Annapolis Vacation Rentals

Compare 33 vacation rentals. Enter your trip dates to get started.
USA > Maryland > Annapolis

Make Annapolis your next getaway—choose from 33 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, townhouses, and more


House rentals

View 32 House 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

$368 avg / night
The King's Court
4 Bedroom | 3.5 Bath | Sleeps 8

The King's Court - Annapolis, MD

$597 avg / night
Cozy Yellow House
2 Bedroom | 1 Bath | Sleeps 4

Cozy Yellow House - Annapolis, MD

$389 avg / night
Blue Angel's Nest
4 Bedroom | 3.5 Bath | Sleeps 10

Blue Angel's Nest - Annapolis, MD

$846 avg / night
The Pacific Fleet House
5 Bedroom | 3.5 Bath | Sleeps 10

The Pacific Fleet House - Annapolis, MD

$994 avg / night

View 28 more homes

Recent Annapolis vacation rental reviews

Great location, right by the visitor entrance to the Naval Academy. Very quiet and comfy beds.
Evelyn A. | Apr 2023
The location of this lovely Little House was perfect - close to everything. The small parking spot was a huge bonus - our Subaru Outback fit no problem, it was just really tight to open the door to get out; once we parked there we never got in again until we left - we walked everywhere! The house was very comfortable and nicely appointed. The construction across the street was a bit of a bummer - they started dumping rocks at about 6:30 am, but were generally done working by 3:30-4 pm, so we had quiet evenings watching the world go by sitting out on the little patio. They do need the construction though (our understanding is that it will have a parking garage) - parking in Annapolis seems a little nuts.
Donna J. | Apr 2023
Great location, walkable to anywhere in Eastport and Annapolis. House is exactly as pictured and has all the amenities you’d need including soaps and shampoo that you don’t always find at a vacation rental including fun yard games to enjoy the awesome backyard. We will definitely stay here next time we’re in town.
Priya G. | Apr 2023
Annapolis vacation rental FAQ

Yes, 10 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. 38 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.