5/5 - Excellent
Krista
Aug 12, 2019Chestertown is a beautiful place.
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La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct, Rosedale, MD
The price is $86 per night from Jun 11 to Jun 12
$86
per night
Jun 11 - Jun 12
Stay at this business-friendly hotel in Rosedale. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
7.2/10 Good! (1,000 reviews)
"Clean and friendly staff."
Reviewed on Jun 1, 2023
Best Western Plus Hotel & Conference Center
5625 O'Donnell Street, Baltimore, MD
The price is $102 per night from Jun 18 to Jun 19
$102
per night
Jun 18 - Jun 19
Stay at this hotel in Baltimore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular ...
7.4/10 Good! (1,000 reviews)
"Very good"
Reviewed on May 30, 2023
Hampton Inn Baltimore Bayview Campus
6571 Eastern Avenue, Baltimore, MD
The price is $116 per night from Jul 9 to Jul 10
$116
per night
Jul 9 - Jul 10
Stay at this business-friendly hotel in Baltimore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
9/10 Wonderful! (855 reviews)
Reviewed on Jun 4, 2023
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.
Carriage House Hideaway in Middle of Chestertown
Chestertown
Stay at this family-friendly apartment in Chestertown. Enjoy free WiFi, onsite parking, and a garden. Discover genuine guest reviews for Carriage House Hideaway ...
10/10 Exceptional! (51 reviews)
"Fantastic location, gorgeous space, and great host!"
Reviewed on May 26, 2023
Hidden gem with water and golf course views! Bike ride to downtown!
Chestertown
Stay at this golf vacation home in Chestertown. Enjoy free WiFi, onsite parking, and a garden. Discover genuine guest reviews for Hidden gem with water and golf ...
10/10 Exceptional! (14 reviews)
Beautiful Home
"Home was fantastic. Beautiful inside and out. Would definitely stay again if it’s available next time we come to town."
Reviewed on Mar 28, 2023
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Chestertown
Stay at this family-friendly vacation home in Chestertown. Enjoy free WiFi, onsite parking, and a garden. Our guests praise the comfy beds in our reviews. Discover ...
9.8/10 Exceptional! (47 reviews)
Memorial weekend stay
"Comfortable, well equipped rental home. Enjoyed all the amenities, with the dock and deck and lovely views of the river. Enjoyed sunrise one morning and watching the river come to life with the birds, and early morning scullers rowing. Had a cookout one night and lit a fire in the fire pit. So ..."
Reviewed on Jun 1, 2023
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.
River Arts Chestertown
Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.
Rolphs Wharf Marina
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. 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.
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.
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
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.
- Washington College Vacations
- River Arts Chestertown Vacations
- Rolphs Wharf Marina Vacations
- Wilmer Park Vacations
- Historical Society of Kent County Maryland Vacations
- Garfield Center for the Arts at the Prince Theater Vacations
- U.S. Naval Academy Vacations
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- Ripken Stadium Vacations
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- Rock Hall Harbor Vacations
- Susquehanna River Vacations
- Queenstown Harbor Golf Club Vacations
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Additional information about Expedia Group
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