Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Cheap Hotels & Resorts in Chestertown from AU$87

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Cheap Hotels

Our top choices for Chestertown cheap hotels

Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (921 reviews)
"Great visit"
United States
Danielle
The price is AU$169
includes taxes & fees
9 July - 10 July
Comfort Inn & Suites Chestertown
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (455 reviews)
"Nothing special but good for the price. "
United States
Andreas
The price is AU$113
includes taxes & fees
23 June - 24 June
Red Roof Inn & Suites Chestertown
Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
Chestertown
7.8 out of 10, Good, (87 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 AU$215
includes taxes & fees
15 June - 16 June
The Lodge at Great Oak Landing
Front of property – evening/night

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 AU$100
includes taxes & fees
14 June - 15 June
Driftwood Inn
Basic Single Room

Relax Inn Smyrna Dover Coastal Gateway

Relax Inn Smyrna Dover Coastal Gateway
2.0 star property
Smyrna
7.8 out of 10, Good, (101 reviews)
"Clean room | Friendly Staff | Good heat"
United States
Joe
The price is AU$139
includes taxes & fees
14 June - 15 June
Relax Inn Smyrna Dover Coastal Gateway
Desk, laptop workspace, iron/ironing board, free WiFi

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,010 reviews)
"Great place for an overnight stay"
United States
Chrystal
The price is AU$142
includes taxes & fees
21 June - 22 June
Quality Inn Smyrna
Indoor pool

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (905 reviews)
"I definitely will be booking my stay again in middle town."
United States
Taylor
The price is AU$192
includes taxes & fees
2 July - 3 July
Hampton Inn Middletown
Exterior

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (684 reviews)
"Great location and nice place to stay. Walk to nearby things to do and enjoy. "
United States
Sharon
The price is AU$186
includes taxes & fees
21 June - 22 June
Holiday Inn Express & Suites Middletown by IHG
Property amenity

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (403 reviews)
"Great place to stay"
United States
Angelique
The price is AU$164
includes taxes & fees
21 June - 22 June
Fairfield Inn & Suites by Marriott Middletown
Standard Room, 2 Queen Beds

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, (1,000 reviews)
"Clean. Quiet, and nice breakfast"
United States
Mark
The price is AU$87
includes taxes & fees
15 June - 16 June
Super 8 by Wyndham Havre De Grace Aberdeen Area
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.
View all properties

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

6/10 Okay
"There weren't any amenities. Please note, future guests: the hotel's check-in is located three blocks away from where you will stay."
Evelyn 1-night trip
Posted 3 hours ago
Historic Inns of Annapolis

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.