Travel & Transportation in CHESTERTOWN, MD

Great Oak Manor

Hotels

by Great Oak Manor

in Chestertown, MD

August 20, 2026

3 Br Private Vacation Home Vacation Rental In Chestertown, Maryland

Vacation Rentals

by Vrbo

in Chestertown, MD

July 20, 2026

Driftwood Inn

Hotels

by Hotels.com

in Chestertown, MD

July 20, 2026

3 Br Private Vacation Home Vacation Rental In Chestertown, Maryland

Vacation Rentals

by Vrbo

in Chestertown, MD

July 20, 2026

3 Br Private Vacation Home Vacation Rental In Chestertown, Maryland

Vacation Rentals

by Vrbo

in Chestertown, MD

July 20, 2026

4 Br Private Vacation Home Vacation Rental In Chestertown, Maryland

Vacation Rentals

by Vrbo

in Chestertown, MD

July 20, 2026

6 Br Private Vacation Home Vacation Rental In Chestertown, Maryland

Vacation Rentals

by Vrbo

in Chestertown, MD

July 20, 2026

Walk to Historic Chestertown: Dog-friendly Retreat

Hotels

by Hotels.com

in Chestertown, MD

July 20, 2026

6 Br Private Vacation Home Vacation Rental In Chestertown, Maryland

Vacation Rentals

by Vrbo

in Chestertown, MD

July 20, 2026

4 Br Private Vacation Home Vacation Rental In Chestertown, Maryland

Vacation Rentals

by Vrbo

in Chestertown, MD

July 20, 2026

2 Br Private Vacation Home Vacation Rental In Chestertown, Maryland

Vacation Rentals

by Vrbo

in Chestertown, MD

July 20, 2026

3 Br Private Vacation Home Vacation Rental In Chestertown, Maryland

Vacation Rentals

by Vrbo

in Chestertown, MD

July 20, 2026

3 Br Private Vacation Home Vacation Rental In Chestertown, Maryland

Vacation Rentals

by Vrbo

in Chestertown, MD

July 20, 2026

Red Roof Inn & Suites Chestertown

Hotels

by Hotels.com

in Chestertown, MD

July 20, 2026

4 Br Private Vacation Home Vacation Rental In Chestertown, Maryland

Vacation Rentals

by Vrbo

in Chestertown, MD

July 20, 2026

3 Br Private Vacation Home Vacation Rental In Chestertown, Maryland

Vacation Rentals

by Vrbo

in Chestertown, MD

July 20, 2026

4 Br Private Vacation Home Vacation Rental In Chestertown, Maryland

Vacation Rentals

by Vrbo

in Chestertown, MD

July 20, 2026

2 Br Apartment Vacation Rental In Chestertown, Maryland

Vacation Rentals

by Vrbo

in Chestertown, MD

July 20, 2026

1 Br Apartment Vacation Rental In Chestertown, Maryland

Vacation Rentals

by Vrbo

in Chestertown, MD

July 20, 2026

3 Mi to Washington College! Updated Home w/ Patio

Hotels

by Hotels.com

in Chestertown, MD

July 20, 2026

3 Br Private Vacation Home Vacation Rental In Chestertown, Maryland

Vacation Rentals

by Vrbo

in Chestertown, MD

July 20, 2026

3 Br Private Vacation Home Vacation Rental In Chestertown, Maryland

Vacation Rentals

by Vrbo

in Chestertown, MD

July 20, 2026

4 Br Private Vacation Home Vacation Rental In Chestertown, Maryland

Vacation Rentals

by Vrbo

in Chestertown, MD

July 20, 2026

2 Br Private Vacation Home Vacation Rental In Chestertown, Maryland

Vacation Rentals

by Vrbo

in Chestertown, MD

July 20, 2026

4 Br Private Vacation Home Vacation Rental In Chestertown, Maryland

Vacation Rentals

by Vrbo

in Chestertown, MD

July 20, 2026