Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Bungalows
Condos
Cottages
Estates
Farmhouses
Homes
Villas
Barns
Boats
Cabins
Castles
Chalets
Hotels
Lodges
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 Long Term Vacation Rentals(104)

104 Results
2 - 3 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
    (30)
    Book it Now!
    3 - 7 night minimum stay
    • 6 BR,
    • 5 BA,
    • 1 HF BA,
    • Sleeps 18
      (16)
      2 - 3 night minimum stay
      • 6 BR,
      • 5 BA,
      • 1 HF BA,
      • Sleeps 12
        (5)
        2 night minimum stay
        • 4 BR,
        • 4 BA,
        • 1 HF BA,
        • Sleeps 10
          (3)
          • 3 BR,
          • 2 BA,
          • Sleeps 8
            (7)
            Book it Now!
            3 night minimum stay
            • 4 BR,
            • 3 BA,
            • 1 HF BA,
            • Sleeps 11
              (6)
              2 night minimum stay
              • 4 BR,
              • 4 BA,
              • Sleeps 8
                (15)
                Book it Now!
                3 night minimum stay
                • 5 BR,
                • 3 BA,
                • Sleeps 12
                  2 Reviews
                  3 - 7 night minimum stay
                  • 7 BR,
                  • 3 BA,
                  • 1 HF BA,
                  • Sleeps 18
                    (7)
                    2 - 7 night minimum stay
                    • 4 BR,
                    • 3 BA,
                    • Sleeps 8
                      1 Review
                      3 night minimum stay
                      • 5 BR,
                      • 7 BA,
                      • Sleeps 10
                        (12)
                        • 4 BR,
                        • 2 BA,
                        • 1 HF BA,
                        • Sleeps 8
                          (11)
                          2 - 7 night minimum stay
                          • 4 BR,
                          • 3 BA,
                          • Sleeps 10
                            (25)
                            Book it Now!
                            1 - 3 night minimum stay
                            • 2 BR,
                            • 1 BA,
                            • Sleeps 6
                              2 Reviews
                              2 - 3 night minimum stay
                              • 3 BR,
                              • 2 BA,
                              • 1 HF BA,
                              • Sleeps 9
                                (11)
                                Book it Now!
                                2 night minimum stay
                                • 3 BR,
                                • 2 BA,
                                • Sleeps 8
                                  (26)
                                  2 - 7 night minimum stay
                                  • 5 BR,
                                  • 4 BA,
                                  • Sleeps 10
                                    (13)
                                    2 - 3 night minimum stay
                                    • 3 BR,
                                    • 3 BA,
                                    • 1 HF BA,
                                    • Sleeps 8
                                      (12)
                                      2 - 3 night minimum stay
                                      • 4 BR,
                                      • 4 BA,
                                      • 2 HF BA,
                                      • Sleeps 10
                                        2 Reviews
                                        2 night minimum stay
                                        • 3 BR,
                                        • 3 BA,
                                        • Sleeps 6
                                          (6)
                                          3 night minimum stay
                                          • 2 BR,
                                          • 1 BA,
                                          • Sleeps 5
                                            (12)
                                            $225 - $250
                                            per night
                                            Book it Now!
                                            2 night minimum stay
                                            • 3 BR,
                                            • 2 BA,
                                            • Sleeps 10
                                              (3)
                                              Book it Now!
                                              2 night minimum stay
                                              • 3 BR,
                                              • 2 BA,
                                              • 1 HF BA,
                                              • Sleeps 9
                                                (11)
                                                $107 - $110
                                                per night
                                                Book it Now!
                                                3 - 7 night minimum stay
                                                • 3 BR,
                                                • 1 BA,
                                                • Sleeps 6
                                                  (10)
                                                  $200 - $350
                                                  per night
                                                  Book it Now!
                                                  2 night minimum stay
                                                  • 2 BR,
                                                  • 1 BA,
                                                  • 1 HF BA,
                                                  • Sleeps 8
                                                    (7)
                                                    Book it Now!
                                                    7 night minimum stay
                                                    • 4 BR,
                                                    • 2 BA,
                                                    • Sleeps 12
                                                      (4)
                                                      Book it Now!
                                                      2 night minimum stay
                                                      • 2 BR,
                                                      • 1 BA,
                                                      • Sleeps 6
                                                        (5)
                                                        2 - 6 night minimum stay
                                                        • 2 BR,
                                                        • 1 BA,
                                                        • Sleeps 5
                                                          (25)
                                                          3 night minimum stay
                                                          • 2 BR,
                                                          • 2 BA,
                                                          • Sleeps 6
                                                            (23)
                                                            Book it Now!
                                                            2 - 7 night minimum stay
                                                            • 3 BR,
                                                            • 2 BA,
                                                            • Sleeps 6
                                                              (8)
                                                               

                                                              Recent Chesapeake Bay Reviews

                                                              Shhhhh! This place is a blissfully secluded gem.

                                                              5 of 5
                                                              The owner was very responsive and helpful. The place was well maintained and clean. It was nice having the beds made on arrival. The lawn was great for games. The beach was pleasant and we all enjoyed looking for the plentiful sea glass!
                                                              • Submitted: Aug 28, 2014
                                                              • Stayed: Aug 2014

                                                              Best vacation spot on the Eastern Shore

                                                              5 of 5
                                                              This was our 5th year spending our summer family vacation on the Eastern Shore. Misbayhaven is by far the best home we have rented to date. The house is very clean and the layout is perfect. The selling feature of this house is the porch. We lived in the porch - rain or shine! The family never even sat in the living room or family room. We had 2 chefs with us and they both loved the well-stocked kitchen and all the cooking equipment. The master bedroom on the first floor was perfect for our elderly mother. Debbie, the homeowner, is great to work with and very responsive to our emails and requests. We hope to return in 2015!
                                                              • Submitted: Aug 26, 2014
                                                              • Stayed: Jul 2014

                                                              Beautiful and so peaceful

                                                              5 of 5
                                                              We had a wonderful stay at Broad Creek Lodge. The property was clean and comfortable. We had fun in the pool and the hot tub was great. However, what we enjoyed the most were the beautiful views and the peace and tranquility. We had such fun crabbing right from the dock! Having access to the bikes and kayaks made our stay perfect. Ruta from Chesapeake Bay Real Estate was very helpful in arranging our stay and in providing information about the area.
                                                              • Submitted: Aug 24, 2014
                                                              • Stayed: Aug 2014