Chestertown hotels

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Best Chestertown hotels

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2+ stars3+ stars

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6+ Okay7+ Good8+ Great9+ Excellent

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R1 309 - R1 903R1 903 - R2 496R2 496 - R3 089R3 089 - R3 683R3 683+ per night

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Free cancellationFree breakfastFree parkingFree internet

Most recommended Chestertown hotels

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Comfort Inn and Suites Chestertown - Chestertown - Living room
Comfort Inn and Suites Chestertown
Chestertown, MD, United States
8.0Very Good(255)
Parking
Free Wi-Fi
Pool
Pet-friendly
R1 571+
Check availability
Red Roof Inn & Suites Chestertown - Chestertown - Living room
Red Roof Inn & Suites Chestertown
Chestertown, MD, United States
6.9Okay(35)
Air conditioning
R1 449+
Check availability
The Lodge at Great Oak Landing - Chestertown - Building
The Lodge at Great Oak Landing
Chestertown, MD, United States
R2 688+
Check availability
Driftwood Inn - Chestertown - Bedroom
Driftwood Inn
Chestertown, MD, United States
4.5Mediocre(163)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R1 204+
Check availability
First Floor Studio Apartment in Historic Chestertown - Chestertown - Bedroom
First Floor Studio Apartment in Historic Chestertown
Chestertown, MD, United States
9.5Wonderful(79)
Free Wi-Fi
Air conditioning
R2 775+
Check availability
Private Waterfront Paradise W/ Pier - Kayak To Historic Chestertown! - Chestertown - Living room
Private Waterfront Paradise W/ Pier - Kayak To Historic Chestertown!
Chestertown, MD, United States
9.8Wonderful(56)
Free Wi-Fi
Air conditioning
R9 268+
Check availability
Pet-Friendly Home on Chester River with Dock! - Chestertown - Living room
Pet-Friendly Home on Chester River with Dock!
Chestertown, MD, United States
9.6Wonderful(5)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
R15 360+
Check availability
Circa 1900 Home in the Heart of Historic Downtown Chestertown - Chestertown - Living room
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Chestertown, MD, United States
10Wonderful(51)
Free Wi-Fi
Air conditioning
R7 837+
Check availability
Carriage House Hideaway In Center of Chestertown - Chestertown - Bedroom
Carriage House Hideaway In Center of Chestertown
Chestertown, MD, United States
9.9Wonderful(69)
Free Wi-Fi
Pet-friendly
Air conditioning
R3 369+
Check availability
Country Estate in Historic District - Chestertown - Bedroom
Country Estate in Historic District
Chestertown, MD, United States
10Wonderful(46)
Free Wi-Fi
Air conditioning
R8 814+
Check availability
Breathtaking waterfront home on the Chester River - Chestertown - Dining room
Breathtaking waterfront home on the Chester River
Chestertown, MD, United States
9.8Wonderful(19)
Free Wi-Fi
Air conditioning
R15 953+
Check availability
Newly restored apartment in the heart of Chestertown - Chestertown - Dining room
Newly restored apartment in the heart of Chestertown
Chestertown, MD, United States
9.7Wonderful(23)
Free Wi-Fi
Air conditioning
R8 448+
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
9.9Wonderful(41)
Air conditioning
R10 857+
Check availability
Beautiful, Spacious Waterfront Home, An Easy Walk To Historic Chestertown - Chestertown - Living room
Beautiful, Spacious Waterfront Home, An Easy Walk To Historic Chestertown
Chestertown, MD, United States
9.5Wonderful(13)
Air conditioning
R28 538+
Check availability
John L Stam House - Chestertown
John L Stam House
Chestertown, MD, United States
Free Wi-Fi
Air conditioning
R3 683+
Check availability
Brampton 1860 - Chestertown
Brampton 1860
Chestertown, MD, United States
9.7Wonderful(42)
Parking
Free Wi-Fi
Air conditioning
R6 039+
Check availability

Popular filters in Chestertown hotels

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Booking Insights

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 R1 613. In comparison, December is the most expensive month, with prices at R4 574.

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

Sunday offers the lowest rates in Chestertown, with an average nightly price of R2 057. The highest prices are found on Friday, with average rates at R5 446.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

January
December
R2 939
R4 596
Cheapest month to stay with an average 44% drop in price.
Most expensive month to stay with an average 58% 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

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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