Hot Rates on Cheap Chestertown Motels

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Featured Motels in Chestertown

Super 8 by Wyndham Baltimore/Essex Area

Super 8 by Wyndham Baltimore/Essex Area

2 out of 5
98 Stemmers Run Rd, I-695 Exit 36 Essex MD
Fully refundableReserve now, pay when you stay
The price is AU$121 per night from 5 Jan to 6 Jan
AU$121
5 Jan - 6 Jan 2026
includes taxes & fees
With a stay at Super 8 by Wyndham Baltimore/Essex Area in Essex, you'll be within a 15-minute drive of Johns Hopkins Hospital and Essex Marina.
Opens in a new windowSuper 8 by Wyndham Baltimore/Essex Area
Village Inn Annapolis MD

Village Inn Annapolis MD

2 out of 5
69 Old Mill Bottom Rd Annapolis MD
With a stay at Village Inn Annapolis MD in Annapolis, you'll be within a 10-minute drive of U.S. Naval Academy and Maryland World War II Memorial.
Opens in a new windowVillage Inn Annapolis MD
Days Inn by Wyndham Aberdeen

Days Inn by Wyndham Aberdeen

2 out of 5
783 W Bel Air Ave Aberdeen MD
Fully refundableReserve now, pay when you stay
The price is AU$103 per night from 25 Jan to 26 Jan
AU$103
25 Jan - 26 Jan 2026
includes taxes & fees
Located in Aberdeen, Days Inn by Wyndham Aberdeen is in the business district, a 4-minute drive from Ripken Stadium and 10 minutes from Harford Memorial ...
Opens in a new windowDays Inn by Wyndham Aberdeen
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Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD

2 out of 5
1008 Beards Hill Rd Aberdeen MD
Fully refundableReserve now, pay when you stay
The price is AU$85 per night from 25 Jan to 26 Jan
AU$85
25 Jan - 26 Jan 2026
includes taxes & fees
Located in Aberdeen, Super 8 by Wyndham Aberdeen MD is in a shopping district, within a 5-minute drive of Cal Ripken Museum and Ripken Stadium.
Opens in a new windowSuper 8 by Wyndham Aberdeen MD
Mariners Motel

Mariners Motel

2 out of 5
5681 South Hawthorne Avenue Rock Hall MD
Located in Rock Hall, Mariners Motel is near the bay, a 3-minute walk from Rock Hall Harbor and 13 minutes by foot from Ferry Park.
Opens in a new windowMariners Motel
Driftwood Inn

Driftwood Inn

2 out of 5
609 Washington Avenue Chestertown MD
With a stay at Driftwood Inn in Chestertown, you'll be a 3-minute walk from Washington College and 12 minutes by foot from Rolling Road Park.
Opens in a new windowDriftwood Inn
White Marsh Motel

White Marsh Motel

2 out of 5
11131 Pulaski Highway White Marsh MD
Fully refundableReserve now, pay when you stay
Located in White Marsh, White Marsh Motel is a 4-minute drive from Gunpowder Falls State Park and 6 minutes from Johns Hopkins Medicine.
Opens in a new windowWhite Marsh Motel
Rodeway Inn

Rodeway Inn

2.5 out of 5
74 Old Mill Bottom Rd N Annapolis MD
With a stay at Rodeway Inn, you'll be centrally located in Annapolis, within a 10-minute drive of U.S. Naval Academy and Maryland World War II Memorial.
Opens in a new windowRodeway Inn
Regal Inn & Suites

Regal Inn & Suites

2 out of 5
8005 Pulaski Hwy Rosedale MD
With a stay at Regal Inn & Suites in Rosedale, you'll be within a 15-minute drive of Baltimore Inner Harbor Marina and Johns Hopkins Hospital.
Opens in a new windowRegal Inn & Suites
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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.

Chestertown Motel Accommodation

You live your life freestyle, always ready for the next adventure. You practically invented the phrase “YOLO”, and your most used hashtag is #travelgram. Or maybe it’s #wanderlust. The world can’t box you in with hashtags, that’s for sure! When you travel, that last thing on your mind is where you’re going to sleep—but you’ve come to the right place. At lastminute.com.au, not only do we get you, we also have plenty of motel rooms in Chestertown.

We bet one of these scenarios sounds familiar: You’re on your way back from an amazing overseas adventure or important conference, but your connecting flight is delayed, and you need a place to crash. Or maybe you were on the most epic of road trips, but you got distracted by all the sights and now you’ve gotta get some rest, stat. But just because you’re low maintenance doesn’t mean you don’t want a great deal. Chestertown motels have everything you need at the price you want, like parking, Wi-Fi, and maybe even a pool—not that you’ll be there long enough to even really need it. There are adventures to be had!

Listen, we get it. Motels come in handy in so many situations, they might as well be called “those shoes that go with everything”. And the time has come that you need a motel in Chestertown, and you need it ASAP. We’re not here to judge. We’re just here to save the day with our great selection of cheap motels in Chestertown.

Chestertown Motels essential information

Accommodation
11 Motels
Lowest Price
AU$85
Highest Price
AU$643
Popular accommodation
Super 8 by Wyndham Baltimore/Essex Area, Village Inn Annapolis MD , Days Inn by Wyndham Aberdeen, Super 8 by Wyndham Aberdeen MD, Mariners Motel, Driftwood Inn, White Marsh Motel, Rodeway Inn, Regal Inn & Suites

Top trending hotels in Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
Fully refundableReserve now, pay when you stay
The price is AU$167 per night from 25 Jan to 26 Jan
AU$167
25 Jan - 26 Jan 2026
includes taxes & fees
When you stay at Comfort Inn & Suites Chestertown in Chestertown, you'll be in the historical district, within a 5-minute drive of Washington College and Historical ...
Opens in a new windowComfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
The price is AU$119 per night from 1 Jan to 2 Jan
AU$119
1 Jan - 2 Jan 2026
includes taxes & fees
A stay at Red Roof Inn & Suites Chestertown places you in the heart of Chestertown, within a 5-minute drive of Washington College and Chestertown Dog Park.
Opens in a new windowRed Roof Inn & Suites Chestertown
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
With a stay at Historic Inns of Annapolis, you'll be centrally located in Annapolis, steps from The Colonial Players and Thurgood Marshall Memorial.
Opens in a new windowHistoric Inns of Annapolis
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Pendry Baltimore

Pendry Baltimore

5 out of 5
1715 Thames St. Baltimore MD
Fully refundableReserve now, pay when you stay
The price is AU$643 per night from 22 Jan to 23 Jan
AU$643
22 Jan - 23 Jan 2026
includes taxes & fees
With a stay at Pendry Baltimore in Baltimore (Fells Point), you'll be within a 5-minute drive of Johns Hopkins Hospital and National Aquarium in Baltimore.
Opens in a new windowPendry Baltimore
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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.

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^Subject to availability and chosen travel dates.