5/5 - Excellent
Krista
Chestertown is a beautiful place.
Visit Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
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! (767 reviews)
"The breakfast was consistently tasty."
Reviewed on 31 May 2025
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
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! (361 reviews)
"Was a decent place to stay for the price."
Reviewed on 29 May 2025
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd, Chestertown, MD
The price is SAR 496 per night from Jun 19 to Jun 20
SAR 496
SAR 551 total
19 Jun - 20 Jun
includes taxes & fees
Stay at this 3.5-star beach lodge in Chestertown. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point ...
7.8/10 Good! (50 reviews)
"Absolutely loved our stay here! The staff were so kind and accommodating. The room was very clean and bed was comfortable. Jellee Fish Joel's (the beach bar) just received a huge makeover and we had a blast! we will be back again soon!"
Reviewed on 2 June 2025
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.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Chestertown
Stay at this cabin in Chestertown. Enjoy a garden, laundry facilities, and patios. Popular attractions Chase Island and Crumpton Auction are located nearby.
Beautiful house in an awesome location.
"My family and I had the best time at the Outrange. The house is super cool. But the access to hiking, kayaking and even goats made it perfect. Ben is super good at communication. He responded to any of my questions quickly. I can't say enough about it. Just a really lovely property."
Reviewed on 12 May 2025
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Annapolis
Book a stay at this family-friendly vacation home in Annapolis. Enjoy free WiFi, a water park, and laundry facilities. Popular attractions John Smith House and ...
10/10 Exceptional! (200 reviews)
Spring Break in Annapolis
"We decided to take the full fam to Annapolis for the kids’ spring break and we had a blast at this proprety"
Reviewed on 18 May 2025
BAYSIDE BUNGALOW
Rock Hall
Stay at this vacation home in Rock Hall. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Ferry Park and Waterman’s Museum are located ...
10/10 Exceptional! (38 reviews)
Charming
"Enjoyed sitting on the porch and just relaxing. This cottage is very charming and peaceful. Would highly recommend."
Reviewed on 18 May 2025
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
4/5(13 reviews)
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.
Rolphs Wharf Marina
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
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.
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.
River Arts Chestertown
Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.
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.
Reviews of Chestertown
4.1
Top Destination
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.
- Washington College
- Rolphs Wharf Marina
- Historical Society of Kent County Maryland
- Wilmer Park
- River Arts Chestertown
- Garfield Center for the Arts at the Prince Theater
- Crumpton Auction
- Baltimore Cruise Terminal
- U.S. Naval Academy
- Annapolis City Dock
- Chesapeake Bay Bridge
- Sandy Point State Park
- Ripken Stadium
- Navy-Marine Corps Memorial Stadium
- Susquehanna River
- White Marsh Mall
- Cedar Lane Regional Park
- Rock Hall Harbor
- Harford Community College
- Sandy Point Beach
- Fort McHenry
- Havre de Grace Promenade
- Cal Ripken Museum
- Bohemia Vista Marina