Holiday rentals in Chestertown, Maryland

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Other accommodations in Chestertown, MD

Find the perfect holiday rental for your stay in Chestertown, MD. There are 43 hotels in Chestertown, MD and price data was last updated on 28 January 2026. The average price for a hotel in Chestertown, MD is .
Driftwood Inn
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States
1.5 km from city centre
Free Wi-Fi
Parking
S$ 87
Avg. per night
View Deal

Where to stay in Chestertown

Explore different neighbourhoods and areas within Chestertown, MD to find the perfect location for your stay. Map data was last updated on 28 January 2026.
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 28 January 2026.

  • How much does a holiday rental in Chestertown cost?

    On average, it costs S$ 382 per night for a Chestertown holiday rental, but S$ 357 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$ 143 per night. If you can, try to avoid booking your rental August (as this is the most expensive month). Booking December (the cheapest month) may end up saving you money.

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