Holiday Homes in Chestertown
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Our top choices for Chestertown holiday homes
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Relax on Kent Island in a 4 Bedroom Home w/Waterview!Stevensville
9.8 out of 10, Exceptional, (43 reviews)
"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"
Supriya V.
The price is NZ$399
includes taxes & fees
19 Apr - 20 Apr
Charming Coastal/Country Home w/3 Acres & Sauna!
Charming Coastal/Country Home w/3 Acres & Sauna!Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great stay, would do it again."
Brandon D.
The price is NZ$421
includes taxes & fees
20 Apr - 21 Apr
Boho Oasis 2 Bed 1 Bath home in Baltimore City!
Boho Oasis 2 Bed 1 Bath home in Baltimore City!Berea
9.8 out of 10, Exceptional, (6 reviews)
"House kept very clean and neighborhood was really quiet at night! Will be staying again."
Pai’Syn
The price is NZ$477
includes taxes & fees
19 Apr - 20 Apr
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.Grasonville
9.6 out of 10, Exceptional, (12 reviews)
"Great overnight stay for a wedding nearby. Would highly recommend!"
Kevin F.
The price is NZ$705
includes taxes & fees
20 Apr - 21 Apr
Large 2 bedroom house with private parking in a nice neighborhood
Large 2 bedroom house with private parking in a nice neighborhoodArnold
9.4 out of 10, Exceptional, (38 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
Traci L.
The price is NZ$553
includes taxes & fees
20 Apr - 21 Apr
Hidden Fells Point Gem / Private Courtyard Patio
Hidden Fells Point Gem / Private Courtyard PatioFells Point
9.6 out of 10, Exceptional, (95 reviews)
"Awesome place, great location"
Mark M.
The price is NZ$341
includes taxes & fees
29 Apr - 30 Apr
Bayside Cottage steps from Rock Hall Harbor
Bayside Cottage steps from Rock Hall HarborRock Hall
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
Dorothy R.
The price is NZ$614
includes taxes & fees
4 May - 5 May
Charming 2-bedroom house in Aberdeen with WiFi and AC
Charming 2-bedroom house in Aberdeen with WiFi and ACAberdeen
7.8 out of 10, Good, (14 reviews)
"Met our needs. Great stay."
Robert C.
The price is NZ$157
includes taxes & fees
24 Apr - 25 Apr
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chestertown Hotel Reviews
Historic Inns of Annapolis
10/10 Excellent
Find out more about Chestertown
Chestertown Holiday Homes information
Number of reviews | 536 |
|---|---|
Accommodation | 453 Holiday Homes |
Lowest Price | NZ$157 |
Highest Price | NZ$1,992 |