Annapolis Vacation Rentals

Compare 35 vacation rentals. Enter your trip dates to get started.
USA > Maryland > Annapolis

Make Annapolis your next getaway—choose from 35 great vacation rentals

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, and more


House rentals

View 35 House rentals

Annapolis vacation rentals for every getaway

Dog-friendly Hot tub Internet
The Ship's Bridge
4 Bedroom | 3.5 Bath | Sleeps 10

The Ship's Bridge - Annapolis, MD

$959 avg / night
Blue Angel's Nest
4 Bedroom | 3.5 Bath | Sleeps 10

Blue Angel's Nest - Annapolis, MD

$900 avg / night
The Pacific Fleet House
5 Bedroom | 3.5 Bath | Sleeps 10

The Pacific Fleet House - Annapolis, MD

$1,110 avg / night
Anchors Aweigh
4 Bedroom | 2.5 Bath | Sleeps 8

Anchors Aweigh - Annapolis, MD

$966 avg / night
Base Camp on the Lake
6 Bedroom | 4.5 Bath | Sleeps 16

Base Camp on the Lake - Annapolis, MD

$1,338 avg / night

View 30 more homes

Recent Annapolis vacation rental reviews

The house was so nice, clean and welcoming!! It was very comparable and had great amenities too! We would be interested in staying here again when we come to visit our son. The owners were super kind and generous as well!
Kimberle S. | Aug 2022
Very comfortable! A home away from home.
Patricia E. | Jul 2022
The house is beautiful and spacious. The kitchen is very well equipped. The appliances are so new and modern I had to figure how to use some. The outside is incredibly quiet and peaceful. Highly recommended.
Charlene H. | Jul 2022
Annapolis Frequently Asked Questions

Yes, 9 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. 41 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.