Chestertown Vacation Rentals

Name: The Posh Residence
Price range: $689 total

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Vacation Rentals in Chestertown

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

Crownsville MD

$175 nightly

$199 total

Nov 15 - Nov 16

Total with taxes and fees

With a stay at this vacation home in Crownsville (Herald Harbor), you'll be within a 15-minute drive of Joyces Marina and Annapolis Bowl.

Kitchen

Washer

Charming 2-bedroom house with fitness room and AC in Glen Burnie

Glen Burnie MD

With a stay at this vacation home in Glen Burnie, you'll be within a 10-minute drive of Baltimore Cruise Terminal and Horseshoe Casino Baltimore.

Kitchen

Washer

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

5BR Chesapeake Waterfront Estate with Private Dock

Perryville MD

With a stay at this vacation home in Perryville, you'll be within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay.

Kitchen

Washer

Welcome to our newly built house

Glen Burnie MD

With a stay at this vacation home in Glen Burnie (Marley), you'll be within a 15-minute drive of Arundel Mills Mall and Maryland Live Casino.

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

Historic Home with Parking Steps From Capital & USNA

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

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville MD

With a stay at this vacation home in Stevensville, you'll be next to a golf course, within a 5-minute drive of Chesapeake Bay and Matapeake State Park.

Pool

Kitchen

Hudson house

3037 Hudson St Baltimore MD

With a stay at this vacation home in Baltimore (Canton), you'll be a 5-minute drive from Johns Hopkins Hospital and 8 minutes from Baltimore Inner Harbor Marina.

Kitchen

Washer

Cozy 2br home w/ parking in downtown Annapolis

Annapolis MD

$372 nightly

$424 total

Nov 30 - Dec 1

Total with taxes and fees

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

Kitchen

Washer

Peaceful Pet-Friendly Stay - Near USNA and Beaches

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, a 4-minute drive from Chesapeake Bay and 13 minutes from Annapolis City Dock.

Kitchen

Washer

The Posh Residence

Glen Burnie MD

$604 nightly

$689 total

Nov 29 - Nov 30

Total with taxes and fees

With a stay at this vacation home in Glen Burnie (Marley), you'll be within a 15-minute drive of Arundel Mills Mall and Maryland Live Casino.

Kitchen

Washer

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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.