Chester Guest Houses

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 Chester hotels

Guest Houses in Chester

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Stevensville MD

Located in Stevensville, this guesthouse is on the waterfront, within a 10-minute drive of Paul Reed Smith Guitars and Chesapeake Bay.

Pool

Hot Tub

Riverview Retreat on Warehouse Creek - sleeps 6

Edgewater MD

With a stay at this guesthouse in Edgewater, you'll be on the waterfront, within a 15-minute drive of U.S. Naval Academy and South River Golf Links.

Pet friendly

Air conditioning

West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis

Annapolis MD

$268 nightly

$306 total

Dec 8 - Dec 9

Total with taxes and fees

With a stay at this guesthouse, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and People's Brewer Hill Cemetery.

Free WiFi

Air conditioning

Newly Renovated Guest House located in Oxford MD

Oxford MD

Located in Oxford, this guesthouse is on the waterfront, within a 5-minute drive of Play Ball Dog Park and Oxford Museum.

Free WiFi

Air conditioning

The Shallow Creek Shore Shack on the Chesapeake Bay

Sparrows Point MD

When you stay at this guesthouse in Edgemere, you'll be on the waterfront, within a 5-minute drive of Patapsco River and Chesapeake Bay.

Free WiFi

Air conditioning

Don't see what you're looking for?

See all available properties in Chester

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.