Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartment
Bungalow
Condo
Cottage
Estate
Homes
Homes
Lodge
Villa
Barn
Boat
Cabin
Castle
Chalet
Hotel
Studio
Townhome
Yacht

Location Type

Even More Filters

Features

Managed By

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

Chesapeake Bay Golf Vacation Home Rentals(123)

123 Results
3 - 7 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 10
    (23)
    2 - 3 night minimum stay
    • 4 BR,
    • 2 BA,
    • Sleeps 8
      (39)
      2 - 3 night minimum stay
      • 4 BR,
      • 2 BA,
      • 1 HF BA,
      • Sleeps 8
        (30)
        2 - 3 night minimum stay
        • 7 BR,
        • 5 BA,
        • 1 HF BA,
        • Sleeps 22
          (41)
          2 - 7 night minimum stay
          • 4 BR,
          • 3 BA,
          • 1 HF BA,
          • Sleeps 10
            (14)
            2 - 3 night minimum stay
            • 5 BR,
            • 4 BA,
            • 1 HF BA,
            • Sleeps 13
              (20)
              2 - 3 night minimum stay
              • 7 BR,
              • 7 BA,
              • 1 HF BA,
              • Sleeps 22
                (15)
                2 - 3 night minimum stay
                • 3 BR,
                • 2 BA,
                • Sleeps 8
                  (31)
                  2 - 3 night minimum stay
                  • 4 BR,
                  • 3 BA,
                  • Sleeps 8
                    (16)
                    2 - 7 night minimum stay
                    • 5 BR,
                    • 5 BA,
                    • Sleeps 12
                      (13)
                      Book it Now!
                      3 - 7 night minimum stay
                      • 4 BR,
                      • 2 BA,
                      • Sleeps 9
                        (22)
                        $350 - $450
                        per night
                        Book it Now!
                        2 - 5 night minimum stay
                        • 3 BR,
                        • 2 BA,
                        • Sleeps 8
                          (14)
                          2 - 3 night minimum stay
                          • 4 BR,
                          • 4 BA,
                          • Sleeps 10
                            (8)
                            3 - 7 night minimum stay
                            • 4 BR,
                            • 4 BA,
                            • Sleeps 8
                              (30)
                              3 - 7 night minimum stay
                              • 6 BR,
                              • 5 BA,
                              • 1 HF BA,
                              • Sleeps 12
                                (5)
                                3 - 7 night minimum stay
                                • 5 BR,
                                • 3 BA,
                                • 1 HF BA,
                                • Sleeps 18
                                  (9)
                                  3 - 7 night minimum stay
                                  • 4 BR,
                                  • 3 BA,
                                  • 1 HF BA,
                                  • Sleeps 8
                                    2 Reviews
                                    3 night minimum stay
                                    • 3 BR,
                                    • 2 BA,
                                    • Sleeps 6
                                      2 Reviews
                                      Book it Now!
                                      3 night minimum stay
                                      • 4 BR,
                                      • 3 BA,
                                      • 1 HF BA,
                                      • Sleeps 11
                                        (5)
                                        2 - 7 night minimum stay
                                        • 3 BR,
                                        • 2 BA,
                                        • Sleeps 8
                                          (11)
                                          2 - 7 night minimum stay
                                          • 4 BR,
                                          • 3 BA,
                                          • Sleeps 8
                                            1 Review
                                            3 - 7 night minimum stay
                                            • 6 BR,
                                            • 3 BA,
                                            • Sleeps 12
                                              (3)
                                              2 - 7 night minimum stay
                                              • 3 BR,
                                              • 2 BA,
                                              • Sleeps 9
                                                1 Review
                                                2 - 7 night minimum stay
                                                • 4 BR,
                                                • 3 BA,
                                                • Sleeps 10
                                                  (25)
                                                  2 - 4 night minimum stay
                                                  • 5 BR,
                                                  • 3 BA,
                                                  • Sleeps 9
                                                    2 Reviews
                                                    2 - 4 night minimum stay
                                                    • 4 BR,
                                                    • 2 BA,
                                                    • 1 HF BA,
                                                    • Sleeps 12
                                                      (25)
                                                      Book it Now!
                                                      2 night minimum stay
                                                      • 3 BR,
                                                      • 2 BA,
                                                      • Sleeps 8
                                                        (26)
                                                        • 4 BR,
                                                        • 2 BA,
                                                        • Sleeps 10
                                                          (7)
                                                          2 - 7 night minimum stay
                                                          • 5 BR,
                                                          • 4 BA,
                                                          • Sleeps 10
                                                            (12)
                                                             

                                                            Recent Chesapeake Bay Reviews

                                                            FANTASTIC! Hard to leave this beautiful oasis!

                                                            5 of 5
                                                            Misbayhaven was the perfect house for our getaway with another couple even though it can accommodate large groups. Loved the beautiful decor of the house and the view was picture perfect as well as the sunsets. We had a fun evening watching a massive thunderstorm from the comfortably appointed sunroom after cooking a great meal in the well designed kitchen offering us cooks limitless tools of the trade!!! The bedrooms had wonderful linens and very comfortable. The pool and hot tub were super clean and perfect for hot summer days! Deb was a godsend and was great in responding and following up to make sure our trip was wonderful. Easy car ride to town and great restaurants - loved 208 Talbot, Gina's for margaritas and lunch, and the Crab Claw for the best Maryland Crab soup! A home run! We look forward to returning!!!
                                                            • Submitted: Jul 29, 2014
                                                            • Stayed: Jul 2014

                                                            This is a wonderful home that has the most beautiful 7 acre waterfront property I have ever seen

                                                            5 of 5
                                                            May family and I had a wonderful week. The home is comfortable and spotless, the pool is wonderful, the grounds are spectacular and the fishing is the BEST! We have made it a semi annual trip we count on.
                                                            • Submitted: Feb 24, 2014
                                                            • Stayed: Jun 2013

                                                            Just what we were hoping for - and needed!

                                                            5 of 5
                                                            This is such a lovely home - it has aged so gracefully and yet retains all of the charm that you rarely see in houses today. My husband and I (and our two rambunctious young dogs) couldn't have asked for a better place to stay. The house is comfortable and beautiful - the kitchen is a dream (extremely well-equipped) and the Master suite even better; I loved waking up and walking right out onto the deck overlooking the river. The listing is not only accurate, I felt it didn't quite do the place justice! The one bedroom not pictured is just gorgeous. We felt like we had a fancy B&B for our private use. The linens provided were great - towels were plentiful and high quality. The home is spacious and the site is private - yet everything you could want (supermarket, convenience store, museums, restaurants) is so close and the drive to them couldn’t be easier. St. Michaels is charming and a lot of fun to walk through – very dog friendly, too. If you bring your pups make sure you take them to Flying Fred’s pet shop for treats and petting. You can even eat on Ava's Pizzeria & Wine Bar patio with them and they have a dog’s menu. We had our Anniversary dinner at 208 Talbot and it was everything TripAdvisor had promised. Lisa (the owner) was very easy to communicate with and very hospitable – she even left dishes and leashes for the dogs! We got our security deposit refunded promptly – which has not always been our experience. When we come back to St. Michaels – and we will – we wouldn’t consider staying anywhere but Cranford.
                                                            • Submitted: Oct 29, 2013
                                                            • Stayed: Oct 2013