check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!
  • Showing 1-50 of 247
Additional fees apply. Taxes may be added.
    Excellent! 4.4/5
    (28 reviews)
    avg/night
    • 6 BR
    • 3 BA
    • 1 HF BA
    • Sleeps 9
    House #198445vb
    28
    Viewed 35 times in the last 48 hours
      Wonderful! 4.9/5
      (64 reviews)
      avg/night
      • 4 BR
      • 4 BA
      • Sleeps 8
      House #432739vb
      64
      Viewed 15 times in the last 48 hours
        Wonderful! 4.9/5
        (56 reviews)
        avg/night
        • 4 BR
        • 2 BA
        • 1 HF BA
        • Sleeps 8
        House #123352
        56
        Viewed 35 times in the last 48 hours
          Wonderful! 4.8/5
          (40 reviews)
          avg/night
          • 4 BR
          • 3 BA
          • Sleeps 10
          House #40646vb
          40
          Viewed 22 times in the last 48 hours
            Excellent! 4.7/5
            (15 reviews)
            avg/night
            • 4 BR
            • 2 BA
            • Sleeps 9
            House #410948vb
            15
            Viewed 18 times in the last 48 hours
              • 4 BR
              • 3 BA
              • 1 HF BA
              • Sleeps 8
              House #391798vb
              34
                • 4 BR
                • 3 BA
                • Sleeps 10
                House #732405vb
                Viewed 13 times in the last 48 hours
                  • 4 BR
                  • 3 BA
                  • Sleeps 8
                  House #292678vb
                  1 Review
                    Wonderful! 4.8/5
                    (13 reviews)
                    avg/night
                    • 4 BR
                    • 2 BA
                    • Sleeps 6
                    House #3961324
                    13
                    Viewed 6 times in the last 48 hours
                      Exceptional! 5.0/5
                      (23 reviews)
                      avg/night
                      • 2 BR
                      • 1 BA
                      • Sleeps 5
                      House #986821
                      23
                      Viewed 22 times in the last 48 hours
                        Wonderful! 4.9/5
                        (13 reviews)
                        avg/night
                        • 5 BR
                        • 3 BA
                        • Sleeps 12
                        House #750777vb
                        13
                        Viewed 18 times in the last 48 hours
                          Exceptional! 5.0/5
                          (6 reviews)
                          avg/night
                          • 6 BR
                          • 3 BA
                          • Sleeps 12
                          House #227037vb
                          6
                          Viewed 19 times in the last 48 hours
                            • 3 BR
                            • 2 BA
                            • Sleeps 6
                            House #4108745
                            2 Reviews
                              Wonderful! 4.8/5
                              (52 reviews)
                              avg/night
                              • 4 BR
                              • 4 BA
                              • Sleeps 14
                              House #241350
                              52
                              Viewed 27 times in the last 48 hours
                                Wonderful! 4.9/5
                                (16 reviews)
                                avg/night
                                • 5 BR
                                • 4 BA
                                • Sleeps 18
                                House #581725vb
                                16
                                Viewed 16 times in the last 48 hours
                                  Exceptional! 5.0/5
                                  (9 reviews)
                                  avg/night
                                  • 4 BR
                                  • 2 BA
                                  • 1 HF BA
                                  • Sleeps 10
                                  House #803091vb
                                  9
                                  Viewed 17 times in the last 48 hours
                                    • 2 BR
                                    • 2 BA
                                    • 2 HF BA
                                    • Sleeps 6
                                    House #169544
                                    6
                                      • 3 BR
                                      • 3 BA
                                      • 1 HF BA
                                      • Sleeps 9
                                      House #3537177
                                      15
                                        Wonderful! 4.9/5
                                        (20 reviews)
                                        avg/night
                                        • 5 BR
                                        • 3 BA
                                        • Sleeps 10
                                        House #713006vb
                                        20
                                        Viewed 8 times in the last 48 hours
                                          Wonderful! 4.9/5
                                          (11 reviews)
                                          avg/night
                                          • 5 BR
                                          • 5 BA
                                          • Sleeps 12
                                          House #759930vb
                                          11
                                          Viewed 13 times in the last 48 hours
                                            Excellent! 4.7/5
                                            (19 reviews)
                                            avg/night
                                            • 5 BR
                                            • 3 BA
                                            • Sleeps 14
                                            House #617890vb
                                            19
                                            Viewed 37 times in the last 48 hours
                                              Excellent! 4.5/5
                                              (13 reviews)
                                              avg/night
                                              • 4 BR
                                              • 2 BA
                                              • Sleeps 10
                                              House #3771110
                                              13
                                              Viewed 5 times in the last 48 hours
                                                Wonderful! 4.9/5
                                                (7 reviews)
                                                avg/night
                                                • 6 BR
                                                • 4 BA
                                                • 2 HF BA
                                                • Sleeps 14
                                                House #3926292
                                                7
                                                Viewed 14 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (48 reviews)
                                                  avg/night
                                                  • 4 BR
                                                  • 3 BA
                                                  • Sleeps 12
                                                  House #168663vb
                                                  48
                                                  Viewed 52 times in the last 48 hours
                                                    Exceptional! 5.0/5
                                                    (40 reviews)
                                                    avg/night
                                                    • 3 BR
                                                    • 3 BA
                                                    • Sleeps 8
                                                    House #294688vb
                                                    40
                                                    Viewed 28 times in the last 48 hours
                                                      Exceptional! 5.0/5
                                                      (78 reviews)
                                                      avg/night
                                                      • 3 BR
                                                      • 3 BA
                                                      • 1 HF BA
                                                      • Sleeps 10
                                                      House #432131vb
                                                      78
                                                        Wonderful! 4.8/5
                                                        (14 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 3 BA
                                                        • Sleeps 8
                                                        House #60381vb
                                                        14
                                                        Viewed 23 times in the last 48 hours
                                                          Exceptional! 5.0/5
                                                          (9 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 6
                                                          House #4176147
                                                          9
                                                          Viewed 15 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (31 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 1 BA
                                                            • 1 HF BA
                                                            • Sleeps 5
                                                            House #209767vb
                                                            31
                                                            Viewed 8 times in the last 48 hours
                                                              • 3 BR
                                                              • 2 BA
                                                              • 2 HF BA
                                                              • Sleeps 10
                                                              House #989211
                                                              18
                                                                • 3 BR
                                                                • 4 BA
                                                                • 1 HF BA
                                                                • Sleeps 8
                                                                House #3943466
                                                                8
                                                                Viewed 10 times in the last 48 hours
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 6
                                                                  House #731347vb
                                                                  22
                                                                    Wonderful! 4.9/5
                                                                    (13 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 8
                                                                    House #833414vb
                                                                    13
                                                                    Viewed 9 times in the last 48 hours
                                                                      Excellent! 4.7/5
                                                                      (28 reviews)
                                                                      avg/night
                                                                      • 4 BR
                                                                      • 4 BA
                                                                      • Sleeps 12
                                                                      House #472869vb
                                                                      28
                                                                      Viewed 20 times in the last 48 hours
                                                                        Exceptional! 5.0/5
                                                                        (8 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 6
                                                                        House #4069765
                                                                        8
                                                                        Viewed 12 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (19 reviews)
                                                                          avg/night
                                                                          • 3 BR
                                                                          • 1 BA
                                                                          • Sleeps 6
                                                                          House #429964vb
                                                                          19
                                                                          Viewed 16 times in the last 48 hours
                                                                            Exceptional! 5.0/5
                                                                            (23 reviews)
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 8
                                                                            House #684953vb
                                                                            23
                                                                            Viewed 15 times in the last 48 hours
                                                                              Very Good! 4.0/5
                                                                              (11 reviews)
                                                                              $87
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 6
                                                                              House #583519vb
                                                                              11
                                                                              Viewed 8 times in the last 48 hours
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 6
                                                                                House #707088vb
                                                                                1 Review
                                                                                  Exceptional! 5.0/5
                                                                                  (30 reviews)
                                                                                  avg/night
                                                                                  • 4 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 12
                                                                                  House #371050vb
                                                                                  30
                                                                                  Viewed 17 times in the last 48 hours
                                                                                    avg/night
                                                                                    • 4 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 10
                                                                                    House #807108vb
                                                                                    2 Reviews
                                                                                    Viewed 12 times in the last 48 hours
                                                                                      Wonderful! 4.9/5
                                                                                      (11 reviews)
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 4 BA
                                                                                      • Sleeps 8
                                                                                      House #758368vb
                                                                                      11
                                                                                        Excellent! 4.7/5
                                                                                        (6 reviews)
                                                                                        avg/night
                                                                                        • 4 BR
                                                                                        • 3 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 10
                                                                                        House #655263vb
                                                                                        6
                                                                                        Viewed 24 times in the last 48 hours
                                                                                          • 5 BR
                                                                                          • 4 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 12
                                                                                          House #675274vb
                                                                                          13
                                                                                            Wonderful! 4.8/5
                                                                                            (12 reviews)
                                                                                            avg/night
                                                                                            • 4 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 9
                                                                                            House #3895721
                                                                                            12
                                                                                            Viewed 7 times in the last 48 hours
                                                                                              Excellent! 4.6/5
                                                                                              (30 reviews)
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 12
                                                                                              House #7002752
                                                                                              30
                                                                                              Viewed 29 times in the last 48 hours
                                                                                                Exceptional! 5.0/5
                                                                                                (8 reviews)
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 11
                                                                                                House #743272vb
                                                                                                8
                                                                                                Viewed 5 times in the last 48 hours
                                                                                                  Exceptional! 5.0/5
                                                                                                  (86 reviews)
                                                                                                  avg/night
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 9
                                                                                                  House #131054vb
                                                                                                  86
                                                                                                  Viewed 12 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (10 reviews)
                                                                                                    avg/night
                                                                                                    • 4 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 10
                                                                                                    House #398147vb
                                                                                                    10
                                                                                                    Viewed 18 times in the last 48 hours
                                                                                                      Wonderful! 4.9/5
                                                                                                      (7 reviews)
                                                                                                      avg/night
                                                                                                      • 4 BR
                                                                                                      • 3 BA
                                                                                                      • Sleeps 10
                                                                                                      House #761352vb
                                                                                                      7
                                                                                                      Viewed 5 times in the last 48 hours
                                                                                                      • 1 - 50 of 247

                                                                                                      St. Michaels: House Rentals (247)

                                                                                                       

                                                                                                      Recent St. Michaels Reviews

                                                                                                      Plenty of room, neat and functional with lots of interesting handiwork and creative decor

                                                                                                      5 of 5
                                                                                                      Allegra met us at the house and was very friendly. We were met by a basket of goodies (for me that's locally blended coffee) and a bottle of wine. We had everything we needed or wanted. Great house.
                                                                                                      • Submitted: Nov 27, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Beautiful property and view!

                                                                                                      5 of 5
                                                                                                      This is a review I meant to submit 2 years ago - it didn't go through correctly which I realized as I eagerly booked our next stay at this wonderful spot. Looking forward to it! Here is the review from our last stay: "We had 6 adults and 2 kids sleep very comfortably in this beautiful property. The views are just incredible, the kitchen was very well-stocked with supplies (we cook a lot) and there were two comfortable sitting areas to read and relax (one with a fireplace.) We had a great 4 days there for our family get away and hope to return again! Lisa was wonderful to work with and very responsive. The Chesapeake Maritime Museum is well worth a visit!"
                                                                                                      • Submitted: Nov 13, 2016
                                                                                                      • Stayed: Nov 2016

                                                                                                      Amazing

                                                                                                      5 of 5
                                                                                                      Loved the cabin and the area. We are already planning a trip back in the near future. Very suitable for what we wanted. Not a far walk to the beaches and beautiful views.
                                                                                                      • Submitted: Nov 9, 2016
                                                                                                      • Stayed: Nov 2016