5/5 - Excellent
Krista
Aug 12, 2019Chestertown is a beautiful place.
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
The price is SAR89 per night from Jun 26 to Jun 27
SAR89
per night
Jun 26 - Jun 27
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! (280 reviews)
"Not exceptional, but clean."
Reviewed on 16 Jun, 2024
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
The price is SAR141 per night from Jun 24 to Jun 25
SAR141
per night
Jun 24 - Jun 25
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! (680 reviews)
"It was great"
Reviewed on 3 Jun, 2024
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
The price is SAR158 per night from Jul 3 to Jul 4
SAR158
per night
Jul 3 - Jul 4
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! (1,610 reviews)
"Lovely hotel"
Reviewed on 19 Jun, 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.
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Chestertown
Stay at this vacation home in Chestertown. Enjoy free WiFi, private pools, and a garden. Popular attractions Garfield Center for the Arts at the Prince Theater ...
9.8/10 Exceptional! (36 reviews)
Relaxing retreat
"Good location. House well stocked. Great pool. Short hike to river. Lots of kayaks ,a canoe and paddle boards"
Reviewed on 12 Jun, 2024
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 Chesapeake ...
10/10 Exceptional! (5 reviews)
KB's Getaway
"The property was beautiful. The property manager was available for any inquiries we had. My family and I enjoyed it immensely. The view of the water was wonderful whether sitting on the dock or sitting in the sunroom. We played indoor and outdoor games. Perfect place for family bonding. The weather ..."
Reviewed on 3 Jun, 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 2 May, 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.
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
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.
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.