Insights
Cheapest hotels

Hotels in Chestertown, Maryland

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

...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.

Customise 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 our HotelsCombined data-powered tips to help you find your next hotel in Chestertown.

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

The cheapest month to book a hotel in Chestertown is July (£65). Conversely, the most expensive month to stay in Chestertown is December (£196).

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

The cheapest day to stay in Chestertown is Sunday (£64). On the other hand, travellers can expect to pay the most on Saturday, when the average nightly price is £168.

How far ahead should you book a hotel in Chestertown?

Save money by booking a hotel at least 12 days before your trip to Chestertown. The lowest price found when booking 12 days ahead was £53 per night.

Find deals

Cheapest hotels in Chestertown, MD

At the moment, these hotels offer the lowest nightly rate out of those we've come across in Chestertown. Prices will typically fluctuate depending on the dates selected, star rating of hotel, and hotel location.
Driftwood Inn
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States
1.0 mi from city centre
Free Wi-Fi
Parking
£51
Avg. per night
View deal

Facts about staying in Chestertown, MD

  • What are the best hotels in Chestertown?

    Comfort Inn and Suites Chestertown is a very popular hotel in Chestertown, with a score of 8.1 from 293 reviews. Brampton 1860 (9.2 from 39 reviews) and First Floor Studio Apartment in Historic Chestertown (9.5 from 105 reviews) are also highly rated Chestertown hotels based on recent feedback from HotelsCombined users.

  • How much is a cheap hotel in Chestertown?

    Prices for Chestertown hotels have been found for as low as £51/night over the last 3 days. Prices for this weekend in Chestertown start from £102 per night when checking in on 23 Oct and out on 25 Oct.

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

    In addition to Chestertown, travellers opt to visit Baltimore when visiting Maryland. Ocean City is also a popular choice to visit.

  • How many hotels are there in Chestertown?

    In total, there are 49 hotels to choose from in Chestertown, compared to 11,705 properties in Maryland.

See more FAQs

Find better results for your stay in Chestertown, MD

Consider alternative stays in Chestertown

Holiday rentals in Chestertown, Maryland