Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Chesapeake Bay Cottage Rentals(33)

33 Results
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
    (62)
    2 - 3 night minimum stay
    • 3 BR,
    • 1 BA,
    • 1 HF BA,
    • Sleeps 6
      (26)
      2 - 3 night minimum stay
      • 2 BR,
      • 1 BA,
      • Sleeps 4
        (75)
        2 - 3 night minimum stay
        • 3 BR,
        • 2 BA,
        • Sleeps 6
          (32)
          3 night minimum stay
          • 4 BR,
          • 3 BA,
          • Sleeps 8
            (26)
            2 - 3 night minimum stay
            • 3 BR,
            • 3 BA,
            • Sleeps 7
              (40)
              2 - 3 night minimum stay
              • 3 BR,
              • 1 BA,
              • 1 HF BA,
              • Sleeps 6
                (29)
                2 - 3 night minimum stay
                • 3 BR,
                • 2 BA,
                • Sleeps 6
                  (48)
                  2 - 3 night minimum stay
                  • 4 BR,
                  • 2 BA,
                  • 1 HF BA,
                  • Sleeps 8
                    (17)
                    3 night minimum stay
                    • 2 BR,
                    • 1 BA,
                    • Sleeps 5
                      (12)
                      2 - 3 night minimum stay
                      • 3 BR,
                      • 2 BA,
                      • Sleeps 6
                        (30)
                        2 - 3 night minimum stay
                        • 2 BR,
                        • 1 BA,
                        • 1 HF BA,
                        • Sleeps 4
                          (30)
                          2 - 3 night minimum stay
                          • 3 BR,
                          • 3 BA,
                          • Sleeps 6
                            (17)
                            2 - 3 night minimum stay
                            • 4 BR,
                            • 3 BA,
                            • Sleeps 8
                              (20)
                              2 - 3 night minimum stay
                              • 2 BR,
                              • 1 BA,
                              • 1 HF BA,
                              • Sleeps 4
                                (16)
                                2 - 3 night minimum stay
                                • 3 BR,
                                • 3 BA,
                                • Sleeps 8
                                  (5)
                                  2 night minimum stay
                                  • 1 BR,
                                  • 1 HF BA,
                                  • Sleeps 2
                                    2 Reviews
                                    2 - 3 night minimum stay
                                    • 3 BR,
                                    • 2 BA,
                                    • Sleeps 6
                                      1 Review
                                      2 - 3 night minimum stay
                                      • 4 BR,
                                      • 2 BA,
                                      • 1 HF BA,
                                      • Sleeps 9
                                        (4)
                                        2 - 3 night minimum stay
                                        • 2 BR,
                                        • 2 BA,
                                        • Sleeps 4
                                          (3)
                                          2 - 3 night minimum stay
                                          • 4 BR,
                                          • 3 BA,
                                          • Sleeps 8
                                            2 Reviews
                                            2 - 3 night minimum stay
                                            • 2 BR,
                                            • 1 BA,
                                            • Sleeps 4
                                              2 Reviews
                                              2 - 3 night minimum stay
                                              • 7 BR,
                                              • 4 BA,
                                              • 1 HF BA,
                                              • Sleeps 14
                                                2 Reviews
                                                2 - 3 night minimum stay
                                                • 3 BR,
                                                • 2 BA,
                                                • Sleeps 5
                                                  2 night minimum stay
                                                  • 2 BR,
                                                  • Sleeps 4
                                                    1 Review
                                                    2 - 7 night minimum stay
                                                    • 2 BR,
                                                    • 1 BA,
                                                    • Sleeps 6
                                                      7 more choices from the HomeAway Network
                                                      3 - 7 night minimum stay
                                                      • 6 BR,
                                                      • 4 BA,
                                                      • 2 HF BA,
                                                      • Sleeps 16
                                                        (14)
                                                        Book it Now!
                                                        2 - 3 night minimum stay
                                                        • 2 BR,
                                                        • 1 BA,
                                                        • Sleeps 5
                                                          2 night minimum stay
                                                          • 3 BR,
                                                          • 2 BA,
                                                          • Sleeps 6
                                                            (17)
                                                            3 - 7 night minimum stay
                                                            • 3 BR,
                                                            • 2 BA,
                                                            • 1 HF BA,
                                                            • Sleeps 8
                                                               

                                                              Recent Chesapeake Bay Reviews

                                                              Charm on the Choptank

                                                              4 of 5
                                                              Rating Details: I was more than satisfied with the condition of the vacation rental. I was very happy with the location. The vacation rental was spotless. The property manager was very helpful. Overall, I recommend this vacation rental. Reviewer Comments: ESVR contacts and information are first rate. The cottage was just the right size for the three of us, two humans and a canine. Hard to imagine a better and more tranquil setting. Everything was as promised, clean and orderly. We enjoyed dock sitting, sunrises, and the peace and quiet. If it hadn't been for those pesky little black ants it would have been just about perfect. We'll definitely consider it next trip. Our first trip to Md. Eastern Shore was a very good one.
                                                              • Submitted: Sep 3, 2014
                                                              • Stayed: Jul 2014

                                                              Quick response.

                                                              5 of 5
                                                              This property is a great home away from home, they have taken a high end aprouch to a wonderful private experience. I had a great experience with this property and property manager. This is a great getaway exspecialy when DC was such a let down, this was the highlight of our vacation. Enjoy!
                                                              • Submitted: Aug 7, 2014
                                                              • Stayed: Jul 2014

                                                              So hard to leave

                                                              5 of 5
                                                              One of the best vacations we have ever had. We loved the vintage cottage, equipped with everything you would need. My husband and I had our 6 year old grandson along and it was great to just walk out the door to fishing and crabbing. Nice beach down the road. If you are looking for a relaxing, no rush vacation, this is the place to be. I would highly recommend to anyone. Thank you Bob and Maureen - hope to see you again.
                                                              • Submitted: Aug 8, 2013
                                                              • Stayed: Jul 2013