Chestertown, MD

Travel Guide

Photo by Assya A
Photo by Assya A
Photo by Patricia Knorr
Photo by Patricia Knorr
Photo by Patricia Knorr
Photo by Patricia Knorr
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
The price is SAR 389 per night from Dec 29 to Dec 30
SAR 389
SAR 432 total
29 Dec - 30 Dec
includes taxes & fees
Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (860 reviews)
Very nice

Reviewed on 14 December 2025

Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd Chestertown MD
The price is SAR 270 per night from Dec 30 to Dec 31
SAR 270
SAR 300 total
30 Dec - 31 Dec
includes taxes & fees
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
7.2/10 Good! (421 reviews)
Very clean. Pets allowed.

Reviewed on 14 December 2025

Red Roof Inn & Suites Chestertown
Pendry Baltimore

Pendry Baltimore

5 out of 5
1715 Thames St. Baltimore MD
The price is SAR 1,185 per night from Jan 22 to Jan 23
SAR 1,185
SAR 1,547 total
22 Jan - 23 January 2026
includes taxes & fees
Book a stay at this luxury hotel in Baltimore. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (1,000 reviews)
Really nice cozy room we had the terrace balcony would definitely stay again!

Reviewed on 9 December 2025

Pendry Baltimore
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.
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown MD
Book a stay at this golf apartment in Chestertown. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Wilmer Park and Sumner Hall are ...
9.6/10 Exceptional! (108 reviews)
Every thing was great

Reviewed on 7 December 2025

First Floor Studio Apartment in Historic Chestertown
Hudson house

Hudson house

3.5 out of 5
3037 Hudson St Baltimore MD
Stay at this residence in Baltimore. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Baltimore Inner Harbor Marina and Baltimore Cruise ...
Hudson house
Charming 2-bedroom house with fitness room and AC in Glen Burnie

Charming 2-bedroom house with fitness room and AC in Glen Burnie

2 out of 5
Glen Burnie MD
Stay at this vacation home in Glen Burnie. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Baltimore Inner Harbor Marina and Baltimore ...
10/10 Exceptional! (2 reviews)
Very nice and clean and comfortable for my family thank you for hosting

Reviewed on 9 December 2025

Charming 2-bedroom house with fitness room and AC in Glen Burnie
See all 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.

Popular places to visit

Washington College

Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

Washington College

River Arts Chestertown

Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.

River Arts Chestertown

Historical Society of Kent County Maryland

You can spend an afternoon exploring the galleries in Historical Society of Kent County Maryland during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

Historical Society of Kent County Maryland

Rolphs Wharf Marina

Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.

Rolphs Wharf Marina

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

Crumpton Auction

Take the family on an outing to Crumpton Auction during your trip to Chestertown. Take in the festivals while you're in the area.

Crumpton Auction

Reviews of Chestertown

4.1
Top Destination
5 - Excellent
8
5 - Excellent 27%
4 - Good
17
4 - Good 57%
3 - Okay
5
3 - Okay 17%
2 - Disappointing
0
2 - Disappointing 0%
1 - Terrible
0
1 - Terrible 0%

5/5 - Excellent

Krista

Chestertown is a beautiful place.

5/5 - Excellent

Verified traveler

None of the choices Expedia gave me for places I went to were anywhere near Chestertown. Chestertown is a very nice community with wonderful Colonial Houses, a nice harbour, interesting history, and an amazing number of great restaurants.

4/5 - Good

Verified traveler

Definitely the Land of Pleasant Living!

3/5 - Okay

jana

We went to Washington College. Downtown Chestertown was cute.

4/5 - Good

WashDad23

Small attractive college town on the bay, good restaurants, nice period houses

5/5 - Excellent

Verified traveler

We were in Chestertown to visit Washington College. The town is so special and lovely! I would really love to visit when the weather is warmer to enjoy the water and all the offerings in the area.