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

Relaxing Waterfront Cottage Near St Michaels, Maryland

With a stay at this cottage in Wittman, you'll be on the waterfront, and 7.7 mi (12.4 km) from Phillips Wharf Environmental Center and 8.1 mi (13.1 km) from Tilghman Watermen’s Museum.

Pool

Kitchen

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

With a stay at this cottage in St. Michaels, you'll be a 5-minute walk from St. Michaels Museum and 7 minutes by foot from St. Michaels Winery.

Kitchen

Washer

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

$948

includes taxes & fees

$859 per night

Dec 15 - Dec 16

When you stay at this cottage in Stevensville, you'll be 9 minutes by car from Matapeake State Park.

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

With a stay at this cottage, you'll be centrally located in Edgewater, within a 15-minute drive of Sand Point Marsh and South River Golf Links.

Kitchen

Washer

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

With a stay at this cottage in St. Michaels, you'll be within a 10-minute walk of St. Michaels Museum and Chesapeake Bay Maritime Museum.

Eastern Shore Waterside Cottage Near St. Michaels

With a stay at this cottage in Neavitt, you'll be on the waterfront, and 9.9 mi (16 km) from Chesapeake Bay Maritime Museum and 10.1 mi (16.2 km) from St. Michaels Museum.

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

With a stay at this cottage in St. Michaels, you'll be within a 10-minute walk of Chesapeake Bay Maritime Museum and St. Michaels Museum.

Kitchen

Washer

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

This cottage is 19.1 mi (30.8 km) from U.S. Naval Academy and 3.3 mi (5.2 km) from Franklin Point State Park.

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

When you stay at this cottage in Tilghman, you'll be 12 minutes by foot from Tilghman Watermen’s Museum.

Waterfront property with private boat ramp and new dock!

When you stay at this cottage in Cambridge, you'll be 8 minutes by car from Spocott Windmill.

Washer

Dryer

North Beach Cottage - Walk to Chesapeake Bay

Located in North Beach, this cottage is by the sea, a 3-minute walk from Bayside History Museum and within a 5-minute drive of Chesapeake Beach Water Park.

Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

When you stay at this cottage in St. Leonard, you'll be by the sea and 15 minutes by car from Perigeaux Vineyards and Winery.

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.