Chestertown Cottages

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

Cottages in Chestertown

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Stevensville MD

With a stay at this cottage in Stevensville, you'll be within a 5-minute drive of Romancoke Wharf County Park and Chesapeake Bay.

Kitchen

Washer

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Pasadena MD

$583 nightly

$665 total

Dec 8 - Dec 9

Total with taxes and fees

When you stay at this cottage in Pasadena, you'll be within a 10-minute drive of Chesapeake Bay and Northern Chesapeake Bay.

Kitchen

Washer

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Rosedale MD

$431 nightly

$498 total

Dec 8 - Dec 9

Total with taxes and fees

With a stay at this cottage in Rosedale, you'll be within a 15-minute drive of Baltimore Inner Harbor Marina and Johns Hopkins University.

Kitchen

Washer

Secluded Cozy Cottage in Historic Downtown

Annapolis MD

$627 nightly

$714 total

Jan 3 - Jan 4, 2026

Total with taxes and fees

With a stay at this cottage in Annapolis (Historic District), you'll be within a 15-minute walk of U.S. Naval Academy and 14 Fleet Street.

Kitchen

Washer

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Stevensville MD

$802 nightly

$885 total

Dec 8 - Dec 9

Total with taxes and fees

With a stay at this cottage in Stevensville, you'll be within a 5-minute drive of Romancoke Wharf County Park and Chesapeake Bay.

Kitchen

Washer

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Fall fun!

Annapolis MD

With a stay at this cottage in Annapolis (Cape Saint Claire), you'll be within a 15-minute drive of U.S. Naval Academy and Chesapeake Bay.

Hot Tub

Breakfast included

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

annapolis MD

With a stay at this cottage, you'll be centrally located in Annapolis, within a 15-minute drive of U.S. Naval Academy and Annapolis Bowl.

Hot Tub

Kitchen

Cozy, unique, historic registered cottage on the Corsica River!

Centreville MD

With a stay at this cottage in Centreville, you'll be within a 15-minute drive of Hazel Miner Monument and Earle Landing.

Kitchen

Washer

Rare find! Chic cottage, salt water heated pool May 15-Oct15.

Arnold MD

With a stay at this cottage in Arnold, you'll be within a 15-minute drive of U.S. Naval Academy and Bay Hills Golf Club.

Pool

Kitchen

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville MD

Located in Earleville, this cottage is in a rural location, within a 15-minute drive of Earleville Wildlife Management Area and Earleville Wildlife Management Area.

Kitchen

Washer

Eastern shore beachfront cottage with stunning sunset views!

Worton MD

Located in Worton, this cottage is on the waterfront, within a 10-minute drive of Betterton Community Park and Betterton Historic District.

Kitchen

Washer

Eastern Shore beach cottage get-away

Rock Hall MD

With a stay at this cottage in Rock Hall, you'll be just steps from Ferry Park and Chesapeake Bay.

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.