Chestertown hotels

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Best Chestertown hotels

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R0 - R951R951 - R1 901R1 901 - R2 852R2 852 - R3 784R3 784+ per night

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Free cancellationFree breakfastFree parkingFree internet

Most recommended Chestertown hotels

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Red Roof Inn & Suites Chestertown - Chestertown - Bedroom
Red Roof Inn & Suites Chestertown
Chestertown, MD, United States
6.9Okay(35)
Free Wi-Fi
Pet-friendly
Air conditioning
R1 830+
Check availability
Comfort Inn and Suites Chestertown - Chestertown - Living room
Comfort Inn and Suites Chestertown
Chestertown, MD, United States
8.0Very Good(236)
Parking
Free Wi-Fi
Pool
Pet-friendly
R2 497+
Check availability
Great Oak Manor - Chestertown
Great Oak Manor
Chestertown, MD, United States
9.3Wonderful(63)
Free Wi-Fi
Air conditioning
R2 965+
Check availability
Inn At Mitchell House - Chestertown
Inn At Mitchell House
Chestertown, MD, United States
Free Wi-Fi
R2 977+
Check availability
First Floor Studio Apartment in Historic Chestertown - Chestertown - Bedroom
First Floor Studio Apartment in Historic Chestertown
Chestertown, MD, United States
Free Wi-Fi
Air conditioning
R3 390+
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John L Stam House - Chestertown
John L Stam House
Chestertown, MD, United States
Free Wi-Fi
Air conditioning
R3 784+
Check availability
The Lodge at Great Oak Landing - Chestertown - Building
The Lodge at Great Oak Landing
Chestertown, MD, United States
R4 914+
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Cottage within walking distance to the Bay! - Chestertown - Living room
Cottage within walking distance to the Bay!
Chestertown, MD, United States
Air conditioning
R5 901+
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Historic downtown Chestertown Home. #1 Location. - Chestertown
Historic downtown Chestertown Home. #1 Location.
Chestertown, MD, United States
Free Wi-Fi
Air conditioning
R6 744+
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, United States
Free Wi-Fi
Pet-friendly
Air conditioning
R10 098+
Check 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
Air conditioning
R10 582+
Check availability
Chester River Waterfront, Magnificent Views, Dock, Beach, Close 2 Town - Chestertown - Living room
Chester River Waterfront, Magnificent Views, Dock, Beach, Close 2 Town
Chestertown, MD, United States
Free Wi-Fi
Pet-friendly
Air conditioning
R12 483+
Check availability
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown - Chestertown - Restaurant
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
Chestertown, MD, United States
Air conditioning
R12 860+
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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
Air conditioning
R16 071+
Check 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
Air conditioning
R22 258+
Check availability
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
Air conditioning
R24 357+
Check availability

Popular filters 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 R29 728. In comparison, September is the most expensive month, with prices at R79 802.

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 R39 318. The highest prices are found on Thursday, with average rates at R99 825.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

January
September
R2 853
R3 931
Cheapest month to stay with an average 46% drop in price.
Most expensive month to stay with an average 62% 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

All hotels in Chestertown

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