Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Chestertown: Houses, Estates & More(23)

23 Results
2 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 8
    (15)
    Book it Now!
    90 night minimum stay
    • 4 BR,
    • 4 BA,
    • 1 HF BA,
    • Sleeps 8
      Book it Now!
      2 night minimum stay
      • 3 BR,
      • 2 BA,
      • 1 HF BA,
      • Sleeps 6
        Book it Now!
        2 night minimum stay
        • 3 BR,
        • 2 BA,
        • 1 HF BA,
        • Sleeps 9
          2 Reviews
          Book it Now!
          • 2 BR,
          • 1 BA,
          • 1 HF BA,
          • Sleeps 4
            3 - 7 night minimum stay
            • 5 BR,
            • 2 BA,
            • 1 HF BA,
            • Sleeps 10
              $140 - $205
              per night
              2 night minimum stay
              • 3 BR,
              • 1 BA,
              • 1 HF BA,
              • Sleeps 7
                (15)
                2 night minimum stay
                • 3 BR,
                • 1 BA,
                • Sleeps 6
                  (13)
                  $250 - $270
                  per night
                  Book it Now!
                  3 night minimum stay
                  • 2 BR,
                  • 1 BA,
                  • 1 HF BA,
                  • Sleeps 4
                    (4)
                    2 night minimum stay
                    • 2 BR,
                    • 1 BA,
                    • 1 HF BA,
                    • Sleeps 6
                      (12)
                      Book it Now!
                      2 - 3 night minimum stay
                      • 2 BR,
                      • 1 BA,
                      • Sleeps 5
                        2 night minimum stay
                        • 2 BR,
                        • 2 BA,
                        • Sleeps 3
                          (8)
                          Book it Now!
                          • 1 BR,
                          • 1 BA,
                          • Sleeps 4
                            • 1 BR,
                            • 1 BA,
                            • Sleeps 5
                              (6)
                              $1,571 - $2,998
                              per night
                              2 night minimum stay
                              • 11 BR,
                              • 8 BA,
                              • 1 HF BA,
                              • Sleeps 27
                                1 Review
                                • 4 BR,
                                • 3 BA,
                                • 1 HF BA,
                                • Sleeps 10
                                  1 Review
                                  3 night minimum stay
                                  • 5 BR,
                                  • 2 BA,
                                  • Sleeps 14
                                    2 night minimum stay
                                    • 3 BR,
                                    • 4 BA,
                                    • 1 HF BA,
                                    • Sleeps 7
                                      (16)
                                      • 4 BR,
                                      • 2 BA,
                                      • 1 HF BA,
                                      • Sleeps 9
                                        • 4 BR,
                                        • 2 BA,
                                        • Sleeps 12
                                          • 4 BR,
                                          • Sleeps 12
                                            1 Review
                                            • 5 BR,
                                            • 3 BA,
                                            • 1 HF BA,
                                            • Sleeps 15
                                              1 Review
                                              Advertisement