Shady Side 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 Shady Side

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Annapolis MD

$570 nightly

$650 total

Aug 25 - Aug 26

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

NEW KI Creek Retreat! 3BR/2bath water view, private house near KI wedding venues

Stevensville MD

With a stay at this vacation home in Stevensville, you'll be within a 10-minute drive of Chesapeake Bay and Northern Chesapeake Bay.

Washer

Dryer

Cute, Cozy 2-bedroom house near Annapolis with water access

Crownsville MD

$207 nightly

$235 total

Aug 23 - Aug 24

Total with taxes and fees

With a stay at this vacation home in Crownsville (Herald Harbor), you'll be a 4-minute drive from Joyces Marina and 9 minutes from Eisenhower Golf Course.

Kitchen

Washer

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Crofton MD

A stay at this vacation home places you in the heart of Crofton, within a 5-minute drive of Walden Golf Club and Regal Waugh Chapel.

Kitchen

Washer

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

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

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis MD

$464 nightly

$528 total

Aug 23 - Aug 24

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 Annapolis City Dock.

Air conditioning

Laundry

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.

Kitchen

Washer

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, steps from Annapolis City Dock and 4 minutes by foot from U.S. Naval Academy.

Kitchen

Washer

Light and airy cottage minutes to Naval Academy

Severna Park MD

With a stay at this vacation home in Severna Park, you'll be within a 15-minute drive of U.S. Naval Academy and Sandy Point State Park.

Kitchen

Washer

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

Stevensville MD

$324 nightly

$334 total

Aug 26 - Aug 27

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.

Kitchen

Washer

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Annapolis City Dock.

Kitchen

Washer

Recently Renovated Annapolis Home - Conveniently Located

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Annapolis City Dock.

Kitchen

Washer

Don't see what you're looking for?

See all available properties in Shady Side

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.