16 Best Hotels in Chestertown, Maryland - KAYAK

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These are the best prices for 19-20 3월.

Comfort Inn and Suites Chestertown - Chestertown - Living room

Comfort Inn and Suites Chestertown

Chestertown, MD, United States

8,0

R1 506+

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Red Roof Inn & Suites Chestertown - Chestertown - Building

Red Roof Inn & Suites Chestertown

Chestertown, MD, United States

6,9

R1 260+

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The Lodge at Great Oak Landing - Chestertown - Building

The Lodge at Great Oak Landing

Chestertown, MD, United States

0,0

R2 717+

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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

10,0

R11 865+

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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

10,0

R7 659+

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Country Estate in Historic District - Chestertown - Bedroom

Country Estate in Historic District

Chestertown, MD, United States

10,0

R6 579+

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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

10,0

R11 865+

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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

10,0

R5 073+

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Harbor View Haven | Waterfront W/ Hot Tub + Dock! - Chestertown - Patio

Harbor View Haven | Waterfront W/ Hot Tub + Dock!

Chestertown, MD, United States

10,0

R9 655+

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Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm! - Chestertown - Living room

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Chestertown, MD, United States

10,0

R4 059+

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Driftwood Inn - Chestertown - Bedroom

Driftwood Inn

Chestertown, MD, United States

4,7

R1 129+

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First Floor Studio Apartment in Historic Chestertown - Chestertown - Bedroom

First Floor Studio Apartment in Historic Chestertown

Chestertown, MD, United States

9,5

R2 766+

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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

9,8

R8 755+

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Newly restored apartment in the heart of Chestertown - Chestertown - Dining room

Newly restored apartment in the heart of Chestertown

Chestertown, MD, United States

9,7

R6 415+

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Breathtaking waterfront home on the Chester River - Chestertown - Dining room

Breathtaking waterfront home on the Chester River

Chestertown, MD, United States

9,9

R14 270+

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Historic Downtown Garden Oasis with Private Patio - Chestertown - Patio

Historic Downtown Garden Oasis with Private Patio

Chestertown, MD, United States

9,9

R3 862+

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Great Oak Manor - Chestertown

Great Oak Manor

Chestertown, MD, United States

9,4

R2 706+

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River Cottage, Chestertown - Chestertown - Living room

River Cottage, Chestertown

Chestertown, MD, United States

9,0

R5 090+

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Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access - Chestertown - Living room

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access

Chestertown, MD, United States

10,0

R6 039+

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Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock. - Chestertown - Patio

Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.

Chestertown, MD, United States

10,0

R6 399+

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Blue Heron Farm Waterfront Chalet - Chestertown - Living room

Blue Heron Farm Waterfront Chalet

Chestertown, MD, United States

10,0

R7 135+

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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

9,9

R7 152+

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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 November, with average rates of R1 543/night. In comparison, October is the most expensive month, with prices at R5 688/night.

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 895/night. The highest prices are found on Friday, with average rates at R4 622/night.

How early should you book a hotel in Chestertown?

Book at least 42 days before your stay begins to get the best price for your Chestertown hotel.

Low season	High season	Average price (weeknight)	Average price (weekend night)
November	October	R2 715	R3 716
Cheapest month to stay with an average 50% drop in price.	Most expensive month to stay with an average 82% rise in price.	Average Sun - Thu price over the last 2 weeks.	Average Fri & Sat price over the last 2 weeks.

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.

All hotels in Chestertown