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78 Houses

    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

    $211

    Responds fast!
    avg. 36 minutes

    Price per night from

    $211

    Great rentals within 20 miles that match your search

    Distance approx 12.31 km from Shady Side

    (3) Very Good 

      15

      Halos'Haven Vacation Rental

      St. Michaels / McDaniel

      McDaniel house

      5 10 2 nights min

      • 5 bedrooms
      • sleeps 10
      • 2 nights min
      • Swimming pool
      • Child Friendly
      • Air conditioning

      Price per night from

      $821

      Price per night from

      $821

      Distance approx 5.75 km from Shady Side Show on Map

        26

        Annapolis Crows Nest Cottage: Chesapeake Bay View

        Maryland / Annapolis

        Annapolis villa

        5 20 min stay varies

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

        Price per night from

        $796

        Price per night from

        $796

        Distance approx 8.74 km from Shady Side Show on Map

          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

          $485

          Responds fast!
          avg. 36 minutes

          Price per night from

          $485

          Distance approx 16.76 km from Shady Side

            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

            $1,596

            Price per night from

            $1,596

            Distance approx 17.54 km from Shady Side

              9

              Holistic Getaway

              Maryland / Bowie

              Bowie house

              2 6 2 nights min

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

              Price per night from

              $166

              Price per night from

              $166

              Distance approx 8.21 km from Shady Side Show on Map

                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

                $586

                Price per night from

                $586

                Distance approx 18.85 km from Shady Side

                  18

                  Historic Waterfront Property with Wi-Fi and Dock

                  Talbot County / St. Michaels

                  St. Michaels house

                  3 8 2 nights min

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

                  Price per night from

                  $879

                  Responds fast!
                  avg. 3 hours 23 minutes

                  Price per night from

                  $879

                  Distance approx 9.29 km from Shady Side

                    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

                    $343

                    Price per night from

                    $343

                    Distance approx 13.65 km from Shady Side

                    (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. 2 hours 4 minutes

                      Price per night from

                      $327

                      Distance approx 14.3 km from Shady Side

                      (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

                        $441

                        Price per night from

                        $441

                        Distance approx 11.91 km from Shady Side

                        (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 13.76 km from Shady Side

                          (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 17.38 km from Shady Side

                            (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

                              $286

                              Price per night from

                              $286

                              Distance approx 9.27 km from Shady Side

                              (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

                                $326

                                Responds fast!
                                avg. 1 hour 1 minutes

                                Price per night from

                                $326

                                Distance approx 14.54 km from Shady Side

                                  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

                                  $281

                                  Price per night from

                                  $281

                                  Distance approx 14.13 km from Shady Side

                                  (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

                                    $440

                                    Price per night from

                                    $440

                                    Distance approx 8.68 km from Shady Side

                                    (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 16.02 km from Shady Side

                                      (3) Excellent 

                                        6

                                        Wellspring Manor & Spa

                                        Maryland / Largo

                                        Largo house

                                        5 10 1 night min

                                        • 5 bedrooms
                                        • sleeps 10
                                        • 1 night min

                                        Price per night from

                                        $1,917

                                        Price per night from

                                        $1,917

                                        Distance approx 9.82 km from Shady Side

                                          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 9.28 km from Shady Side

                                          (6) Excellent 

                                            19

                                            Charming and Spacious Annapolis Victorian

                                            Maryland / Annapolis

                                            Annapolis house

                                            6 12 min stay varies

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

                                            Price per night from

                                            $859

                                            Responds fast!
                                            avg. 1 hour 27 minutes

                                            Price per night from

                                            $859

                                            Distance approx 10.81 km from Shady Side

                                              29

                                              Custom Annapolis Home w/ Private Pool & Hot Tub!

                                              Maryland / Riva

                                              Riva house

                                              3 8 min stay varies

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

                                              Price per night from

                                              $330

                                              Responds fast!
                                              avg. 36 minutes

                                              Price per night from

                                              $330

                                              Distance approx 14.12 km from Shady Side

                                                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 8.99 km from Shady Side

                                                  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 8.79 km from Shady Side

                                                    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

                                                    $293

                                                    Price per night from

                                                    $293

                                                    Distance approx 16.51 km from Shady Side

                                                      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 15.91 km from Shady Side

                                                        6

                                                        Just Like Home (Private Bathrooms & Bedrooms)

                                                        Maryland / Gambrills

                                                        Gambrills townhouse

                                                        3 3 1 night min

                                                        • 3 bedrooms
                                                        • sleeps 3
                                                        • 1 night min
                                                        • Child Friendly

                                                        Price per night from

                                                        $18

                                                        Price per night from

                                                        $18

                                                        Distance approx 8.98 km from Shady Side

                                                        (3) Very Good 

                                                          30

                                                          Beautiful Murray Hill Home (Annapolis)

                                                          Maryland / Annapolis

                                                          Annapolis house

                                                          4 9 min stay varies

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

                                                          Price per night from

                                                          $485

                                                          Price per night from

                                                          $485

                                                          Distance approx 6.35 km from Shady Side Show on Map

                                                            4

                                                            Lochhaven house for rent

                                                            Maryland / Edgewater

                                                            Edgewater house

                                                            3 2 7 nights min

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

                                                            Price per night from

                                                            $114

                                                            Price per night from

                                                            $114

                                                            Distance approx 7.87 km from Shady Side

                                                            (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

                                                              $1,133

                                                              Price per night from

                                                              $1,133

                                                              Distance approx 9.69 km from Shady Side

                                                              (1) Excellent 

                                                                18

                                                                Stunning Home in the Heart of Downtown Annapolis

                                                                Maryland / Annapolis

                                                                Annapolis house

                                                                3 11 2 nights min

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

                                                                Price per night from

                                                                $796

                                                                Price per night from

                                                                $796

                                                                Distance approx 18.11 km from Shady Side

                                                                  6

                                                                  One Beautiful home come relax

                                                                  Maryland / Cheltenham

                                                                  Cheltenham house

                                                                  6 6 2 nights min

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

                                                                  Price per night from

                                                                  $206

                                                                  Price per night from

                                                                  $206

                                                                  Distance approx 6.32 km from Shady Side Show on Map

                                                                  (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

                                                                    $401

                                                                    Responds fast!
                                                                    avg. 36 minutes

                                                                    Price per night from

                                                                    $401

                                                                    Distance approx 9.5 km from Shady Side

                                                                    (1)  

                                                                      7

                                                                      Charming Townhouse - Steps to City Dock and USNA

                                                                      Maryland / Annapolis

                                                                      Annapolis house

                                                                      3 8 3 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 8
                                                                      • 3 nights min
                                                                      • Child Friendly
                                                                      • Car not necessary
                                                                      • Ask about pets

                                                                      Price per night from

                                                                      $514

                                                                      Price per night from

                                                                      $514

                                                                      Distance approx 12.75 km from Shady Side

                                                                      (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

                                                                        $1,758

                                                                        Price per night from

                                                                        $1,758

                                                                        Distance approx 10 km from Shady Side

                                                                        (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

                                                                          $457

                                                                          Responds fast!
                                                                          avg. 1 hour 7 minutes

                                                                          Price per night from

                                                                          $457

                                                                          Distance approx 9.61 km from Shady Side

                                                                            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

                                                                            $474

                                                                            Responds fast!
                                                                            avg. 1 hour 7 minutes

                                                                            Price per night from

                                                                            $474

                                                                            Distance approx 9.58 km from Shady Side

                                                                            (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 13 minutes

                                                                              Price per night from

                                                                              $365