5/5 - Excellent
Krista
Chestertown is a beautiful place.
Visit Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
The price is AED 426 per night from Jul 16 to Jul 17
AED 426
AED 473 total
16 Jul - 17 Jul
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! (772 reviews)
"Great hotel in a great community…. Easily accessible to anything nearby."
Reviewed on 15 June 2025
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
The price is AED 231 per night from Jun 25 to Jun 26
AED 231
AED 257 total
25 Jun - 26 Jun
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! (367 reviews)
"Great chain. The only issue is floors are not very clean. If you can't steam-wash carpets often best not to have them. Bathroom floor is sticky. But room is large and comfortable, staff very pleasant."
Reviewed on 16 June 2025
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd, Chestertown, MD
The price is AED 486 per night from Jun 22 to Jun 23
AED 486
AED 539 total
22 Jun - 23 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! (51 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
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Pasadena
Stay at this apartment in Pasadena. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Fort Smallwood Park and Compass Pointe ...
9.6/10 Exceptional! (52 reviews)
10/10 Excellent
"I definitely loved this place, everything was very clean, just like in the photos, I would definitely go back.I really liked the sunset on the lake in the mornings"
Reviewed on 15 June 2025
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Annapolis
Stay at this vacation home in Annapolis. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Annapolis City Dock and Sandy Point State ...
10/10 Exceptional! (27 reviews)
USNA Graduation
"We had 14 family members join us to celebrate my son’s graduation from the Naval Academy. The house is clean, the rooms were great, the property was beautiful, and it was close to USNA. Our family loved the open concept."
Reviewed on 24 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
- Sandy Point State Park
- Ripken Stadium
- Chesapeake Bay Bridge
- 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
- Bohemia Vista Marina
- CopperPlex