distance approx 2.47 km from Wittman Show on Map

                (3) Excellent 

                  24

                  Best sunrise in St. Michaels....Broadview Bay House

                  Talbot County / St. Michaels

                  St. Michaels house

                  6 12 min stay varies

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

                  Price per night from

                  $598

                  Price per night from

                  $598

                  Distance approx 17.22 km from Wittman

                    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 11.21 km from Wittman

                      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. 40 minutes

                      Price per night from

                      $223

                      Distance approx 3.85 km from Wittman Show on Map

                      (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

                        $1,144

                        Responds fast!
                        avg. 3 hours 35 minutes

                        Price per night from

                        $1,144

                        Distance approx 5.53 km from Wittman Show on Map

                        (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. 40 minutes

                          Price per night from

                          $458

                          Distance approx 18.99 km from Wittman

                          (5) Average 

                            55

                            Waterfront Vacation Home with Private Beach

                            Talbot County / Trappe

                            Trappe house

                            3 6 2 nights min

                            • 3 bedrooms
                            • sleeps 6
                            • 2 nights min
                            • Beach / lakeside relaxation
                            • Nearest beach 97 mi
                            • Child Friendly

                            Price per night from

                            $378

                            Responds fast!
                            avg. 1 hour 38 minutes

                            Price per night from

                            $378

                            Distance approx 19.8 km from Wittman

                              7

                              2. Private 20 acre waterfront estate - studio apt

                              Maryland / Annapolis

                              Annapolis apartment

                              1 2 1 night min

                              • 1 bedroom
                              • sleeps 2
                              • 1 night min
                              • Ask about pets

                              Price per night from

                              $343

                              Price per night from

                              $343

                              Distance approx 6.96 km from Wittman Show on Map

                                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

                                $571

                                Price per night from

                                $571

                                Distance approx 14.07 km from Wittman

                                  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

                                  $572

                                  Price per night from

                                  $572

                                  Distance approx 16.87 km from Wittman

                                  (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

                                    $286

                                    Responds fast!
                                    avg. 1 hour 38 minutes

                                    Price per night from

                                    $286

                                    Distance approx 4.33 km from Wittman Show on Map

                                    (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

                                      $262

                                      Price per night from

                                      $262

                                      Distance approx 3.86 km from Wittman Show on Map

                                      (9) 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 2.89 km from Wittman 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

                                          $372

                                          Price per night from

                                          $372

                                          Distance approx 12.51 km from Wittman

                                            55

                                            Charming Annapolis home with stunning water views

                                            Maryland / Annapolis

                                            Annapolis house

                                            4 11 5 nights min

                                            • 4 bedrooms
                                            • sleeps 11
                                            • 5 nights min
                                            • Child Friendly
                                            • Pet Friendly

                                            Price per night from

                                            $572

                                            Price per night from

                                            $572

                                            Distance approx 3.87 km from Wittman Show on Map

                                            (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

                                              $206

                                              Responds fast!
                                              avg. 2 hours 48 minutes

                                              Price per night from

                                              $206

                                              Distance approx 18.99 km from Wittman

                                              (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 8.93 km from Wittman

                                                (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 1.99 km from Wittman Show on Map

                                                    12

                                                    Harris Cove Cottages LLC

                                                    Talbot County / St. Michaels

                                                    St. Michaels cottage

                                                    1 4 1 night min

                                                    • 1 bedroom
                                                    • sleeps 4
                                                    • 1 night min
                                                    • Child Friendly
                                                    • Air conditioning

                                                    Price per night from

                                                    $229

                                                    Price per night from

                                                    $229

                                                    Distance approx 9.39 km from Wittman

                                                      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 4.29 km from Wittman Show on Map

                                                      (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

                                                        $789

                                                        Price per night from

                                                        $789

                                                        Distance approx 4.29 km from Wittman Show on Map

                                                        (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 4.7 km from Wittman Show on Map

                                                          (1) Excellent 

                                                            18

                                                            St. Michaels Waterfront Home W/Dock for 2 boats

                                                            Talbot County / Neavitt

                                                            Neavitt house

                                                            2 5 min stay varies

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

                                                            Price per night from

                                                            $258

                                                            Responds fast!
                                                            avg. 2 hours 3 minutes

                                                            Price per night from

                                                            $258

                                                            Distance approx 16.65 km from Wittman

                                                            (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

                                                              $795

                                                              Price per night from

                                                              $795

                                                              Distance approx 4.12 km from Wittman Show on Map

                                                                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

                                                                $326

                                                                Price per night from

                                                                $326

                                                                Distance approx 17.17 km from Wittman

                                                                  4

                                                                  Perfect Annapolis with Lots of Parking & Hot Tub

                                                                  Maryland / Annapolis

                                                                  Annapolis townhouse

                                                                  4 10 2 nights min

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

                                                                  Price per night from

                                                                  $566

                                                                  Price per night from

                                                                  $566

                                                                  Distance approx 5.67 km from Wittman Show on Map

                                                                    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 16 km from Wittman

                                                                    (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

                                                                      $286

                                                                      Responds fast!
                                                                      avg. 27 minutes

                                                                      Price per night from

                                                                      $286

                                                                      Distance approx 12.04 km from Wittman

                                                                        17

                                                                        Serene Waterfront Apartment on Kent Island

                                                                        Kent Island / Stevensville

                                                                        Stevensville apartment

                                                                        1 2 min stay varies

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

                                                                        Price per night from

                                                                        $172

                                                                        Price per night from

                                                                        $172

                                                                        Distance approx 12.05 km from Wittman

                                                                          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 18.38 km from Wittman

                                                                          (2) Excellent 

                                                                            10

                                                                            C/ean & Cozy

                                                                            Maryland / Annapolis

                                                                            Annapolis room

                                                                            1 2 1 night min

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

                                                                            Price per night from

                                                                            $68

                                                                            Price per night from

                                                                            $68

                                                                            Distance approx 15.47 km from Wittman

                                                                              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

                                                                              $1,600

                                                                              Price per night from

                                                                              $1,600