Annapolis Vacation Rentals

Compare 16 vacation rentals.
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Make Annapolis your next getaway

Claim your spot in Maryland’s capital city with Annapolis vacation rentals. This seaside city offers a chance to admire historical architecture, tour maritime museums, and fill up on seafood. Discover something new along the east coast. 

Explore Annapolis house rentals, townhouses, and more

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House rentals

View 15 House rentals
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Townhouses

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Annapolis vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Ogelton Overlook
5 Bed | 5.5 Bath | Sleeps 14

Ogelton Overlook - Annapolis, MD

$1,855 avg / night
(excludes fees and taxes)
The Little House
2 Bed | 2 Bath | Sleeps 4

The Little House - Annapolis, MD

$467 avg / night
(excludes fees and taxes)
5.0 (5)
The Salty Crab
3 Bed | 3.5 Bath | Sleeps 10

The Salty Crab - Annapolis, MD

$849 avg / night
(excludes fees and taxes)
4.8 (5)
Anchors Aweigh
4 Bed | 2.5 Bath | Sleeps 8

Anchors Aweigh - Annapolis, MD

$1,076 avg / night
(excludes fees and taxes)
4.6 (5)
Master Shipwright
4 Bed | 4.5 Bath | Sleeps 10

Master Shipwright - Annapolis, MD

$1,766 avg / night
(excludes fees and taxes)
4.8 (5)

View 11 more homes

Recent Annapolis vacation rental reviews

Loved everything about this place. Perfect size for out needs. Easy walk to every place we wanted to go...the Naval Academy, the Harbor, shopping. The perfect spot
Lisa S. | Feb 2026
We loved this beautiful house...parking onsite and the ability to walk into Annapolis were huge pluses. We spent lots of family time by the fireplace and learned we have a couple of budding pianists in the family. What fun!
Jennifer P. | Feb 2026
Great Location and accommodations. The House does need hangers (not one was provided) and hooks to hang bath towels. Thank goodness there was one set of wall hooks in the upstairs bedroom and others elsewhere could definitely help.
SHARON, C. | Dec 2025
Annapolis Frequently Asked Questions

Yes. 20 of our Annapolis vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Annapolis vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Annapolis team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Annapolis, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Explore our Annapolis, MD, vacation rentals

Take in the sights of Chesapeake Bay with Annapolis vacation rentals. Maryland’s capital city lies about 45 minutes from both Washington D.C. and Baltimore, making it the perfect home base for exploring the east coast. Spend your afternoons hopping from museum tour to farmers market, then wind down your evenings enjoying a stroll along the waterfront. 

Take a step through time at the William Paca House & Garden, reel in a catch at Sandy Point State Park, or enjoy a fresh crab dinner at one of the many mom-and-pop seafood restaurants dotting the coast. If you’re interested in daytripping, Baltimore’s harbor hosts historic warships and museums, and nearby D.C. famously boasts a number of national landmarks. Book your stay and start your adventure.

Annapolis vacation rental inspiration 

USNA Commissioning Week rentals