Photo by Assya A

Budget Hotels in Chestertown, Maryland

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Budget Hotels

Tonight
Jul 21 - Jul 22
Tomorrow
Jul 22 - Jul 23
This weekend
Jul 25 - Jul 27
Next weekend
Aug 1 - Aug 3

Top Chestertown Budget Hotels

Red Roof Inn & Suites Chestertown
1 bedroom, desk, laptop workspace, blackout drapes

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (379)
"Good location."
The price is P4,375
P4,856 total
includes taxes & fees
Aug 4 - Aug 5
Red Roof Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (785)
"It was a clean comfortable spot to rest for the night. "
The price is P6,546
P7,266 total
includes taxes & fees
Aug 17 - Aug 18
Comfort Inn & Suites Chestertown
Driftwood Inn
Front of property - evening/night

Driftwood Inn

2.0 star property
5.2 out of 10, (171)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is P3,632
P4,032 total
includes taxes & fees
Jul 26 - Jul 27
Driftwood Inn
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.

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"The Inn was the perfect location for a visit to Annapolis-right in the heart of the downtown! Friendly staff and nice accommodations! I will definitely stay there again when I return to Annapolis. "
Mary 1-night trip
Posted 2 days ago
Historic Inns of Annapolis

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 Historical Society of Kent County Maryland, Rolphs Wharf Marina, and Garfield Center for the Arts at the Prince Theater.
What's the best accommodation for a budget-friendly stay in Chestertown?
Based on reviews, Red Roof Inn & Suites Chestertown is a popular 2-star hotel for our travelers looking for an economical choice, and features free WiFi and free parking. Another top option for your budget-friendly stay is Driftwood Inn.
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 Chestertown Dog Park, Urieville Park, or Urieville Lake Fish Management Area.
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.