Chestertown Travel Guide

Tourist 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 NZ$141 per night from 21 May to 22 May
NZ$141
per night
21 May - 22 May
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! (264 reviews)
"Hotel was a hotel… hated the small toilets… if you go to wipe your hand will end up touching the water.. yuck! If you’re a man and have to poop…. hold your junk up!!!"

Reviewed on 13 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
Fully refundableReserve now, pay when you stay
The price is NZ$234 per night from 20 May to 21 May
NZ$234
per night
20 May - 21 May
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! (671 reviews)
"The onsite manager was very helpful. The staff was very nice."

Reviewed on 13 May 2024

Comfort Inn & Suites Chestertown
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
The price is NZ$322 per night from 28 May to 29 May
NZ$322
per night
28 May - 29 May
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 9 May 2024

Historic Inns of Annapolis
See all 1,021 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.
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 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 23 Apr. 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
The Heron's Nest at Atlantic Marina
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 10 May 2024

The Heron's Nest at Atlantic Marina
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
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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
Image for River Arts Chestertown

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 Wilmer Park

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
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
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