Odyssey Vacation Rentals
Get more for your budget and save up to 50% off select Secret Bargain hotels
Get even more value with CheapTickets Price Guarantee!
Change your flight without a fee on select flights
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
The price is $394 total per night
$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
The price is $650 total per night
$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
The price is $365 total per night
$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.
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.
Odyssey Vacation Rentals essential information
Accommodation | 518 Vacation Rentals |
|---|---|
Lowest Price | $365 |
Highest Price | $650 |
Popular accommodation | Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA, The Cozy Crab- Your Charming Haven in Lovely North Beach!, Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!, 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!, Charming garden row home, easy 4 block walk to the heart of Annapolis., Location is perfect and a big bonus we have our own parking at the home!, 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!, Gather, Relax & Explore — Townhome 1 Block from State Capitol Building with Backyard & Parking, Edgewater/Mayo Gateaway w/ Hot Tub, Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis, Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier, Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space. |
