Chestertown Apartments

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Check dates for Chestertown hotels

Apartments in Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown MD

$144 nightly

$159 total

Dec 8 - Dec 9

Total with taxes and fees

When you stay at this apartment in Chestertown, you'll be next to a golf course, within a 5-minute drive of Wilmer Park and River Arts Chestertown.

Pool

Hot Tub

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall MD

$257 nightly

$284 total

Dec 6 - Dec 7

Total with taxes and fees

With a stay at this apartment in Rock Hall, you'll be a 3-minute walk from The Mainstay and 7 minutes by foot from Rock Hall Harbor.

Kitchen

Washer

Bay View Studio Apartment

Annapolis MD

When you stay at this apartment in Annapolis, you'll be on the waterfront, within a 10-minute walk of Annapolis Sailing School and Annapolis Landing Marina.

Hot Tub

Kitchen

Stunning 2-Bedroom loft apartment in waterfront community near BWI

Glen Burnie MD

With a stay at this apartment in Glen Burnie (Point Pleasant), you'll be within a 15-minute drive of Bingo World and National Electronics Museum.

Pet friendly

Air conditioning

Pristine Downtown 1-Bedroom Steps from State House

Annapolis MD

A stay at this apartment places you in the heart of Annapolis, within a 10-minute walk of U.S. Naval Academy and 97, 99 and 101 East Street.

Kitchen

Washer

Charming Downtown 3rd Floor 1 Bedroom Apt

Annapolis MD

With a stay at this apartment in Annapolis (Historic District), you'll be within a 10-minute walk of U.S. Naval Academy and John Smith House.

Kitchen

Washer

Newly restored apartment in the heart of Chestertown

Chestertown MD

With a stay at this apartment in Chestertown, you'll be just steps from Chestertown Historic District and Garfield Center for the Arts at the Prince Theater.

Kitchen

Washer

Trendy Baltimore Townhome: 2 Mi to Downtown!

Baltimore MD

With a stay at this apartment in Baltimore (Patterson Park), you'll be a 3-minute drive from Johns Hopkins Hospital and 8 minutes from Baltimore Inner Harbor Marina.

Kitchen

Washer

Waterfront Retreat with Private Dock and Beach

Worton MD

$285 nightly

$315 total

Dec 7 - Dec 8

Total with taxes and fees

Located in Worton, this apartment is on the waterfront, within a 15-minute drive of Kinnairds Point Drive and Betterton Community Park.

Kitchen

Free WiFi

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

Baltimore MD

$195 nightly

$225 total

Dec 8 - Dec 9

Total with taxes and fees

With a stay at this apartment in Baltimore (Greektown), you'll be within a 10-minute drive of Baltimore Inner Harbor Marina and Johns Hopkins Hospital.

Washer

Dryer

Waterfront Oasis of Annapolis Star

Annapolis MD

$363 nightly

$414 total

Dec 6 - Dec 7

Total with taxes and fees

With a stay at this apartment, you'll be centrally located in Annapolis, within a 10-minute drive of U.S. Naval Academy and Maryland World War II Memorial.

Pool

Kitchen

Luxury Pool Loft sleeps 4

Annapolis MD

With a stay at this apartment in Annapolis (Cape Saint Claire), you'll be within a 15-minute drive of U.S. Naval Academy and Sandy Point State Park.

Pool

Kitchen

Don't see what you're looking for?

See all available properties in Chestertown

View all properties

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.