Chestertown

Travel Guide
Photo by Assya A
Photo by Assya A
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2 out of 5
160 Scheeler Rd, Chestertown, MD
The price is €84 per night from 23 Jun to 24 Jun
€84
per night
23 Jun - 24 Jun
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! (279 reviews)
"We have stayed here many times before and I was able to book a one night stay for our quick trip this time. Very comfortable and relaxing, rooms are nice"

Reviewed on 31 May 2024

Red Roof Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 out of 5
150 Scheeler Road, Chestertown, MD
The price is €132 per night from 18 Jun to 19 Jun
€132
per night
18 Jun - 19 Jun
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

Comfort Inn & Suites Chestertown
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is €146 per night from 30 Jun to 1 Jul
€146
per night
30 Jun - 1 Jul
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! (1,622 reviews)
"It was our first stay in Annapolis. We were very impressed with the condition of the hotel."

Reviewed on 13 Jun 2024

Historic Inns of Annapolis
See all 988 properties in Chestertown
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
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! (35 reviews)
Wonderful spot
"My family of 4 stayed here. So many things to do outside-truly a good time. So many games and accessories to have an easy good time. Would definitely stay at this place again."

Reviewed on 28 May 2024

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
See all properties in Chestertown
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

Image for Washington College

Washington College

Enjoy the student vibe when you visit Washington College during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

Washington College
Image for Rolphs Wharf Marina

Rolphs Wharf Marina

Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.

Rolphs Wharf Marina
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River Arts Chestertown

Enjoy the student vibe when you visit River Arts Chestertown during your trip to Chestertown. Take in the festivals in this family-friendly area.

River Arts Chestertown
Image for Garfield Center for the Arts at the Prince Theater

Garfield Center for the Arts at the Prince Theater

You can make plans for a show 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.

Garfield Center for the Arts at the Prince Theater
Image for Historical Society of Kent County Maryland

Historical Society of Kent County Maryland

You can spend an afternoon browsing the exhibits at Historical Society of Kent County Maryland during your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

Historical Society of Kent County Maryland
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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.

Wilmer Park