Chester Vacation Rentals

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Vacation Rentals in Chester

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

Crownsville MD

$185 nightly

$210 total

Nov 1 - Nov 2

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

Annapolis MD

$422 nightly

$481 total

Nov 3 - Nov 4

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

Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital

Annapolis MD

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

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

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

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

Cozy 2br home w/ parking in downtown Annapolis

Annapolis MD

$466 nightly

$531 total

Nov 1 - Nov 2

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

Thorneton Point Estate

Easton MD

Located in Easton, this vacation home is on the waterfront, within a 10-minute drive of Saint Michaels Village and St. Michaels Winery.

Pool

Hot Tub

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

Navy Weekend Haven, Family-Friendly Luxury Home w Fenced-in Backyard & Parking

Annapolis MD

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

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.