Chestertown Vacations

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Find the Best Chestertown Vacation Packages

Chestertown Hotel Deals

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$3,183 per night from Nov 25 to Nov 26
NT$3,183
NT$3,533 total
Nov 25 - Nov 26
includes taxes & fees
8.4/10 Very Good! (848 reviews)
Good location. Very pricey but not much competition

Reviewed on 2025/11/17

Comfort Inn & Suites Chestertown
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$2,247 per night from Nov 30 to Dec 1
NT$2,247
NT$2,494 total
Nov 30 - Dec 1
includes taxes & fees
7.2/10 Good! (414 reviews)
This property was clean but dated. The carpet was stained, the furniture and fixtures were worn and broken, towels were washed but old and in need of replacement.

Reviewed on 2025/11/9

Red Roof 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 refundable
The price is NT$3,089 per night from Nov 25 to Nov 26
NT$3,089
NT$3,532 total
Nov 25 - Nov 26
includes taxes & fees
7.8/10 Good! (75 reviews)
Beautiful view

Reviewed on 2025/11/8

The Lodge at Great Oak Landing
See all 1,084 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.