Chestertown Motels

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Motels in Chestertown

Super 8 by Wyndham Baltimore/Essex Area

98 Stemmers Run Rd, I-695 Exit 36 Essex MD

$75 nightly

$87 total

Dec 9 - Dec 10

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

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.

Breakfast included

Parking included

Village Inn Annapolis MD

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.

Pet friendly

Parking included

Days Inn by Wyndham Aberdeen

783 W Bel Air Ave Aberdeen MD

$55 nightly

$62 total

Dec 14 - Dec 15

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

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 Hospital.

Pool

Breakfast included

Super 8 by Wyndham Aberdeen MD

1008 Beards Hill Rd Aberdeen MD

$48 nightly

$53 total

Dec 21 - Dec 22

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

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.

Breakfast included

Pet friendly

Mariners Motel

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.

Pool

Pet friendly

Driftwood Inn

609 Washington Avenue Chestertown MD

$64 nightly

$70 total

Dec 24 - Dec 25

Total with taxes and fees

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.

Pet friendly

Parking included

White Marsh Motel

11131 Pulaski Highway White Marsh MD

$60 nightly

$69 total

Jan 3 - Jan 4, 2026

Total with taxes and fees

Located in White Marsh, White Marsh Motel is a 4-minute drive from Gunpowder Falls State Park and 6 minutes from Johns Hopkins Medicine.

Parking included

Free WiFi

Rodeway Inn

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.

Breakfast included

Parking included

Regal Inn & Suites

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 University.

Parking included

Free WiFi

Bayside Inn & Suites

424 S Philadelphia Blvd Aberdeen MD

Located in Aberdeen, Bayside Inn & Suites is a 1-minute drive from Cal Ripken Museum and 7 minutes from Kirk U.S. Army Health Clinic.

Parking included

Free WiFi

Hillside Motel

2630 Centreville Rd. Centreville MD

Located in Centreville, Hillside Motel is a 1-minute drive from Hazel Miner Monument and 9 minutes from Queenstown Premium Outlets.

Parking included

Free WiFi

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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.