Chestertown Vacations

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Photo by Patricia Knorr

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Find the Best Chestertown Vacation Packages

Chestertown Hotel Deals

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is NT$2,460 per night from Oct 12 to Oct 13
NT$2,460
NT$2,731 total
Oct 12 - Oct 13
includes taxes & fees
7.2/10 Good! (398 reviews)
"Room temperature was good. Room was also very spacious and clean."

Reviewed on 2025/9/27

Red Roof Inn & Suites Chestertown
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is NT$3,475 per night from Nov 3 to Nov 4
NT$3,475
NT$3,857 total
Nov 3 - Nov 4
includes taxes & fees
8.4/10 Very Good! (825 reviews)
"Nice hotel"

Reviewed on 2025/9/29

Comfort Inn & Suites Chestertown
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 out of 5
22170 Great Oak Landing Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is NT$4,019 per night from Oct 7 to Oct 8
NT$4,019
NT$4,595 total
Oct 7 - Oct 8
includes taxes & fees
7.8/10 Good! (70 reviews)
"Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!"

Reviewed on 2025/9/5

The Lodge at Great Oak Landing
See all 1,081 properties in Chestertown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Chestertown

Wilmer Park

Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.

Wilmer Park

Garfield Center for the Arts at the Prince Theater

You can get tickets for a performance at Garfield Center for the Arts at the Prince Theater on your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

Garfield Center for the Arts at the Prince Theater
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.