Annapolis

Browse Our Annapolis Vacation Rentals Below

Introducing our newest location and vacation rental selection in Annapolis, Maryland! Soak in all the charm that historic Annapolis has to offer for a weekend getaway or Naval Academy events. We are in the process of adding new Annapolis vacation home rentals in time for your Summer 2019 vacation, so please be sure to check back here often for the newest selection of vacation rentals.

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Nantucket on the Chesapeake FROM $3940 - $10500

Nantucket on the Chesapeake

Annapolis
Beds: 4 | Baths: 3.5 | Sleeps: 10
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McKendree Street Mainland FROM $2889 - $8500

McKendree Street Mainland

Annapolis
Beds: 4 | Baths: 3 | Sleeps: 10
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Ben Oaks Drive FROM $5800

Ben Oaks Drive

Severna Park
Beds: 4 | Baths: 2.5 | Sleeps: 10
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22 Fleet Street FROM $2793 - $14000

22 Fleet Street

Annapolis
Beds: 3 | Baths: 2.5 | Sleeps: 6
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