Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartment
Bungalow
Condo
Cottage
Estate
Homes
Homes
Lodge
Studio
Villa
Barn
Boat
Cabin
Castle
Chalet
Hotel
Townhome
Yacht

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Chesapeake Bay Waterfront Vacation Home Rentals(121)

121 Results
3 - 7 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 10
    (23)
    Book it Now!
    3 - 7 night minimum stay
    • 6 BR,
    • 5 BA,
    • 1 HF BA,
    • Sleeps 18
      (16)
      2 - 3 night minimum stay
      • 4 BR,
      • 2 BA,
      • Sleeps 8
        (39)
        2 - 3 night minimum stay
        • 4 BR,
        • 2 BA,
        • 1 HF BA,
        • Sleeps 8
          (30)
          2 - 3 night minimum stay
          • 7 BR,
          • 5 BA,
          • 1 HF BA,
          • Sleeps 22
            (41)
            2 - 7 night minimum stay
            • 4 BR,
            • 3 BA,
            • 1 HF BA,
            • Sleeps 10
              (14)
              2 - 3 night minimum stay
              • 7 BR,
              • 7 BA,
              • 1 HF BA,
              • Sleeps 22
                (15)
                Book it Now!
                3 - 7 night minimum stay
                • 4 BR,
                • 2 BA,
                • Sleeps 9
                  (22)
                  $350 - $450
                  per night
                  Book it Now!
                  2 - 5 night minimum stay
                  • 3 BR,
                  • 2 BA,
                  • Sleeps 8
                    (14)
                    3 - 7 night minimum stay
                    • 4 BR,
                    • 4 BA,
                    • Sleeps 8
                      (30)
                      3 - 7 night minimum stay
                      • 5 BR,
                      • 3 BA,
                      • 1 HF BA,
                      • Sleeps 18
                        (9)
                        3 - 7 night minimum stay
                        • 4 BR,
                        • 3 BA,
                        • 1 HF BA,
                        • Sleeps 8
                          2 Reviews
                          3 night minimum stay
                          • 3 BR,
                          • 2 BA,
                          • Sleeps 6
                            2 Reviews
                            2 night minimum stay
                            • 4 BR,
                            • 4 BA,
                            • Sleeps 8
                              (15)
                              Book it Now!
                              3 night minimum stay
                              • 4 BR,
                              • 3 BA,
                              • 1 HF BA,
                              • Sleeps 11
                                (5)
                                2 - 7 night minimum stay
                                • 3 BR,
                                • 2 BA,
                                • Sleeps 8
                                  (11)
                                  Book it Now!
                                  3 night minimum stay
                                  • 5 BR,
                                  • 3 BA,
                                  • Sleeps 12
                                    3 - 7 night minimum stay
                                    • 7 BR,
                                    • 3 BA,
                                    • 1 HF BA,
                                    • Sleeps 18
                                      (5)
                                      2 - 7 night minimum stay
                                      • 4 BR,
                                      • 3 BA,
                                      • Sleeps 8
                                        1 Review
                                        3 - 7 night minimum stay
                                        • 6 BR,
                                        • 3 BA,
                                        • Sleeps 12
                                          (3)
                                          2 - 7 night minimum stay
                                          • 3 BR,
                                          • 2 BA,
                                          • Sleeps 9
                                            1 Review
                                            3 - 7 night minimum stay
                                            • 6 BR,
                                            • 5 BA,
                                            • 1 HF BA,
                                            • Sleeps 15
                                              (7)
                                              3 - 4 night minimum stay
                                              • 4 BR,
                                              • 2 BA,
                                              • 1 HF BA,
                                              • Sleeps 9
                                                (9)
                                                2 - 7 night minimum stay
                                                • 5 BR,
                                                • 4 BA,
                                                • Sleeps 10
                                                  (12)
                                                  7 night minimum stay
                                                  • 4 BR,
                                                  • 3 BA,
                                                  • Sleeps 12
                                                    (12)
                                                    • 4 BR,
                                                    • 2 BA,
                                                    • Sleeps 10
                                                      (7)
                                                      2 - 3 night minimum stay
                                                      • 3 BR,
                                                      • 3 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 8
                                                        (12)
                                                        3 night minimum stay
                                                        • 2 BR,
                                                        • 2 BA,
                                                        • 1 HF BA,
                                                        • Sleeps 6
                                                          (4)
                                                          2 - 7 night minimum stay
                                                          • 8 BR,
                                                          • 6 BA,
                                                          • Sleeps 22
                                                            (18)
                                                             

                                                            Recent Chesapeake Bay Reviews

                                                            serene, idyllic, very special

                                                            5 of 5
                                                            We are a family of 16 with an age span between 70 and two years. The house easily accommodated all of us - the bedrooms are comfortable, private and the nights quiet. The house is fully equipped for any need be it steaming crabs, toasting marshmallows and the ordinary daily meal. The children swam in the river, their favorite occupation, or in the pool, and hiked through the extensive forest and fields and visited the historic windmill with George Radcliffe as historical guide. An abundance of wildlife provided other pleasures. The property is beautiful and each hour of the day revealed a unique ambience. The hosts, George and Jackie Radcliffe are warm, generous and gracious. The Radcliffe family has a vast amount of history of its own which adds to the atmosphere of the house. We couldn't have asked for a more idyllic setting for our family reunion.
                                                            • Submitted: Aug 7, 2014
                                                            • Stayed: Jul 2014

                                                            Great family vacation spot!!!

                                                            5 of 5
                                                            Great location on the water with lots of room for our large multi-generational family. Quiet and secluded with plenty of waterfront and water toys!! Looking forward to next year to do it again!! Manager was very helpful and accommodating to our needs.
                                                            • Submitted: Aug 6, 2014
                                                            • Stayed: Jul 2014

                                                            tranquility at its finest

                                                            5 of 5
                                                            no complaints! walking distance to everything clean and very friendly community community private beach and peer clean short drive to clean dog friendly beach peaceful, relaxing home atmosphere would absolutely stay there again
                                                            • Submitted: Jul 30, 2014
                                                            • Stayed: Jul 2014