Chester Vacation Rentals

Name: Edgewater/Mayo Gateaway w/ Hot Tub
Price range: $712 total

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Vacation Rentals in Chester

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Annapolis MD

A stay at this vacation home places you in the heart of Annapolis, within a 10-minute walk of U.S. Naval Academy and Ellen O. Moyer Nature Park at Back Creek.

Large 2 bedroom house with private parking in a nice neighborhood

Arnold MD

$287 nightly

$327 total

Dec 8 - Dec 9

Total with taxes and fees

With a stay at this vacation home in Arnold, you'll be within a 15-minute drive of U.S. Naval Academy and Severna Park Golf Center.

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Annapolis MD

$1,047 nightly

$1,194 total

Dec 9 - Dec 10

Total with taxes and fees

This vacation home is in the heart of Annapolis, within a 10-minute walk of Maynard-Burgess House and U.S. Naval Academy.

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.

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Annapolis MD

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

Kitchen

Washer

Location is perfect and a big bonus we have our own parking at the home!

Annapolis MD

With a stay at this vacation home in Annapolis (Historic District), you'll be within a 10-minute walk of U.S. Naval Academy and 97, 99 and 101 East Street.

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Pasadena MD

Located in Pasadena, this vacation home is on the waterfront, within a 10-minute drive of Fort Smallwood Park and Compass Pointe Golf Courses.

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

St. Michaels MD

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

200 steps to the beach!

Rock Hall MD

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

Waterfront Estate w Private Pier, Game Room & Bar

Centreville MD

Located in Centreville, this vacation home is on a river, within a 10-minute drive of Hazel Miner Monument and Earle Landing.

Gather, Relax & Explore — Townhome 1 Block from State Capitol Building with Backyard & 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 Civil Rights Plaque.

Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater MD

$657 nightly

$712 total

Jan 7 - Jan 8, 2026

Total with taxes and fees

With a stay at this vacation home in Edgewater, you'll be within a 10-minute drive of Chesapeake Bay and Northern Chesapeake Bay.

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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.