Chestertown Travel Guide

Tourist Guide
Photo by Assya A
Photo by Assya A
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 ฿2,965 per night from 12 Jun to 13 Jun
฿2,965
per night
12 Jun - 13 Jun
Stay at this hotel in Chestertown. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Popular attraction Rolphs Wharf Marina is located nearby.
7.2/10 Good! (275 reviews)
"We have stayed here many times before and I was able to book a one night stay for our quick trip this time. Very comfortable and relaxing, rooms are nice"

Reviewed on 31 May 2024

Red Roof Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 out of 5
150 Scheeler Road, Chestertown, MD
The price is ฿4,672 per night from 27 Jun to 28 Jun
฿4,672
per night
27 Jun - 28 Jun
Stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
8.4/10 Very Good! (678 reviews)
"Was clean and good for the purpose of the trip"

Reviewed on 1 Jun 2024

Comfort Inn & Suites Chestertown
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
The price is ฿5,007 per night from 1 Jul to 2 Jul
฿5,007
per night
1 Jul - 2 Jul
Stay at this historic hotel in Annapolis. Enjoy free Wi-Fi, room service and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (1,627 reviews)
"We loved our vacation close to home! The staff was accommodating and helpful. :)"

Reviewed on 5 Jun 2024

Historic Inns of Annapolis
See all 994 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.
Majestic Hotel & Apartments
Majestic Hotel & Apartments
3 out of 5
7th St & Boardwalk, Ocean City, MD
Stay at this 3-star beach aparthotel in Ocean City. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
6.4/10 (76 reviews)
"Plumbing needs work but fantastic stay!"

Reviewed on 31 May 2024

Majestic Hotel & Apartments
WhyHotel by Placemakr Columbia
WhyHotel by Placemakr Columbia
4 out of 5
6200 Valencia Ln, Columbia, MD
Stay at this 4-star aparthotel in Columbia. Enjoy free Wi-Fi, a fitness centre and parking (surcharge). Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (394 reviews)
"This property is A1 check it out you won’t be disappointed."

Reviewed on 1 Jun 2024

WhyHotel by Placemakr Columbia
Shore Point Cottages
Shore Point Cottages
3 out of 5
9543 Stephen Decatur Hwy, Berlin, MD
Stay at this 3-star cottage in Berlin. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Ocean City Beach and Ocean City Boardwalk are ...
9.2/10 Wonderful! (65 reviews)
"Check In was quick and convenient! The property was amazing - cute, calm and peaceful. Definitely child friendly! Even my teenagers enjoyed it. Very close to Ocean Beach boardwalk and various restaurants and stores. I will definitely stay here again."

Reviewed on 3 Jun 2024

Shore Point Cottages
See all 14,068 properties in Maryland
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

Image for Washington College

Washington College

Enjoy the student vibe when you visit Washington College during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

Washington College
Image for Rolphs Wharf Marina

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
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River Arts Chestertown

Enjoy the student vibe when you visit River Arts Chestertown during your trip to Chestertown. Take in the festivals in this family-friendly area.

River Arts Chestertown
Image for Garfield Center for the Arts at the Prince Theater

Garfield Center for the Arts at the Prince Theater

You can make plans for a show 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
Image for Historical Society of Kent County Maryland

Historical Society of Kent County Maryland

You can spend an afternoon browsing the exhibits at Historical Society of Kent County Maryland during your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

Historical Society of Kent County Maryland
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Wilmer Park

Explore the great outdoors at Wilmer Park, a lovely green space in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

Wilmer Park