An aerial view of a town with a river, buildings, and surrounding greenery.

Find Cheap Hotels in Chestertown, MD

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Check availability on Chestertown Cheap Hotels

Tonight
Sep 1 - Sep 2
Tomorrow
Sep 2 - Sep 3
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

Our top choices for Chestertown cheap hotels

1. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Linda
NT$2,276
NT$2,527 total
includes taxes & fees
Sep 10 - Sep 11
Red Roof Inn & Suites Chestertown

2. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
NT$3,284
NT$3,646 total
includes taxes & fees
Sep 27 - Sep 28
Comfort Inn & Suites Chestertown

3. Driftwood Inn

Driftwood Inn
Chestertown
United States
Vanesa
NT$2,008
NT$2,229 total
includes taxes & fees
Sep 2 - Sep 3
Driftwood Inn

4. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
United States
Lynda
NT$3,415
NT$3,904 total
includes taxes & fees
Sep 2 - Sep 3
The Lodge at Great Oak Landing

5. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
United States
Eileen
NT$3,085
NT$3,456 total
includes taxes & fees
Sep 7 - Sep 8
Home2 Suites by Hilton Baltimore / Aberdeen, MD

6. Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
Havre De Grace
United States
Sharon
NT$1,767
NT$1,979 total
includes taxes & fees
Sep 3 - Sep 4
Super 8 by Wyndham Havre De Grace Aberdeen Area

7. Motel Edgewood

Motel Edgewood
Edgewood
United States
Kamau
NT$1,707
NT$1,912 total
includes taxes & fees
Sep 6 - Sep 7
Motel Edgewood

8. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
United States
Faezeh
NT$3,168
NT$3,516 total
includes taxes & fees
Sep 28 - Sep 29
Quality Inn Grasonville near Kent Island

9. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
United States
walter
NT$2,645
NT$2,962 total
includes taxes & fees
Sep 13 - Sep 14
Hampton Inn & Suites Edgewood/Aberdeen-South

10. Haven Point Inn and Gallery

Haven Point Inn and Gallery
Rock Hall
United States
John
NT$3,970
NT$4,406 total
includes taxes & fees
Sep 2 - Sep 3
Haven Point Inn and Gallery
View all properties

Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"No complaints! Place was clean, felt safe. Staff were great!"
Gary 2-night trip
Posted 1 day ago
Best Western Plus Hotel & Conference Center
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

10/10 Excellent
"The staff is always very welcoming. The staff who cleans are the same. I do know that when I look out the window to the back parking lot...people leave their trash all over the place same with over filling the trash cans on the 2nd floor. The staff tends to these areas all of the time."
Sondra 4-night trip
Posted 4 days ago
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

Frequently asked questions

What is Chestertown like for travelers on a budget?
Chestertown has a variety of cheap accommodations and places to visit, making it a great getaway spot for budget travelers. You can find ways to save money while getting to know this destination, which is home to attractions like Chestertown Historic District, Northern Chesapeake Bay, and Chesapeake Bay.
When is the best time for a budget trip to Chestertown?
Weather will likely play an important role when you plan your trip to Chestertown, and keep in mind that cheaper options are usually available when the weather isn't as good. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What is there to see and do in Chestertown?
You don't have to spend a fortune to find things to see and do in Chestertown. You can budget for the local attractions that interest you most, and then plan some activities that cost little or nothing at all. If you're eager to get outdoors, you can enjoy the natural setting at Northern Chesapeake Bay, Chesapeake Bay, or Chestertown Dog Park.
How can I get to Chestertown and get around on a budget?
Scoping out the transportation options in Chestertown is a smart way to keep your trip affordable. The nearest airport is Baltimore, MD (MTN-Martin State), 20.3 mi (32.7 km) away. However, if that doesn't suit your budget, the next closest is 28.2 mi (45.3 km) away: Easton, MD (ESN-Easton - Newnam). Chestertown might not have very many public transportation choices so a car rental could be an economical alternative to see the area.

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