Annapolis, Maryland, USA skyline and State House.

Annapolis

Don’t settle for your typical hotels in Annapolis, MD. You deserve the best when it comes to your vacations — especially if you’re headed to such a remarkable destination such as this. Stay in one of our excellent Annapolis, MD, vacation rentals to make the most of your experience!

Our vacation rentals in Annapolis, Maryland, allow you to soak in all the charm that this historic area has to offer for your next weekend getaway — whether you’re looking to relax with family and friends or attend Naval Academy events. Explore the options below, and be sure to check back here often for the newest additions to our collection of beautiful rental homes on the Chesapeake Bay!

View Our Annapolis, MD, Vacation Rentals

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Nantucket on the Chesapeake FROM $3940 - $12500

Nantucket on the Chesapeake

Annapolis
Beds: 4 | Baths: 3.5 | Sleeps: 10
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McKendree Street Mainland FROM $3150 - $8500

McKendree Street Mainland

Annapolis
Beds: 4 | Baths: 3 | Sleeps: 8
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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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East Street Easy Walk FROM $1575 - $2750

East Street Easy Walk

Annapolis
Beds: 1 | Baths: 1.5 | Sleeps: 2
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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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