Chestertown hotels

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Best Chestertown hotels

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R1 235 - R1 827R1 827 - R2 403R2 403 - R2 995R2 995 - R3 570R3 570+ per night

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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(258)
Parking
Free Wi-Fi
Pool
Pet-friendly
R1 557+
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 252+
Check availability
The Lodge at Great Oak Landing - Chestertown - Building
The Lodge at Great Oak Landing
Chestertown, MD, United States
Lodge
R2 132+
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)
House
Free Wi-Fi
Air conditioning
R10 017+
Check availability
Driftwood Inn - Chestertown - Bedroom
Driftwood Inn
Chestertown, MD, United States
4.4Mediocre(163)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R1 168+
Check availability
Breathtaking waterfront home on the Chester River - Chestertown - Dining room
Breathtaking waterfront home on the Chester River
Chestertown, MD, United States
9.9Wonderful(22)
House
Free Wi-Fi
Air conditioning
R14 146+
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(52)
House
Free Wi-Fi
Air conditioning
R5 499+
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(24)
Apartment
Free Wi-Fi
Air conditioning
R7 530+
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)
House
Air conditioning
R24 010+
Check availability
Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities - Chestertown - Living room
Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
Chestertown, MD, United States
9.9Wonderful(64)
House
Free Wi-Fi
Air conditioning
R10 237+
Check availability
Country Estate in Historic District - Chestertown - Bedroom
Country Estate in Historic District
Chestertown, MD, United States
10Wonderful(46)
House
Free Wi-Fi
Air conditioning
R6 294+
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
9.9Wonderful(20)
House
Free Wi-Fi
Air conditioning
R21 743+
Check availability
The Lazy River House - Chestertown - Living room
The Lazy River House
Chestertown, MD, United States
10Wonderful(10)
House
Air conditioning
R10 694+
Check availability
Historic Downtown Garden Oasis with Private Patio - Chestertown - Patio
Historic Downtown Garden Oasis with Private Patio
Chestertown, MD, United States
9.8Wonderful(19)
Apartment
Free Wi-Fi
Air conditioning
R3 841+
Check availability
John L Stam House - Chestertown
John L Stam House
Chestertown, MD, United States
Free Wi-Fi
Air conditioning
R3 570+
Check availability
Brampton 1860 - Chestertown
Brampton 1860
Chestertown, MD, United States
9.7Wonderful(42)
Parking
Free Wi-Fi
Air conditioning
R5 144+
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 564. In comparison, December is the most expensive month, with prices at R4 434.

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 R1 994. The highest prices are found on Friday, with average rates at R5 280.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

January
December
R2 829
R4 455
Cheapest month to stay with an average 43% drop in price.
Most expensive month to stay with an average 60% 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 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

All hotels in Chestertown