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

Chestertown Cheap Hotels

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Our top choices for Chestertown cheap hotels

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (462 reviews)
"Perfect for an overnight trip, staff was very helpful."
United States
Anasmel
The price is HK$564
HK$626 total
includes taxes & fees
27 Jul - 28 Jul
Red Roof Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (934 reviews)
"Room excellent, very clean, well stocked breakfast, nice outdoor pool with lots of privacy, great restaurants walking distance"
United States
Davis
The price is HK$893
HK$991 total
includes taxes & fees
3 Aug - 4 Aug
Comfort Inn & Suites Chestertown

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
Chestertown
8.0 out of 10, Very good, (91 reviews)
"Peaceful and beautiful location. Such a relaxing spot. Very clean throughout the whole property. Staff very pleasant and attentive. Would stay here again "
United States
Nicola
The price is HK$1,037
HK$1,186 total
includes taxes & fees
19 Jul - 20 Jul
The Lodge at Great Oak Landing

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (177 reviews)
"Terrible !!! Dirty not clean the owner was rude and didn’t care about the conditions of the room. I asked for partial refund and was denied. Rat poop in the heaters. Dog hair in tubs dead bugs. Body fluids everywhere! Also drug dealers outside with guns. The owner still didn’t care what they were doing. Don’t go to this place it should be shut down !"
United States
Gabriel
The price is HK$498
HK$553 total
includes taxes & fees
16 Jul - 17 Jul
Driftwood Inn

Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
2.0 star property
Havre De Grace
6.6 out of 10, (1,003 reviews)
"The room was very decent and clean. The staff was very helpful. There was little housekeeper service during my 4 day stay"
United States
Anthony
The price is HK$429
HK$481 total
includes taxes & fees
21 Jul - 22 Jul
Super 8 by Wyndham Havre De Grace Aberdeen Area

Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (510 reviews)
"Always clean staff friendly professional used to pretty much live here years ago always worked with me treated me right.Highly recommend 👌 👍"
United States
Stephen
The price is HK$651
HK$742 total
includes taxes & fees
16 Jul - 17 Jul
Village Inn Annapolis MD

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (937 reviews)
"Room was clean and staff took very good care of us"
United States
Carol
The price is HK$829
HK$920 total
includes taxes & fees
4 Aug - 5 Aug
Quality Inn Grasonville near Kent Island

Motel Edgewood

Motel Edgewood
2.0 star property
Edgewood
7.2 out of 10, Good, (17 reviews)
"Bed was clean and crisply made. Occupants were respectful of sleeping hours. Check-in and check-out were simple. Parking was convenient and had easy access to the highway."
United States
Nancy
The price is HK$423
HK$474 total
includes taxes & fees
16 Jul - 17 Jul
Motel Edgewood

Relax Inn Smyrna Dover Coastal Gateway

Relax Inn Smyrna Dover Coastal Gateway
2.0 star property
Smyrna
7.8 out of 10, Good, (105 reviews)
"Stuff"
United States
matt
The price is HK$698
HK$893 total
includes taxes & fees
4 Aug - 5 Aug
Relax Inn Smyrna Dover Coastal Gateway

Red Roof Inn Aberdeen

Red Roof Inn Aberdeen
2.0 star property
Aberdeen
6.4 out of 10, (1,001 reviews)
"Ordinarily you probably wouldn't think to highly of a Red Roof. However, it was surprisingly clean and well maintained. The bed was extremely comfortable. I'd stay here again."
United States
Adam
The price is HK$431
HK$483 total
includes taxes & fees
16 Jul - 17 Jul
Red Roof Inn Aberdeen
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

Frequently asked questions

What is Chestertown like for travellers on a budget?
Chestertown has cheap accommodation options and a range of things to see and do, making it a great holiday choice for budget-conscious travellers. You can find ways to save money while getting to know this destination, which is home to attractions such as Chestertown Historic District, Rolphs Wharf Marina and Northern 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, but bear 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 temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
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 fill your itinerary with 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?
Looking at these ways to get around Chestertown is a smart way to keep your trip affordable. The nearest airport is 20.3 mi (32.7 km) away from the centre in Baltimore, MD (MTN-Martin State). If that doesn't suit your budget, you can book a flight to Easton, MD (ESN-Easton - Newnam), located 28.2 mi (45.3 km) away. Chestertown may not have many public transport options to choose from so a car rental could be a reasonable alternative to explore more of the area.

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