Chestertown Travel Guide

Tourist Guide

Photo by Assya A
Photo by Assya A
Photo by Patricia Knorr
Photo by Patricia Knorr
Photo by Patricia Knorr
Photo by Patricia Knorr
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road, Chestertown, MD
The price is NZ$209 per night from 7 Sept to 8 Sept
NZ$209
7 Sept - 8 Sept
includes taxes & fees
Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (797 reviews)
"FEELS LIKE PEACEFULLY 👍 👌"

Reviewed on 14 Aug. 2025

Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is NZ$136 per night from 31 Aug to 1 Sept
NZ$136
31 Aug - 1 Sept
includes taxes & fees
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
7.2/10 Good! (387 reviews)
"Great service"

Reviewed on 1 Aug. 2025

Red Roof Inn & Suites Chestertown
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 out of 5
22170 Great Oak Landing Rd, Chestertown, MD
The price is NZ$252 per night from 24 Aug to 25 Aug
NZ$252
24 Aug - 25 Aug
includes taxes & fees
Stay at this 3.5-star beach lodge in Chestertown. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point ...
7.8/10 Good! (65 reviews)
"Perfect place to unwind. Great views of the harbor and marina. You get access to a private beach and there is a cute area for kids to play. The private beach provides chairs and umbrellas. The lodge also has a bar/food on site."

Reviewed on 16 Aug. 2025

The Lodge at Great Oak Landing
See all 1,075 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.
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
Book a stay at this golf apartment in Chestertown. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Wilmer Park and Sumner Hall are ...
9.6/10 Exceptional! (97 reviews)
"Beautiful, spacious, and clean!"

Reviewed on 17 Aug. 2025

First Floor Studio Apartment in Historic Chestertown
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Chestertown
Book a stay at this family-friendly vacation home in Chestertown. Enjoy free breakfast, free WiFi, and laundry facilities. Popular attractions Rolling Road Park ...
9.8/10 Exceptional! (59 reviews)
"Everything we needed was there. Owners next sore are super nice and hrphful."

Reviewed on 25 Jul. 2025

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
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 laundry facilities. Popular attractions Sandy Point State Park and Bay Hills Golf ...
10/10 Exceptional! (31 reviews)
"We had a great time overall! Pickleball courts and pool were the absolute highlights of the trip, with everyone getting in on the fun. The house was gorgeous with the sunroom being a bit hit every morning! Thanks!"

Reviewed on 20 Jul. 2025

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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

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

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

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

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

Wilmer Park

Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.

Wilmer Park

Chestertown Dog Park

Chestertown Dog Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene.

Chestertown Dog Park