Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Chesapeake Bay Pet Friendly Cottage Rentals(53)

53 Results
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
    (62)
    2 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 night minimum stay
        • 3 BR,
        • 2 BA,
        • Sleeps 6
          (32)
          2 night minimum stay
          • 4 BR,
          • 3 BA,
          • Sleeps 8
            (26)
            2 - 7 night minimum stay
            • 2 BR,
            • 2 BA,
            • Sleeps 4
              (33)
              2 - 7 night minimum stay
              • 3 BR,
              • 2 BA,
              • Sleeps 9
                (5)
                2 night minimum stay
                • 3 BR,
                • 3 BA,
                • Sleeps 7
                  (41)
                  2 night minimum stay
                  • 3 BR,
                  • 1 BA,
                  • 1 HF BA,
                  • Sleeps 6
                    (29)
                    2 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)
                        Book it Now!
                        1 - 3 night minimum stay
                        • 2 BR,
                        • 1 BA,
                        • Sleeps 6
                          2 Reviews
                          2 night minimum stay
                          • 3 BR,
                          • 2 BA,
                          • 1 HF BA,
                          • Sleeps 7
                            (8)
                            3 night minimum stay
                            • 2 BR,
                            • 1 BA,
                            • Sleeps 5
                              (12)
                              Book it Now!
                              1 - 4 night minimum stay
                              • 1 BR,
                              • 1 BA,
                              • Sleeps 3
                                (17)
                                2 - 3 night minimum stay
                                • 3 BR,
                                • 2 BA,
                                • Sleeps 6
                                  (31)
                                  2 night minimum stay
                                  • 2 BR,
                                  • 1 BA,
                                  • 1 HF BA,
                                  • Sleeps 4
                                    (30)
                                    2 night minimum stay
                                    • 3 BR,
                                    • 3 BA,
                                    • Sleeps 6
                                      (17)
                                      2 - 3 night minimum stay
                                      • 2 BR,
                                      • 1 BA,
                                      • 1 HF BA,
                                      • Sleeps 4
                                        (17)
                                        3 - 7 night minimum stay
                                        • 3 BR,
                                        • 2 BA,
                                        • Sleeps 6
                                          (9)
                                          3 night minimum stay
                                          • 2 BR,
                                          • 2 BA,
                                          • Sleeps 6
                                            (24)
                                            2 night minimum stay
                                            • 3 BR,
                                            • 2 BA,
                                            • Sleeps 6
                                              1 Review
                                              2 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 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 night minimum stay
                                                      • 7 BR,
                                                      • 4 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 14
                                                        2 Reviews
                                                        2 night minimum stay
                                                        • 3 BR,
                                                        • 2 BA,
                                                        • Sleeps 5
                                                          Book it Now!
                                                          2 night minimum stay
                                                          • 2 BR,
                                                          • 2 BA,
                                                          • Sleeps 6
                                                            3 night minimum stay
                                                            • 2 BR,
                                                            • 1 BA,
                                                            • Sleeps 5
                                                              (7)
                                                               

                                                              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

                                                              Loverly!

                                                              5 of 5
                                                              A wonderful week in a wonderful cottage in a wonderful town. Steps to a small harbor and another block to the river view. Walked into town for great shops and restaurants (Don't miss Gregorio Gallery for great photos and gifts and Gina's at the top of the street for great shrimp tacos and crab dip!) Nice bike rides on the nature trail a few blocks from the cottage. Open the windows at night for the sound of silence interrupted only by the sounds of nature. The setting was ideal! Thanks!
                                                              • Submitted: Sep 1, 2014
                                                              • Stayed: Aug 2014

                                                              Awesome time

                                                              5 of 5
                                                              I spent 10 days in Deal Island's cottage and wished I could have stayed another 10. The cottage was clean and quaint and had everything I needed, I particularly enjoyed the screen porch where a breeze from the bay could be felt almost anytime. I was worried at first that the cottage would be too hot to sleep at night but the window ac was more than enough And I had to shut it off as it became too cold. Mo the owner and all the locals I met were welcoming and friendly and the island was quiet without all the beach traffic and tourist traps, just what I was looking for. My dogs had a great time walking and sleeping on the little beach where we spent much of our time since the weather was great, I read, ate and relaxed. Hopefully I can go back next year
                                                              • Submitted: Aug 16, 2014
                                                              • Stayed: Aug 2014