Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Boats
Bungalows
Condos
Cottages
Estates
Farmhouses
Homes
Studios
Villas
Barns
Cabins
Castles
Chalets
Hotels
Lodges
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 with Online Booking(42)

42 Results
Book it Now!
3 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 9
    (26)
    Book it Now!
    3 - 7 night minimum stay
    • 6 BR,
    • 5 BA,
    • 1 HF BA,
    • Sleeps 16
      (16)
      Book it Now!
      3 night minimum stay
      • 4 BR,
      • 2 BA,
      • Sleeps 16
        (9)
        Book it Now!
        3 night minimum stay
        • 4 BR,
        • 3 BA,
        • 1 HF BA,
        • Sleeps 11
          (7)
          Book it Now!
          3 night minimum stay
          • 5 BR,
          • 3 BA,
          • Sleeps 12
            2 Reviews
            Book it Now!
            2 night minimum stay
            • 3 BR,
            • 2 BA,
            • Sleeps 8
              (26)
              Book it Now!
              2 - 7 night minimum stay
              • 4 BR,
              • 3 BA,
              • Sleeps 10
                (17)
                Book it Now!
                2 - 7 night minimum stay
                • 4 BR,
                • 3 BA,
                • Sleeps 12
                  (36)
                  Book it Now!
                  2 night minimum stay
                  • 3 BR,
                  • 2 BA,
                  • 1 HF BA,
                  • Sleeps 9
                    (12)
                    $200 - $350
                    per night
                    Book it Now!
                    2 night minimum stay
                    • 2 BR,
                    • 1 BA,
                    • 1 HF BA,
                    • Sleeps 8
                      (8)
                      Book it Now!
                      7 night minimum stay
                      • 4 BR,
                      • 2 BA,
                      • Sleeps 12
                        (4)
                        Book it Now!
                        3 - 7 night minimum stay
                        • 3 BR,
                        • 1 BA,
                        • Sleeps 6
                          (7)
                          Book it Now!
                          2 night minimum stay
                          • 3 BR,
                          • 2 BA,
                          • Sleeps 7
                            (8)
                            Book it Now!
                            2 - 7 night minimum stay
                            • 3 BR,
                            • 2 BA,
                            • Sleeps 6
                              (8)
                              Book it Now!
                              2 - 7 night minimum stay
                              • 4 BR,
                              • 2 BA,
                              • Sleeps 10
                                (4)
                                Book it Now!
                                2 night minimum stay
                                • 3 BR,
                                • 2 BA,
                                • Sleeps 10
                                  (3)
                                  Book it Now!
                                  3 night minimum stay
                                  • 4 BR,
                                  • 3 BA,
                                  • 1 HF BA,
                                  • Sleeps 8
                                    2 Reviews
                                    Book it Now!
                                    90 night minimum stay
                                    • 4 BR,
                                    • 4 BA,
                                    • 1 HF BA,
                                    • Sleeps 8
                                      Book it Now!
                                      • 3 BR,
                                      • 2 BA,
                                      • Sleeps 8
                                        Book it Now!
                                        2 night minimum stay
                                        • 3 BR,
                                        • 2 BA,
                                        • 1 HF BA,
                                        • Sleeps 6
                                          Book it Now!
                                          2 night minimum stay
                                          • 3 BR,
                                          • 2 BA,
                                          • 1 HF BA,
                                          • Sleeps 9
                                            2 Reviews
                                            Book it Now!
                                            2 night minimum stay
                                            • 3 BR,
                                            • 2 BA,
                                            • Sleeps 6
                                              20 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
                                                    (13)
                                                    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!
                                                        1 - 7 night minimum stay
                                                        • 2 BR,
                                                        • 1 BA,
                                                        • Sleeps 4
                                                          (8)
                                                          Book it Now!
                                                          • 5 BR,
                                                          • 3 BA,
                                                          • Sleeps 12
                                                            (8)
                                                            Book it Now!
                                                            2 - 5 night minimum stay
                                                            • 3 BR,
                                                            • 2 BA,
                                                            • Sleeps 8
                                                              (6)
                                                               

                                                              Recent Chesapeake Bay Reviews

                                                              Waterfront Retreat

                                                              5 of 5
                                                              If you enjoy water related activities in a tranquil setting then this is a must rental. We towed our boat from Ohio and launched it across the creek from the property. The dock easily accommodates boats of varying sizes. We were able to enjoy cruising around the picturesque creek which has easy access to the Bay. The crabbing was excellent and we had steamed crabs every night during our stay. Phil and Stephanie were very accommodating and the house was clean and well maintained. Every summer we rent waterfront homes in Maryland and I can honestly state that this was one of our best rentals.
                                                              • Submitted: Sep 9, 2014
                                                              • Stayed: Aug 2014

                                                              Perfect Weekend getaway!

                                                              5 of 5
                                                              Our family had a wonderful Labor day weekend at "Sandy Pines". The home was clean and well maintained. The owners and caretakers were very easy to work with. We fished, crabbed, kayaked, biked and swam the entire weekend that we did not even go to St. Michaels until the day we were leaving. When we return to the Chesapeake , we will be renting Sandy Pines again.
                                                              • Submitted: Sep 8, 2014
                                                              • Stayed: Sep 2014

                                                              Shhhhh! This place is a blissfully secluded gem.

                                                              5 of 5
                                                              The owner was very responsive and helpful. The place was well maintained and clean. It was nice having the beds made on arrival. The lawn was great for games. The beach was pleasant and we all enjoyed looking for the plentiful sea glass!
                                                              • Submitted: Aug 28, 2014
                                                              • Stayed: Aug 2014