Chestertown hotels

Sat 4/20
Wed 4/24

Search hundreds of travel sites at once for hotels in Chestertown, Maryland

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Bundle and saveSave money when you bundle your flight + hotel.

Best Chestertown hotels

Most recommended Chestertown hotels

Show all
Comfort Inn and Suites Chestertown - Chestertown - Lounge
Parking
Free Wi-Fi
Pet friendly
Red Roof Inn & Suites Chestertown - Chestertown - Bedroom
Free Wi-Fi
Pet friendly
Driftwood Inn
5.8 Fair
$78+
$78+
Parking
Free Wi-Fi
Pet friendly

Good to know

Low season

January

High season

September

Average price (weeknight)

$121

Average price (weekend night)

$167
Cheapest month to stay with an average 41% drop in price.
Most expensive month to stay with an average 29% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

When to book a hotel in Chestertown

Price per night / 3-star hotel. Prices are not fixed and may vary with time.
Average nightly price per month
Average nightly price

Top tips for finding Chestertown hotel deals

  • If you’re looking for a cheap hotel in Chestertown, you should consider visiting during the low season. You'll find cheaper hotels in Chestertown in January and December.
  • Hotel room prices vary depending on many factors but you’ll most likely find the best hotel deals in Chestertown if you stay on a Saturday. The opposite is true for, Thursday, which is usually the most expensive day.
  • Book at least 68 days before your stay begins to get the best price for your Chestertown hotel.
  • The cheapest 3-star hotel room in Chestertown found on KAYAK in the last 2 weeks was $97, while the most expensive was $97.
  • How long should you stay? KAYAK users usually book their hotel in Chestertown for 1 day.

FAQs when booking a hotel in Chestertown

  • What are the best hotels near Chestertown Railroad Station?

    Comfort Inn and Suites Chestertown and Driftwood Inn are very popular with users who want to stay within walking distance of Chestertown Railroad Station.

  • How much does a hotel cost in Chestertown?

    In the last 3 days, double rooms in Chestertown have been found on KAYAK for as cheap as $111. On average, the price for a double room is $142.

  • Which amenities do KAYAK users look for when booking a hotel in Chestertown?

    The most sought-after amenity KAYAK users looked for in their hotel in Chestertown is: pet friendly.

  • How do I find a hotel in central Chestertown?

    After you launch a hotel search on KAYAK, you can refine your research by neighborhood, which allows you to pick the central Chestertown districts. You can also do a search using the city map to choose a specific location, like Chestertown city center.

  • How can I find hotels near me?

    Take a look at our extensive hotel map to find the best hotels near you.

Where to stay in Chestertown?

Our map will help you find the perfect place to stay in Chestertown by showing you the exact location of each hotel.