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Gloucester: Houses, Cottages & More(17)

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Windward Cottage-Waterfront, Private Dock, Spectacular Views
    2 Bedrooms,
  • 1 Bathroom
    • , Sleeps 4
$110
per night

Windward Cottage-Waterfront, Private Dock, Spectacular Views

2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
  1. Chesapeake Bay - Northern Neck >
  2. Gloucester Cottage
#431956vb
    (3)
    Gorgeously Appointed Historic Waterfront Family Home
      5 Bedrooms,
    • 4 Bathrooms, 
    • 1 Half Bath
      • , Sleeps 9
    $550
    per night

    Gorgeously Appointed Historic Waterfront Family Home

    3 night minimum stay
    • 5 BR,
    • 4 BA,
    • 1 HF BA,
    • Sleeps 9
    1. Chesapeake Bay - Northern Neck >
    2. Gloucester House
    #284800
      Charming private cottage on 100 waterfront acres
        3 Bedrooms,
      • 2 Bathrooms
        • , Sleeps 5

      Charming private cottage on 100 waterfront acres

      • 3 BR,
      • 2 BA,
      • Sleeps 5
      1. Chesapeake Bay - Northern Neck >
      2. Gloucester Cottage
      #163681
        2 Reviews
        Idyllic Riverfront Estate Near Extraordinary Historic Sites
          4 Bedrooms,
        • 2 Bathrooms, 
        • 1 Half Bath
          • , Sleeps 8
        $500 - $550
        per night

        Idyllic Riverfront Estate Near Extraordinary Historic Sites

        5 night minimum stay
        • 4 BR,
        • 2 BA,
        • 1 HF BA,
        • Sleeps 8
        1. Chesapeake Bay - Northern Neck >
        2. Gloucester Estate
        #937035
          (4)
          Wonderful Retreat - Wareloch a Waterfront Estate in Tidewater
            4 Bedrooms,
          • 2 Bathrooms, 
          • 1 Half Bath
            • , Sleeps 10

          Wonderful Retreat - Wareloch a Waterfront Estate in Tidewater

          • 4 BR,
          • 2 BA,
          • 1 HF BA,
          • Sleeps 10
          1. Chesapeake Bay - Northern Neck >
          2. Gloucester Estate
          #287482
            (24)
            Cozy Cabin Getaway with Beautiful Sunsets on York River, minutes from Yorktown
              1 Bedrooms,
            • 1 Bathroom
              • , Sleeps 4
            $100 - $130
            per night

            Cozy Cabin Getaway with Beautiful Sunsets on York River, minutes from Yorktown

            1 - 2 night minimum stay
            • 1 BR,
            • 1 BA,
            • Sleeps 4
            1. Chesapeake Bay - Northern Neck >
            2. Gloucester Cabin
            #283342
              (53)
              Beachfront home with spectacular river views and private beach and yard!
                3 Bedrooms,
              • 1 Bathroom, 
              • 1 Half Bath
                • , Sleeps 8
              $207 - $250
              per night

              Beachfront home with spectacular river views and private beach and yard!

              2 night minimum stay
              • 3 BR,
              • 1 BA,
              • 1 HF BA,
              • Sleeps 8
              1. Chesapeake Bay - Northern Neck >
              2. Gloucester House
              #327009
                (12)
                Get-a-Way River House
                  4 Bedrooms,
                • 3 Bathrooms
                  • , Sleeps 10

                Get-a-Way River House

                • 4 BR,
                • 3 BA,
                • Sleeps 10
                1. Chesapeake Bay - Northern Neck >
                2. Gloucester House
                #926592
                  (13)
                  Romantic Waterfront Cottage Directly on the Beautiful North River
                    1 Bedrooms,
                  • 1 Bathroom
                    • , Sleeps 4
                  $1,500
                  per week

                  Romantic Waterfront Cottage Directly on the Beautiful North River

                  7 night minimum stay
                  • 1 BR,
                  • 1 BA,
                  • Sleeps 4
                  1. Chesapeake Bay - Northern Neck >
                  2. Gloucester Cottage
                  #3021375
                    Waterfront beach house. Private sand beach and Chesapeake Bay views fr
                      4 Bedrooms,
                    • 3 Bathrooms
                      • , Sleeps 8
                    $275
                    per night

                    Waterfront beach house. Private sand beach and Chesapeake Bay views fr

                    3 - 7 night minimum stay
                    • 4 BR,
                    • 3 BA,
                    • Sleeps 8
                    1. Chesapeake Bay - Northern Neck >
                    2. Gloucester House
                    #3005940
                      (12)
                      Waterview & Water Access, Luxurious Retreat
                        4 Bedrooms,
                      • 2 Bathrooms
                        • , Sleeps 12
                      $225
                      per night

                      Waterview & Water Access, Luxurious Retreat

                      2 night minimum stay
                      • 4 BR,
                      • 2 BA,
                      • Sleeps 12
                      1. Chesapeake Bay - Northern Neck >
                      2. Gloucester Farmhouse
                      #394282vb
                        (30)
                        Waterview & Access, Luxurious, Retreat-Near Williamsburg
                          4 Bedrooms,
                        • 2 Bathrooms
                          • , Sleeps 12
                        $225
                        per night

                        Waterview & Access, Luxurious, Retreat-Near Williamsburg

                        2 night minimum stay
                        • 4 BR,
                        • 2 BA,
                        • Sleeps 12
                        1. Chesapeake Bay - Northern Neck >
                        2. Gloucester Farmhouse
                        #394400vb
                          (28)
                          Relax, Refresh, Renew...Waterfront Cottage...Near Williamsburg
                            2 Bedrooms,
                          • 2 Bathrooms
                            • , Sleeps 6
                          $200
                          per night

                          Relax, Refresh, Renew...Waterfront Cottage...Near Williamsburg

                          2 night minimum stay
                          • 2 BR,
                          • 2 BA,
                          • Sleeps 6
                          1. Chesapeake Bay - Northern Neck >
                          2. Gloucester Cottage
                          #334542vb
                            (54)
                            Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg
                              2 Bedrooms,
                            • 2 Bathrooms
                              • , Sleeps 6
                            $200
                            per night

                            Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg

                            2 night minimum stay
                            • 2 BR,
                            • 2 BA,
                            • Sleeps 6
                            1. Chesapeake Bay - Northern Neck >
                            2. Gloucester Cottage
                            #334520vb
                              (51)
                              Beautiful Colonial House Amidst Tranquil Gardens!
                                3 Bedrooms,
                              • 2 Bathrooms
                                • , Sleeps 6
                              $245
                              per night

                              Beautiful Colonial House Amidst Tranquil Gardens!

                              2 night minimum stay
                              • 3 BR,
                              • 2 BA,
                              • Sleeps 6
                              1. Chesapeake Bay - Northern Neck >
                              2. Gloucester Cottage
                              #143693vb
                                (10)
                                Pet Friendly in a Beautiful, Relaxing Setting. Come See
                                  2 Bedrooms, Sleeps 4

                                Pet Friendly in a Beautiful, Relaxing Setting. Come See

                                • 2 BR,
                                • Sleeps 4
                                1. Chesapeake Bay - Northern Neck >
                                2. Gloucester Chateau / Country House
                                #383535vb
                                  (3)
                                  Secluded Waterview House with Private Dock Near Chesapeake Bay
                                    3 Bedrooms, Sleeps 7

                                  Secluded Waterview House with Private Dock Near Chesapeake Bay

                                  • 3 BR,
                                  • Sleeps 7
                                  1. Chesapeake Bay - Northern Neck >
                                  2. Gloucester House
                                  #237972vb
                                    (4)
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