Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Boats
Bungalows
Condos
Cottages
Estates
Farmhouses
Homes
Lodges
Studios
Villas
Barns
Cabins
Castles
Chalets
Hotels
Townhomes
Yachts

Location Type

Even More Filters

Features

Managed By

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

Chesapeake Bay Vacation Home Rentals(167)

167 Results
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
    (13)
    • 7 BR,
    • 6 BA,
    • Sleeps 20
      3 night minimum stay
      • 5 BR,
      • 3 BA,
      • 1 HF BA,
      • Sleeps 13
        1 Review
        2 night minimum stay
        • 4 BR,
        • 3 BA,
        • Sleeps 8
          2 - 7 night minimum stay
          • 4 BR,
          • 1 BA,
          • Sleeps 8
            (8)
            • 5 BR,
            • 4 BA,
            • 1 HF BA,
            • Sleeps 10
              • 4 BR,
              • 3 BA,
              • 1 HF BA,
              • Sleeps 17
                (12)
                • 6 BR,
                • 3 BA,
                • Sleeps 12
                  (3)
                  • 6 BR,
                  • Sleeps 13
                    (7)
                    68 more choices from the HomeAway Network
                    Book it Now!
                    2 - 7 night minimum stay
                    • 3 BR,
                    • 2 BA,
                    • Sleeps 7
                      (20)
                      Book it Now!
                      2 - 3 night minimum stay
                      • 3 BR,
                      • 1 BA,
                      • Sleeps 6
                        (11)
                        $350 - $590
                        per night
                        Book it Now!
                        2 - 7 night minimum stay
                        • 3 BR,
                        • 3 BA,
                        • 2 HF BA,
                        • Sleeps 10
                          (12)
                          Book it Now!
                          2 night minimum stay
                          • 2 BR,
                          • 2 BA,
                          • Sleeps 6
                            (9)
                            Book it Now!
                            3 - 7 night minimum stay
                            • 4 BR,
                            • 2 BA,
                            • 1 HF BA,
                            • Sleeps 12
                              (10)
                              Book it Now!
                              • 5 BR,
                              • 3 BA,
                              • Sleeps 12
                                (8)
                                Book it Now!
                                1 - 7 night minimum stay
                                • 2 BR,
                                • 1 BA,
                                • Sleeps 4
                                  (7)
                                  Book it Now!
                                  2 - 5 night minimum stay
                                  • 3 BR,
                                  • 2 BA,
                                  • Sleeps 8
                                    (6)
                                    $140 - $200
                                    per night
                                    2 night minimum stay
                                    • 3 BR,
                                    • 1 BA,
                                    • 1 HF BA,
                                    • Sleeps 7
                                      (15)
                                      3 night minimum stay
                                      • 3 BR,
                                      • 3 BA,
                                      • Sleeps 12
                                        (19)
                                        Book it Now!
                                        1 - 2 night minimum stay
                                        • 4 BR,
                                        • 2 BA,
                                        • Sleeps 9
                                          (8)
                                          2 night minimum stay
                                          • 3 BR,
                                          • 2 BA,
                                          • 1 HF BA,
                                          • Sleeps 6
                                            (16)
                                            $550 - $700
                                            per night
                                            Book it Now!
                                            2 - 7 night minimum stay
                                            • 4 BR,
                                            • 3 BA,
                                            • Sleeps 12
                                              (5)
                                              Book it Now!
                                              3 - 7 night minimum stay
                                              • 5 BR,
                                              • 3 BA,
                                              • 1 HF BA,
                                              • Sleeps 12
                                                (5)
                                                2 night minimum stay
                                                • 2 BR,
                                                • 1 BA,
                                                • 1 HF BA,
                                                • Sleeps 6
                                                  (12)
                                                  $250
                                                  per night
                                                  Book it Now!
                                                  3 night minimum stay
                                                  • 2 BR,
                                                  • 1 BA,
                                                  • 1 HF BA,
                                                  • Sleeps 4
                                                    (4)
                                                    Book it Now!
                                                    • 2 BR,
                                                    • 2 BA,
                                                    • Sleeps 8
                                                      (3)
                                                      Book it Now!
                                                      2 - 7 night minimum stay
                                                      • 4 BR,
                                                      • 4 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 11
                                                        (24)
                                                        2 - 7 night minimum stay
                                                        • 4 BR,
                                                        • 1 BA,
                                                        • 1 HF BA,
                                                        • Sleeps 10
                                                          (15)
                                                          Book it Now!
                                                          2 - 7 night minimum stay
                                                          • 3 BR,
                                                          • 2 BA,
                                                          • Sleeps 9
                                                            (18)
                                                            Book it Now!
                                                            2 - 7 night minimum stay
                                                            • 5 BR,
                                                            • 4 BA,
                                                            • Sleeps 14
                                                              2 Reviews
                                                               

                                                              Recent Chesapeake Bay Reviews

                                                              Enjoyed our stay immensely

                                                              5 of 5
                                                              WOW!!!! What a wonderful vacation house,spacious rooms open up to a gorgeous view of the bay...kitchen has everything you need,big,clean bathrooms,powder room- great array of movies,books, games,bicycles,wagon for the beach! The owner entirely opens up this home for guests,nothing is off limits...the beds are super comfy,just a great place to vacation,Thank you!
                                                              • Submitted: Aug 19, 2014
                                                              • Stayed: Aug 2014

                                                              Wonderful Weekend

                                                              5 of 5
                                                              We stayed at this house the weekend of the Eagleman Triathlon and it was a wonderful getaway, The house is beautiful, the location was idyllic, we especially enjoyed the sunsets, bullfrogs, and deer. This house was truly a relaxing retreat.
                                                              • Submitted: Jun 25, 2012
                                                              • Stayed: Jun 2012

                                                              Great location for family reunion!

                                                              5 of 5
                                                              Very family friendly. Comfortable furnishings with lots of room for kids and grownups to spread out. Beautiful beach for fossil hunting, fishing, swimming, relaxing. Owner is kind, friendly and responds quickly to questions, problems, etc. Would come back every year!!!
                                                              • Submitted: Aug 23, 2010
                                                              • Stayed: Jun 2010