Holiday Homes in Chestertown
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Our top choices for Chestertown holiday homes
Amazing Modern house with a full kitchen and parking
Amazing Modern house with a full kitchen and parkingSmyrna
9.2 out of 10, Wonderful, (10 reviews)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
Laurie S.
The price is AU$403
includes taxes & fees
4 May - 5 May
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 AU$578
includes taxes & fees
4 May - 5 May
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 AU$366
includes taxes & fees
4 May - 5 May
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 AU$458
includes taxes & fees
30 Apr - 1 May
Adorable two-bedroom retreat close to Easton, Denton, Centreville
Adorable two-bedroom retreat close to Easton, Denton, CentrevilleQueen Anne
10.0 out of 10, Exceptional, (28 reviews)
"Really cute little place - very clean and owners are great about checking in on you to make sure things are great."
Cheryl
The price is AU$481
includes taxes & fees
10 May - 11 May
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 AU$497
includes taxes & fees
19 May - 20 May
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 AU$391
includes taxes & fees
7 May - 8 May
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 AU$575
includes taxes & fees
27 May - 28 May
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 | 582 |
|---|---|
Accommodation | 411 Holiday Homes |
Lowest Price | AU$255 |
Highest Price | AU$981 |