Chestertown hotels

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Best Chestertown hotels

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Most recommended Chestertown hotels

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Red Roof Inn & Suites Chestertown - Chestertown - Bedroom
Red Roof Inn & Suites Chestertown
Chestertown, MD, United States
7.2Good(32)
Free Wi-Fi
Pet-friendly
$151+
View availability
Comfort Inn and Suites Chestertown - Chestertown - Living room
Comfort Inn and Suites Chestertown
Chestertown, MD, United States
7.9Good(220)
Parking
Free Wi-Fi
Pet-friendly
$251+
View availability
Cottage within walking distance to the Bay! - Chestertown - Living room
Cottage within walking distance to the Bay!
Chestertown, MD, United States
$514+
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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, United States
Free Wi-Fi
Pet-friendly
$867+
View availability
Private Waterfront Paradise W/ Pier - Kayak To Historic Chestertown! - Chestertown - Outdoor view
Private Waterfront Paradise W/ Pier - Kayak To Historic Chestertown!
Chestertown, MD, United States
Free Wi-Fi
Pet-friendly
$917+
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Historic Downtown Garden Oasis with Private Patio - Chestertown - Patio
Historic Downtown Garden Oasis with Private Patio
Chestertown, MD, United States
Free Wi-Fi
$467+
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Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown - Chestertown - Restaurant
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
Chestertown, MD, United States
Spa
$1,132+
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Historic Manor House on Beautiful Eastern Shore Estate - Chestertown - Living room
Historic Manor House on Beautiful Eastern Shore Estate
Chestertown, MD, United States
Free Wi-Fi
Pool
Pet-friendly
$2,362+
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River Lodge, Casual Riverfront setting - Chestertown - Building
River Lodge, Casual Riverfront setting
Chestertown, MD, United States
Free Wi-Fi
Pet-friendly
$1,399+
View availability
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest - Chestertown - Living room
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Chestertown, MD, United States
Free Wi-Fi
$514+
View availability
Historic Stepne Manor on Maryland's Eastern Shore - Chestertown - Living room
Historic Stepne Manor on Maryland's Eastern Shore
Chestertown, MD, United States
Pet-friendly
$1,938+
View availability
John L Stam House - Chestertown
John L Stam House
Chestertown, MD, United States
Free Wi-Fi
$329+
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Inn At Mitchell House - Chestertown
Inn At Mitchell House
Chestertown, MD, United States
Free Wi-Fi
$259+
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Beautiful home for a family vacation - Chestertown
Beautiful home for a family vacation
Chestertown, MD, United States
Free Wi-Fi
Pet-friendly
$1,063+
View availability
Great Oak Manor - Chestertown
Great Oak Manor
Chestertown, MD, United States
9.3Wonderful(63)
Free Wi-Fi
$258+
View availability
First Time Vrbo Offering! - Chestertown
First Time Vrbo Offering!
Chestertown, MD, United States
$798+
View availability

Popular amenities in Chestertown hotels

Hotels with parking
Comfort Inn and Suites Chestertown and others
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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 $225. In comparison, September is the most expensive month, with prices at $531.

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 $238. The highest prices are found on Friday, with average rates at $828.
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Good to know

Low season

January

High season

September

Average price (weeknight)

$262

Average price (weekend night)

$448
Cheapest month to stay with an average 38% drop in price.
Most expensive month to stay with an average 46% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

FAQs when booking a hotel in Chestertown

  • How do I find a hotel in central Chestertown?

    After you launch a hotel search on KAYAK, you can refine your research by neighbourhood, 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 centre

  • 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

Chestertown Hotel Deals. Search and compare hotels in Chestertown. Find cheap hotel rooms in Chestertown. KAYAK searches hundreds of travel sites to help you find cheap hotels and book the room that suits you best.

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