5/5 - Excellent
Krista
Aug 12, 2019Chestertown is a beautiful place.
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is ￥11,916 per night from May 28 to May 29
￥11,916
per night
May 28 - May 29
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attraction Rolphs Wharf Marina is located nearby.
7.2/10 Good! (262 reviews)
"This is a conveniently located and comfortable Inn/Hotel. It was perfect for a one night stay. The only deficit was the lack of a simple, continental breakfast room necessitating a walk to the local DD/Dunkin'."
Reviewed on Apr 13, 2024
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
The price is ￥19,123 per night from May 16 to May 17
￥19,123
per night
May 16 - May 17
Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (669 reviews)
"Everything was great"
Reviewed on May 5, 2024
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is ￥26,574 per night from May 28 to May 29
￥26,574
per night
May 28 - May 29
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,612 reviews)
"The location was excellent, the room wss very nice bit was decorated in a fashion that was too modern give the name of the hotel. The staff was friendly and efficient but said they would send an Anniversary present to our room but it never arrived. The facility was good but the elevator was too ..."
Reviewed on May 9, 2024
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.
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 concierge services. Popular attractions Sandy Point State Park and Bay Hills Golf ...
10/10 Exceptional! (2 reviews)
Amazing
"My rugby team traveled down for a competition. Erin met us there walked us around the property and gave us great recommendations for food in the area. She was an amazing manager, always answering questions and getting us anything we needed. The property was beautiful and fit our entire team comfortably. ..."
Reviewed on Apr 23, 2024
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Earleville
Stay at this cottage in Earleville. Enjoy free WiFi, a garden, and patios. Our guests praise the clean rooms in our reviews. Popular attractions Elk Neck State ...
9.6/10 Exceptional! (36 reviews)
Modern convenience plus quiet and a good rest.
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in ..."
Reviewed on May 2, 2024
The Heron's Nest at Atlantic Marina
Pasadena
Stay at this cottage in Pasadena. Enjoy free WiFi, a garden, and an in-room coffeemaker. Our guests praise the clean rooms in our reviews. Popular attractions ...
9.8/10 Exceptional! (263 reviews)
Beautiful place on the water
"Fun little getaway, love the setting at the local neighborhood, don’t miss Irv’s basement bar…"
Reviewed on May 10, 2024
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.
River Arts Chestertown
Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.
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.
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.
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.
Reviews of Chestertown
4.1
Top Destination
5/5 - Excellent
Verified traveler
Jul 24, 2019None 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, 2019Definitely the Land of Pleasant Living!
3/5 - Okay
jana
Jun 13, 2019We went to Washington College. Downtown Chestertown was cute.
4/5 - Good
WashDad23
Apr 19, 2019Small attractive college town on the bay, good restaurants, nice period houses
5/5 - Excellent
Verified traveler
Apr 11, 2019We 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.