Chesapeake Beach 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 Chesapeake Beach hotels

Cottages in Chesapeake Beach

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

North Beach MD

$261 nightly

$277 total

Dec 6 - Dec 7

Total with taxes and fees

With a stay at this cottage in North Beach, you'll be within a 10-minute walk of Bayside History Museum and Chesapeake Bay.

Washer

Dryer

Relaxing Waterfront Cottage Near St Michaels, Maryland

Wittman MD

Located in Wittman, this cottage is on the waterfront, within a 15-minute drive of Wittman Park and CL Open Field.

Pool

Kitchen

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St Michaels MD

With a stay at this cottage in St. Michaels, you'll be just steps from Muskrat Park and St. Michaels Marina.

Pool

Kitchen

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

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels MD

With a stay at this cottage in St. Michaels, you'll be just steps from Muskrat Park and St. Michaels Marina.

Pool

Kitchen

The Middle Point Cabin in Saint Michaels

Neavitt MD

When you stay at this cottage in Neavitt, you'll be steps from Neavitt Park.

Kitchen

Washer

Charming Waterfront Cottage Retreat near St. Michaels

Bozman MD

When you stay at this cottage in Bozman, you'll be 14 minutes by car from Neavitt Park.

Kitchen

Washer

Family and Pet-Friendly, Waterfront with Pier

Cambridge MD

With a stay at this cottage in Cambridge, you'll be on the waterfront, and 5.6 mi (9 km) from Chesapeake Bay and 5.6 mi (9 km) from Northern Chesapeake Bay.

Pool

Kitchen

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cambridge MD

Located in Cambridge, this cottage is on the waterfront, within a 15-minute drive of Spocott Windmill and Chesapeake Bay.

Kitchen

Washer

The Yellow Cottage on Harness Creek

Annapolis MD

With a stay at this cottage in Annapolis (Hillsmere), you'll be within a 15-minute drive of U.S. Naval Academy and Maryland Quiet Waters Park.

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

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Churchton MD

Located in Churchton, this cottage is on the waterfront, within a 10-minute drive of Chesapeake Bay and Northern Chesapeake Bay.

Hot Tub

Kitchen

Don't see what you're looking for?

See all available properties in Chesapeake Beach

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.