St. Michaels Vacation Rentals

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

Vacation Rentals in St. Michaels

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Shady Side MD

With a stay at this vacation home in Shady Side, you'll be within a 10-minute drive of Chesapeake Bay and Shadyside Park.

Kitchen

Washer

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, a 1-minute drive from U.S. Naval Academy and 14 minutes from Chesapeake Bay.

Kitchen

Washer

Charming Annapolis WaterVIEW Home

Annapolis MD

$485 nightly

$553 total

Jun 10 - Jun 11

Total with taxes and fees

With a stay at this vacation home in Annapolis (Arundel on the Bay), you'll be within a 15-minute drive of Chesapeake Bay and Annapolis City Dock.

Hot Tub

Kitchen

PERFECT LOCATION in the heart of history

Annapolis MD

A stay at this vacation home places you in the heart of Annapolis, steps from U.S. Naval Academy and Annapolis City Dock.

Kitchen

Washer

Grace Cottage, St Michaels Walk to everything!

Saint Michaels MD

A stay at this vacation home places you in the heart of St. Michaels, steps from Muskrat Park and Saint Marys Square.

Washer

Dryer

Charming Historic Annapolis Home With Two Off-street Parking Places!

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, a 2-minute drive from U.S. Naval Academy and 14 minutes from Chesapeake Bay.

Kitchen

Washer

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville MD

$296 nightly

$327 total

Jun 15 - Jun 16

Total with taxes and fees

With a stay at this vacation home in Stevensville, you'll be steps from Chesapeake Bay and Northern Chesapeake Bay.

Waterfront Sunset Bayview: sleeps 6

Chester MD

With a stay at this vacation home in Chester, you'll be on the waterfront, within a 15-minute drive of Chesapeake Bay and Chesapeake Exploration Center.

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Cambridge MD

With a stay at this vacation home in Cambridge, you'll be on the waterfront, within a 15-minute drive of Chesapeake Bay and Spocott Windmill.

Kitchen

Washer

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis MD

$531 nightly

$606 total

Jun 22 - Jun 23

Total with taxes and fees

With a stay at this vacation home in Annapolis, you'll be within a 10-minute drive of U.S. Naval Academy and People's Brewer Hill Cemetery.

Cozy 2br home w/ parking in downtown Annapolis

Annapolis MD

$395 nightly

$450 total

Jun 10 - Jun 11

Total with taxes and fees

A stay at this vacation home places you in the heart of Annapolis, within a 15-minute walk of U.S. Naval Academy and Spa Creek.

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, a 2-minute drive from U.S. Naval Academy and 15 minutes from Chesapeake Bay.

Don't see what you're looking for?

See all available properties in St. Michaels

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.