Odyssey Vacation Rentals

Name: Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Price range: $365 total

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Vacation Rentals in Odyssey

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.

The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach MD

Located in Owings, this vacation home is within a 5-minute drive of Bayside History Museum and Chesapeake Bay.

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

Annapolis MD

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.

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.

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Prince Frederick MD

$372 nightly

$394 total

Dec 9 - Dec 10

Total with taxes and fees

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

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

$603 nightly

$650 total

Jan 5 - Jan 6, 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.

Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

Annapolis MD

With a stay at this vacation home in Annapolis (Cape St. John), you'll be within a 15-minute drive of U.S. Naval Academy and Annapolis Harbour Center.

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Port Republic MD

When you a stay at this vacation home in Port Republic, you'll be on the beach, just steps from Chesapeake Bay and Northern Chesapeake Bay.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Prince Frederick MD

$344 nightly

$365 total

Dec 17 - Dec 18

Total with taxes and fees

Located in Prince Frederick, this vacation home is near the beach, within a 5-minute walk 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.