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Holiday rentals in Chestertown, Maryland

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Chestertown, United States
7 May — 8 May2
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Other accommodations in Chestertown, MD

Find the perfect holiday rental for your stay in Chestertown, MD. There are 42 hotels in Chestertown, MD and price data was last updated on 30 April 2025. The average price for a hotel in Chestertown, MD is .
Show all 42 stays
Brampton 1860
Brampton 1860

Brampton 1860

25227 Chestertown Road, Chestertown, MD, United States
2.5 km from city centre
Free Wi-Fi
Air conditioning
S$ 402
Avg. per night
View Deal
Driftwood Inn
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States
1.5 km from city centre
Free Wi-Fi
Parking
S$ 90
Avg. per night
View Deal

Where to stay in Chestertown, MD

Explore different neighbourhoods and areas within Chestertown to find the perfect location for your stay. Map data was last updated on 30 April 2025.
Whether you're visiting Chestertown for leisure or business, utilize the map to find vacation rentals close to your ideal location. Clicking on a vacation rental name will take you to a page with pricing, reviews, and more useful information.

Facts about staying in Chestertown, MD

Find useful tips and insights about staying in Chestertown to help you make the most of your experience. FAQs were last updated on 30 April 2025.

  • How much does a holiday rental in Chestertown cost?

    On average, it costs S$ 418 per night for a Chestertown holiday rental, but S$ 374 per night or less would be considered a good deal. The cheapest holiday rental price our users have found recently in Chestertown was for S$ 157 per night. If you can, try to avoid booking your rental January (as this is the most expensive month). Booking March (the cheapest month) may end up saving you money.

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