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 Vacation Rentals with Internet Access(263)

263 Results
Book it Now!
3 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 9
    (25)
    3 night minimum stay
    • 5 BR,
    • 4 BA,
    • Sleeps 10
      (24)
      2 - 3 night minimum stay
      • 2 BR,
      • 1 BA,
      • 1 HF BA,
      • Sleeps 4
        (62)
        Book it Now!
        3 - 7 night minimum stay
        • 6 BR,
        • 5 BA,
        • 1 HF BA,
        • Sleeps 16
          (16)
          2 - 3 night minimum stay
          • 4 BR,
          • 2 BA,
          • Sleeps 8
            (42)
            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
                (74)
                2 - 3 night minimum stay
                • 4 BR,
                • 2 BA,
                • 1 HF BA,
                • Sleeps 8
                  (32)
                  2 - 3 night minimum stay
                  • 7 BR,
                  • 5 BA,
                  • 1 HF BA,
                  • Sleeps 22
                    (42)
                    2 - 3 night minimum stay
                    • 5 BR,
                    • 4 BA,
                    • 1 HF BA,
                    • Sleeps 13
                      (24)
                      2 - 3 night minimum stay
                      • 7 BR,
                      • 7 BA,
                      • 1 HF BA,
                      • Sleeps 22
                        (16)
                        2 - 3 night minimum stay
                        • 3 BR,
                        • 2 BA,
                        • Sleeps 8
                          (33)
                          2 - 3 night minimum stay
                          • 3 BR,
                          • 2 BA,
                          • Sleeps 6
                            (31)
                            3 night minimum stay
                            • 4 BR,
                            • 3 BA,
                            • Sleeps 8
                              (25)
                              4 night minimum stay
                              • 5 BR,
                              • 5 BA,
                              • Sleeps 12
                                (13)
                                Book it Now!
                                2 night minimum stay
                                • 3 BR,
                                • 2 BA,
                                • Sleeps 6
                                  (7)
                                  2 - 3 night minimum stay
                                  • 4 BR,
                                  • 4 BA,
                                  • Sleeps 10
                                    (9)
                                    Book it Now!
                                    3 night minimum stay
                                    • 4 BR,
                                    • 2 BA,
                                    • Sleeps 16
                                      (9)
                                      3 - 7 night minimum stay
                                      • 4 BR,
                                      • 4 BA,
                                      • Sleeps 8
                                        (32)
                                        2 - 3 night minimum stay
                                        • 7 BR,
                                        • 4 BA,
                                        • 2 HF BA,
                                        • Sleeps 20
                                          (8)
                                          3 night minimum stay
                                          • 3 BR,
                                          • 2 BA,
                                          • Sleeps 6
                                            (65)
                                            Book it Now!
                                            2 night minimum stay
                                            • 2 BR,
                                            • 2 BA,
                                            • Sleeps 6
                                              (3)
                                              3 - 4 night minimum stay
                                              • 6 BR,
                                              • 5 BA,
                                              • 1 HF BA,
                                              • Sleeps 12
                                                (6)
                                                $350 - $425
                                                per night
                                                2 - 5 night minimum stay
                                                • 3 BR,
                                                • 2 BA,
                                                • Sleeps 8
                                                  (14)
                                                  2 - 7 night minimum stay
                                                  • 2 BR,
                                                  • 2 BA,
                                                  • Sleeps 4
                                                    (33)
                                                    2 - 3 night minimum stay
                                                    • 6 BR,
                                                    • 5 BA,
                                                    • 1 HF BA,
                                                    • Sleeps 12
                                                      (5)
                                                      3 - 7 night minimum stay
                                                      • 7 BR,
                                                      • 6 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 28
                                                        (7)
                                                        • 3 BR,
                                                        • 2 BA,
                                                        • Sleeps 6
                                                          (7)
                                                          2 - 7 night minimum stay
                                                          • 5 BR,
                                                          • 6 BA,
                                                          • 2 HF BA,
                                                          • Sleeps 10
                                                            (5)
                                                             

                                                            Recent Chesapeake Bay Reviews

                                                            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

                                                            Most relaxing vacation ever!

                                                            5 of 5
                                                            We were looking for a scenic, out of the way quiet vacation from a hectic life - It doesn't get any better than this! Quiet, beautiful mornings and sunsets on the deck listening to and overlooking the bay, gorgeous modern condo, (my wife LOVED the Jacuzzi tub), golf course 10 minutes up the road. Exactly what we needed. Jim was A1 as an owner, could not ask for more friendly, prompt service or replies. Thank you Jim - you definitely made our vacation tops.
                                                            • Submitted: Aug 27, 2014
                                                            • Stayed: Aug 2014

                                                            Great get away!

                                                            5 of 5
                                                            This house is just what my husband and I were looking for! Comfort and privacy with an amazing water view. The large kitchen and River Room were wonderful, as was the very spacious master bedroom with windows looking out on the Harris Creek. We spent a lot of time on the dock (reading, eating, swimming, etc.) and loved the fact that we had such a big yard with so much privacy. The house is very close to St. Michael's, where we went often for dinner, shopping, etc. during the week that we were there. We loved using the kayaks off of the dock. There were no bicycles, but I do not think that we would have wanted to bike on the busy roads anyway. Although there were just two of us, the house really has 4 bedrooms (counting the sleeping loft) and it would have easily accommodated more people. If you rent this home, you will not be sorry - it is beautiful!
                                                            • Submitted: Aug 12, 2014
                                                            • Stayed: Jul 2014