Chestertown
Travel Guide

Quaint Chestertown awaits: its sports, university life, history, and more!

Venture to sights like Wilmer Park and Rolphs Wharf Marina as you discover Chestertown—a city also notable for its college vibe.

Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2 out of 5
160 Scheeler Rd, Chestertown, MD
The price is $90 per night from Jun 6 to Jun 6
Located in the heart of Chestertown, this hotel is 0.6 mi (1 km) from Washington College and within 32 mi (52 km) of Queenstown Premium Outlets and Queenstown ...
4/5Very Good! (109 reviews)
"Expedia wouldn’t let me cancel one night so I paid for two nights"

Reviewed on May 3, 2021

Red Roof Inn & Suites Chestertown
Great Oak Manor
Great Oak Manor
3.5 out of 5
10568 Cliff Rd, Chestertown, MD
The price is $199 per night from May 18 to May 18
Nestled on the beach, this Chestertown bed & breakfast is next to a golf course and 9.1 mi (14.6 km) from Washington College.
4.7/5Exceptional! (35 reviews)
"Absolutely gorgeous setting and grounds. Breakfast was yummy and healthy. Lots of alternatives to eat. Gravel road driveway a little difficult to maneuver bags."

Reviewed on Apr 11, 2021

Great Oak Manor
Holiday Inn Express Hotel & Suites Chestertown, an IHG Hotel
Holiday Inn Express Hotel & Suites Chestertown, an IHG Hotel
2.5 out of 5
150 Scheeler Road, Chestertown, MD
The price is $104 per night from May 17 to May 17
Situated in Chestertown, this hotel is 0.6 mi (0.9 km) from Washington College and within 32 mi (52 km) of Queenstown Premium Outlets and Queenstown Harbor Golf ...
4.3/5Excellent! (442 reviews)
"Staf was great!"

Reviewed on May 1, 2021

Holiday Inn Express Hotel & Suites Chestertown, an IHG Hotel
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.
Charming Chestertown Waterfront Cottage
Charming Chestertown Waterfront Cottage
Chestertown, MD
Set in Chestertown, this family-friendly vacation home is 3 mi (4.9 km) from Wilmer Park and 3.6 mi (5.7 km) from Washington College. The Mainstay and Tilmon's ...
4.9/5Exceptional! (14 reviews)
Wonderful Place!!
"We had such a wonderful stay! Michelle was super helpful and the house was well equipped for cooking, relaxing by the fire, playing ping pong and kayaking. It is a short distance to town and walking path. Highly recommend and plan tk return!"

Reviewed on May 13, 2021

Charming Chestertown Waterfront Cottage
Country Estate in Historic District
Country Estate in Historic District
Chestertown, MD
The price is $247 per night from May 19 to May 19
Situated in Chestertown, this vacation home is 0.8 mi (1.3 km) from Washington College and within 25 mi (40 km) of Queenstown Premium Outlets and Queenstown ...
5/5Exceptional! (7 reviews)
This has become a destination...
"Though we, originally, stayed here as we passed through to another destination this home and it’s hosts have turned it into a destination for us. With its proximity to both the city and beach, while remaining uniquely itself, we cannot wait to visits again someday!"

Reviewed on May 6, 2021

Country Estate in Historic District
Waterfront W/deepwater Pier Walking Distance to Downtown Chestertown
Waterfront W/deepwater Pier Walking Distance to Downtown Chestertown
Chestertown, MD
This family-friendly Chestertown vacation home is located on the waterfront, 1.5 mi (2.4 km) from Washington College, and within 25 mi (40 km) of Queenstown ...
5/5Exceptional! (49 reviews)
The perfect weekend getaway
"Love everything about this property!!Came here for a ladies weekend getaway. It was to homes for us, thoughtfully designed, extremely clean, uncluttered, with a million dollar view of the water. We went in February and so the fireplace and fire pit outside were both welcome additions, as was the ..."

Reviewed on Mar 19, 2021

Waterfront W/deepwater Pier Walking Distance to Downtown 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 in Chestertown

Reviews of Chestertown

4.1

Top Destination

5 - Excellent
8
5 - Excellent 26.666666666666668%
4 - Good
17
4 - Good 56.666666666666664%
3 - Okay
5
3 - Okay 16.666666666666668%
2 - Disappointing
0
2 - Disappointing 0%
1 - Terrible
0
1 - Terrible 0%

5/5 - Excellent

Krista

Aug 12, 2019

Chestertown is a beautiful place.

5/5 - Excellent

Verified traveler

Jul 24, 2019

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

Jun 17, 2019

Definitely the Land of Pleasant Living!

3/5 - Okay

jana

Jun 13, 2019

We went to Washington College. Downtown Chestertown was cute.

4/5 - Good

WashDad23

Apr 19, 2019

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

5/5 - Excellent

Verified traveler

Apr 11, 2019

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.