Chestertown Vacation Rentals

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Vacation Rentals in Chestertown

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

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

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

Crownsville MD

$204 nightly

$232 total

Aug 17 - Aug 18

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

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

Stevensville MD

$296 nightly

$320 total

Aug 11 - Aug 12

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

Sophisticated Charmer with Parking & Views of the USNA Chapel Dome

Annapolis MD

A stay at this vacation home places you in the heart of Annapolis, within a 10-minute walk of Annapolis City Dock and U.S. Naval Academy.

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

* NEWLY RENOVATED** Escape to a Beautiful Getaway on the Chesapeake Bay

Perryville MD

With a stay at this vacation home in Perryville, you'll be on the waterfront, within a 5-minute drive of Chesapeake Bay and Chestnut Point Estates and Marina.

Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer

Baltimore MD

$213 nightly

$246 total

Sep 1 - Sep 2

Total with taxes and fees

With a stay at this vacation home in Baltimore (Berea), you'll be a 4-minute drive from Johns Hopkins Hospital and 8 minutes from National Aquarium in Baltimore.

Parkside Comfort & Spaciousness-Family Friendly

Baltimore MD

With a stay at this vacation home in Baltimore (Patterson Park), you'll be within a 5-minute drive of National Aquarium in Baltimore and Johns Hopkins Hospital.

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, just a 4-minute walk from Annapolis City Dock and 8 minutes by foot from U.S. Naval Academy.

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

Stay in the landmark Lighthouse!

Rock Hall MD

With a stay at this vacation home in Rock Hall, you'll be within a 10-minute walk of Chesapeake Bay and Ferry Park.

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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.