Chester Vacation Rentals

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Vacation Rentals in Chester

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

Crownsville MD

$213 nightly

$242 total

Aug 3 - Aug 4

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.

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.

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.

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.

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.

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.

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

Annapolis MD

$611 nightly

$697 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.

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

Stevensville MD

$314 nightly

$340 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.

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.

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Tilghman Island MD

When you stay at this vacation home in Tilghman, you'll be on the waterfront, within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay.

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis MD

$533 nightly

$608 total

Aug 5 - Aug 6

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.

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.

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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.