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$159 per night from 29 Apr to 30 Apr
NZ$159
per night
29 Apr - 30 Apr
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. Discover ...
7.2/10 Good! (257 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 13 Apr. 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 NZ$213 per night from 30 Apr to 1 May
NZ$213
per night
30 Apr - 1 May
Stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.4/10 Very Good! (665 reviews)
"Super nice and friendly front desk staff. The room was very clean and spacious (suite). I’ve had less than positive experiences at other Comfort Inns, but this one is the exception. I’d absolutely stay here again!"

Reviewed on 9 Apr. 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$292 per night from 13 May to 14 May
NZ$292
per night
13 May - 14 May
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 rooms ...
8.8/10 Excellent! (1,604 reviews)
"Lovely historic Inn, excellent help, excellent valet."

Reviewed on 24 Apr. 2024

Historic Inns of Annapolis
See all 997 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
Enjoy WiFi, a fitness center, and onsite parking. Popular attractions Chesapeake Bay Bridge and Sandy Point State Park are located nearby. Discover genuine guest ...
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, onsite parking, and a garden. Our guests praise the clean rooms in our reviews. Popular attractions Elk ...
9.8/10 Exceptional! (35 reviews)
Come for the view, stay for the neighbors
"Nicely redone two BR cottage, lots of space in LR for pull out couch (my son found it was decent quality 👍). Wonderful to have a water view from both the front and back decks - short walk to the water (6 houses back?). Treats on arrival were a kind bonus. Even though it rained a few days, found ..."

Reviewed on 11 Apr. 2024

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!
Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!
Havre De Grace
Stay at this vacation home in Havre De Grace. Enjoy free WiFi, a water park, and onsite parking. Popular attractions Susquehanna Museum at the Lock House and ...
9.6/10 Exceptional! (41 reviews)
Family time together
"The cottage was perfect for my mama and me! Everything worked out really well.The location was great, close to everything. Having the yard was a bonus for my brother and his dog. We loved setting out on the front porch and having breakfast in the back yard. Your cottage is a beautiful place and we ..."

Reviewed on 12 Apr. 2024

Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!
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