Chestertown Packages (Flight + Hotel)

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Top hotels in 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 ฿3,305 per night from 30 Nov to 1 Dec
฿3,305
฿3,669 total
30 Nov - 1 Dec
includes taxes & fees
8.4/10 Very Good! (848 reviews)
Good location. Very pricey but not much competition

Reviewed on 17 Nov 2025

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 ฿2,333 per night from 30 Nov to 1 Dec
฿2,333
฿2,590 total
30 Nov - 1 Dec
includes taxes & fees
7.2/10 Good! (417 reviews)
room was clean but the shower curtain was in tatters. multiple rings torn off

Reviewed on 20 Nov 2025

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 ฿3,208 per night from 25 Nov to 26 Nov
฿3,208
฿3,668 total
25 Nov - 26 Nov
includes taxes & fees
7.8/10 Good! (76 reviews)
Beautiful view

Reviewed on 8 Nov 2025

The Lodge at Great Oak Landing
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.