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Cheap Hotels in Chestertown, MD from $70

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Check availability on Chestertown Cheap Hotels

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Tonight
Jul 11 - Jul 12
Tomorrow
Jul 12 - Jul 13
This weekend
Jul 11 - Jul 13
Next weekend
Jul 18 - Jul 20

Top Chestertown Cheap Hotels

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Recommended hotels in Chestertown

Red Roof Inn & Suites Chestertown
Classic hotel room with a large bed, bedside tables, and a comfortable armchair.

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (372)
"Had a good time and enjoyed the quietness at the hotel. "
$68 nightly
The price is $76
Jul 23 - Jul 24
Total includes taxes and fees
Red Roof Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
Welcome to our reception area, where friendly staff are available to assist with your stay.

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (778)
"Comfortable room, friendly staff. "
$112 nightly
The price is $125
Aug 3 - Aug 4
Total includes taxes and fees
Comfort Inn & Suites Chestertown
The Lodge at Great Oak Landing
Surrounded by a tranquil lake, this serene setting features a cozy fire pit amidst a picturesque landscape.

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very Good, (53)
"not super fancy but really well done. comfy beds and a first rate chef. plus great for the boating crowd"
$147 nightly
The price is $163
Jul 13 - Jul 14
Total includes taxes and fees
The Lodge at Great Oak Landing
First Floor Studio Apartment in Historic Chestertown
Relax by the pool surrounded by a tranquil golf course view.

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (90)
"Very pretty location. Few minutes drive to town center."
$144 nightly
The price is $159
Jul 17 - Jul 18
Total includes taxes and fees
First Floor Studio Apartment in Historic Chestertown
Driftwood Inn
Rows of rooms with stone facades and windows line the building's side.

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"
$64 nightly
The price is $70
Jul 14 - Jul 15
Total includes taxes and fees
Driftwood Inn
Quality Inn
Enjoy a sumptuous spread of fresh bread, pastries, and fruits at our buffet counter.

Quality Inn

2.5 star property
7.6 out of 10, Good, (1001)
"2nd time staying here no major issues "
$100 nightly
The price is $111
Jul 27 - Jul 28
Total includes taxes and fees
Quality Inn
Relax Inn Smyrna
Commercial building with a brick facade and flat roof, featuring an office entrance and a service entrance.

Relax Inn Smyrna

2.0 star property
7.8 out of 10, Good, (81)
"The owner/staff were so sweet and helpful "
$91 nightly
The price is $99
Aug 4 - Aug 5
Total includes taxes and fees
Relax Inn Smyrna
Hampton Inn Middletown
Guests can dine in comfort at this hotel's spacious dining area, surrounded by six chairs and a large window with sheer curtains.

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (814)
"Front desk service was exceptional!!"
$124 nightly
The price is $138
Aug 10 - Aug 11
Total includes taxes and fees
Hampton Inn Middletown
Holiday Inn Express And Suites Middletown by IHG
Relax in our stylish lobby with a seating area, reception desk, and digital display.

Holiday Inn Express And Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (590)
"I would like to share, the staff at the hotel was very pleasant, it felt like a home away from home, and I also enjoyed the breakfast that was offered. "
$115 nightly
The price is $128
Aug 10 - Aug 11
Total includes taxes and fees
Holiday Inn Express And Suites Middletown by IHG
Fairfield Inn & Suites by Marriott Middletown
Relax in this stylish living space with a large flat-screen TV, dining area, and comfortable sofa.

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (251)
"Nice place to stay"
$115 nightly
The price is $128
Aug 10 - Aug 11
Total includes taxes and fees
Fairfield Inn & Suites by Marriott Middletown
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.

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.