Chestertown hotels
KAYAK searches hundreds of travel sites at once for hotels in Chestertown, Maryland
...and more
Here is why travellers choose KAYAK
Free to useThere are no hidden charges or fees
Filter your dealsFilter by free cancellation, free breakfast and more.
Millions of reviewsCheck ratings based on millions of real guest reviews.
Best Chestertown hotels
Discover the best hotels in Chestertown and compare prices, ratings, and locations to find the right stay for your trip.
These are the best prices for 10-11 Oct.
First Floor Studio Apartment in Historic Chestertown
Chestertown, MD, United States
Free Wi-Fi
Pool
Air conditioning
Newly restored apartment in the heart of Chestertown
Chestertown, MD, United States
Free Wi-Fi
Air conditioning
Private Waterfront Paradise W/ Pier - Kayak To Historic Chestertown!
Chestertown, MD, United States
Air conditioning
Cheap hotels in Chestertown
These are the cheapest hotels for 10-11 Oct.
3 Mi to Washington College! Updated Home w/ Patio
Chestertown, MD, United States
Parking
Free Wi-Fi
Air conditioning
The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown
Chestertown, MD, United States
Air conditioning
Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.
Chestertown, MD, United States
Pool
Air conditioning
Hotel deals for the weekend
Some of KAYAK users' favourite hotels available 10-11 Oct.
Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River
Chestertown, MD, United States
Air conditioning
Historic Manor House on Beautiful Eastern Shore Estate
Chestertown, MD, United States
Pool
Air conditioning
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
Chestertown, MD, United States
Air conditioning
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Chestertown, MD, United States
Air conditioning
Top-rated hotels
Stay at the hotels that our users loved the most 10-11 Oct.
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Chestertown, MD, United States
Free Wi-Fi
Air conditioning
Chester River Waterfront, Magnificent Views, Dock, Beach, Close 2 Town
Chestertown, MD, United States
Free Wi-Fi
Air conditioning
Lovely Home in Chestertown - Free EV Charging for guests
Chestertown, MD, United States
Free Wi-Fi
Air conditioning
Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
Chestertown, MD, United States
Free Wi-Fi
Air conditioning
Popular filters in Chestertown hotels
Hotels with parking
Comfort Inn and Suites Chestertown and others
Hotels with free cancellation
Explore hotel deals with free cancellation in the area
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 July, with average rates of R1 446/night. In comparison, December is the most expensive month, with prices at R4 346/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 427/night. The highest prices are found on Saturday, with average rates at R3 900/night.
How early should you book a accommodation in Chestertown?
Book at least 20 days before your stay begins to get the best price for your Chestertown accommodation.
Good to know
Low season | High season | Average price (weeknight) | Average price (weekend night) |
|---|---|---|---|
July | December | R2 378 | R3 397 |
Cheapest month to stay with an average 47% 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. |