Chestertown hotels

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Best Chestertown hotels

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$0 - $53$53 - $106$106 - $159$159 - $211$211+ per night

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Most recommended Chestertown hotels

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Driftwood Inn - Chestertown - Bedroom
Driftwood Inn
Chestertown, MD
4.9Mediocre(163)
Parking
Free Wi-Fi
Pet friendly
$69+
Check availability
Red Roof Inn & Suites Chestertown - Chestertown - Bedroom
Red Roof Inn & Suites Chestertown
Chestertown, MD
6.9Okay(35)
Free Wi-Fi
Pet friendly
$101+
Check availability
Comfort Inn and Suites Chestertown - Chestertown - Living room
Comfort Inn and Suites Chestertown
Chestertown, MD
8.0Very good(234)
Parking
Free Wi-Fi
Pool
Pet friendly
$139+
Check availability
Great Oak Manor - Chestertown
Great Oak Manor
Chestertown, MD
9.3Wonderful(63)
Free Wi-Fi
$165+
Check availability
Inn At Mitchell House - Chestertown
Inn At Mitchell House
Chestertown, MD
Free Wi-Fi
$166+
Check availability
John L Stam House - Chestertown
John L Stam House
Chestertown, MD
Free Wi-Fi
$211+
Check availability
The Lodge at Great Oak Landing - Chestertown - Building
The Lodge at Great Oak Landing
Chestertown, MD
$257+
Check availability
Cottage within walking distance to the Bay! - Chestertown - Living room
Cottage within walking distance to the Bay!
Chestertown, MD
$329+
Check availability
Brampton 1860 - Chestertown
Brampton 1860
Chestertown, MD
9.7Wonderful(41)
Parking
Free Wi-Fi
$361+
Check availability
Historic downtown Chestertown Home. #1 Location. - Chestertown
Historic downtown Chestertown Home. #1 Location.
Chestertown, MD
Free Wi-Fi
$376+
Check availability
Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities - Chestertown
Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
Chestertown, MD
Free Wi-Fi
Pet friendly
$563+
Check availability
Private Waterfront Paradise W/ Pier - Kayak To Historic Chestertown! - Chestertown - Outdoors view
Private Waterfront Paradise W/ Pier - Kayak To Historic Chestertown!
Chestertown, MD
Free Wi-Fi
Pet friendly
$590+
Check availability
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown - Chestertown - Restaurant
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
Chestertown, MD
Spa
$717+
Check availability
River Lodge, Casual Riverfront setting - Chestertown - Building
River Lodge, Casual Riverfront setting
Chestertown, MD
Free Wi-Fi
Pet friendly
$896+
Check availability
Historic Stepne Manor on Maryland's Eastern Shore - Chestertown - Living room
Historic Stepne Manor on Maryland's Eastern Shore
Chestertown, MD
Pet friendly
$1,241+
Check availability
Historic Manor House on Beautiful Eastern Shore Estate - Chestertown - Living room
Historic Manor House on Beautiful Eastern Shore Estate
Chestertown, MD
Free Wi-Fi
Pool
Pet friendly
$1,358+
Check availability

Popular filters in Chestertown hotels

Hotels with parking
Comfort Inn and Suites Chestertown and others
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Useful Info

KAYAK’s insights for hotels in Chestertown

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Chestertown with confidence.

Which month has the cheapest hotel rates in Chestertown?

Hotels are cheapest in Chestertown in January, with average rates of $92. In comparison, September is the most expensive month, with prices at $248.

What is the cheapest day of the week to book a hotel in Chestertown?

Tuesday offers the lowest rates in Chestertown, with an average nightly price of $122. The highest prices are found on Thursday, with average rates at $310.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

February
September
$100
$157
Cheapest month to stay with an average 35% drop in price.
Most expensive month to stay with an average 51% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Chestertown hotel deals

  • If you’re looking for a cheap hotel in Washington, D.C., you should consider visiting during the low season. You'll find cheaper hotels in Washington, D.C. in January and March.
  • Hotel room prices vary depending on many factors but you’ll most likely find the best hotel deals in Washington, D.C. if you stay on a Monday. The opposite is true for, Friday, which is usually the most expensive day.
  • How long should you stay? KAYAK users usually book their hotel in Washington, D.C. for 1 day.

FAQs when booking a hotel in Chestertown

  • What are the best hotels near Chestertown Railroad Station?

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

  • 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.

Everything you need to know for your stay in Chestertown

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