Annapolis Vacation Rentals

Compare 35 vacation rentals.
USA > Maryland > Annapolis

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, condo rentals, townhouses, and more


House rentals

View 33 House rentals

Condo rentals

View 1 Condo rentals


View 1 Townhouses

Annapolis vacation rentals for every getaway

Dog-friendly Hot tub Internet
The Little House
2 Bedroom | 2 Bath | Sleeps 4

The Little House - Annapolis, MD

$322 avg / night
Harrison Hall
4 Bedroom | 3 Bath | Sleeps 8

Harrison Hall - Annapolis, MD

$641 avg / night
Anchors Away Abode
3 Bedroom | 2.5 Bath | Sleeps 8

Anchors Away Abode - Annapolis, MD

$395 avg / night
The Robins Nest
4 Bedroom | 2 Bath | Sleeps 10

The Robins Nest - Annapolis, MD

$697 avg / night
USNA Getaway
1 Bedroom | 1 Bath | Sleeps 6 (1 Adults Max)

USNA Getaway - Annapolis, MD

$214 avg / night

View 30 more homes

Recent Annapolis vacation rental reviews

I’m glad the nightly rate to this house was reasonably priced being in the winter months. It was a cute home inside. I loved the gas fireplace especially since temps outside were in the 20’s! Even though old furniture in main rooms -it was very clean which was most important to me! Pretty kitchen with new appliances. Very nice view in back of home of the Oyster creek. It’s only about 14min car ride into Annapolis downtown, which was convenient for us.
Therese H. | Feb 2024
Has pretty much everything needed for the Stay. Great location in a quiet neighborhood.
David H. | Feb 2024
The house is exactly as advertised and worked very well for our party of 5 adult friends. The location is perfect and walkable to many cute shops, marinas, and restaurants. We enjoyed our stay and would definitely rent the house again.
Wendy M. | Feb 2024
Annapolis vacation rental FAQ

Yes, 13 of our Annapolis homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 45 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.