Insights
Cheapest hotels

Hotels in Chestertown, Maryland

Search and compare Chestertown, Maryland hotels from hundreds of travel sites on HotelsCombined and save.

Chestertown, United States
7 May — 8 May2
...and more

Learn why travellers love HotelsCombined

Compare hotel ratings collected from thousands of user reviews.

One search gives you accurate pricing on affordable hotels.

Customie your results by hotel chain, amenities, price and more.

Search for hotels as many times as you want – for free.

Travel insights for hotels in Chestertown

Use these up-to-date, data-driven insights about booking a hotel in Chestertown including ideal times to book, pricing trends, and more.

What is the cheapest month to book a hotel in Chestertown?

The cheapest month to book a hotel in Chestertown is January (S$ 158). Conversely, the most expensive month to stay in Chestertown is September (S$ 373).

What is the cheapest day to stay in a hotel in Chestertown?

The cheapest day to stay in Chestertown is Tuesday (S$ 167). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is S$ 582.
Find deals

Cheapest hotels in Chestertown, MD

Discover affordable stays in Chestertown, MD that provide a quality experience without breaking the bank. Hotels in Chestertown, MD can be found for as low as S$ 90 per night. There is currently one property in Chestertown, MD that can be booked for this price. Driftwood Inn is one of the hotels that can be booked for the lowest price in Chestertown, MD. Price data was last updated on 30 April 2025
These are the lowest prices we've found on hotels in Chestertown at the moment. As prices can vary by date, change the dates if you're flexible to compare rates.
Show all 42 hotels
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
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

Other accommodations in Chestertown, MD

Find the perfect hostel, theme hotel, or holiday rental for your stay in Chestertown, MD.
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

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.

  • What are the best hotels in Chestertown?

    One of the most popular hotels in Chestertown is Comfort Inn and Suites Chestertown, which has been reviewed by 220 users and currently has a rating of 7.9/10. Other top-rated locations include Red Roof Inn & Suites Chestertown and Brampton 1860, which have received 7.2/10 and 9.4/10 ratings from our users, respectively.

  • How much is a cheap hotel in Chestertown?

    HotelsCombined users have found cheap hotels in Chestertown starting from S$ 89 per night in the last 3 days.

  • What are some other cities to stay in when visiting Maryland?

    In addition to Chestertown, travellers opt to visit Bethesda when visiting Maryland.

  • How many hotels are there in Chestertown?

    In total, there are 42 hotels to choose from in Chestertown, compared to 14,096 properties in Maryland.

See more FAQs

Find better results for your stay in Chestertown, MD

Consider alternative stays in Chestertown

If you are looking for a specific type of hotel, consider these options for trips to Chestertown
Holiday rentals in Chestertown, Maryland