Chester Vacation Rentals

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Vacation Rentals in Chester

Dollhouse in Central Historic St Michaels

St Michaels MD

With a stay at this vacation home in St. Michaels (Downtown St. Michaels), you'll be within a 5-minute walk of Muskrat Park and Higgins Yacht Yard and Marina.

Kitchen

Washer

The Blue Crab Beach House - Free beach passes

North Beach MD

When you stay at this vacation home in North Beach, you'll be by the sea, within a 10-minute walk of Chesapeake Bay and Bayside History Museum.

Kitchen

Washer

Private Cottage on gated estate

Annapolis MD

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

Kitchen

Washer

"La Licorne" Waterfront Beach Cottage

North Beach MD

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

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, a 2-minute drive from U.S. Naval Academy and 14 minutes from Chesapeake Bay.

Kitchen

Washer

Waterfront 4 BR home with private pier and boat dock

Grasonville MD

Located in Grasonville, this vacation home is on the waterfront, within a 10-minute drive of Chesapeake Exploration Center and Queenstown Premium Outlets.

Beautiful 3 Bedroom Retreat walking distance to Downtown St. Michaels

Saint Michaels MD

A stay at this vacation home places you in the heart of St. Michaels, within a 10-minute walk of Classic Motor Museum and Windon Distilling.

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

Crownsville MD

$201 nightly

$229 total

Apr 30 - May 1

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.

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, a 3-minute drive from U.S. Naval Academy and 12 minutes from Chesapeake Bay Bridge.

Kitchen

Washer

Spacious Luxe USNA Home - Pool, Hot Tub, Grill

Annapolis MD

With a stay at this vacation home in Annapolis (Murray Hill), you'll be within a 15-minute drive of U.S. Naval Academy and Chesapeake Bay Bridge.

Pool

Hot Tub

Pool & Yard Retreat | 4BR | 20 Min to Annapolis

Harwood MD

This family-friendly vacation home is 12.3 mi (19.8 km) from Chesapeake Bay and 13.4 mi (21.6 km) from U.S. Naval Academy.

Hot Tub

Kitchen

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

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 Harbor.

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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.