Annapolis Vacation Rentals

Compare 34 vacation rentals with savings up to 30% off this summer.
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, townhouses, and more


House rentals

View 33 House rentals


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Annapolis vacation rentals for every getaway

Dog-friendly Hot tub Internet
The King's Court
4 Bedroom | 3.5 Bath | Sleeps 8

The King's Court - Annapolis, MD

$539 avg / night
Harrison Hall
4 Bedroom | 3 Bath | Sleeps 8

Harrison Hall - Annapolis, MD

$758 avg / night
Waterside with it All
6 Bedroom | 6 Bath | Sleeps 18

Waterside with it All - Annapolis, MD

$1,245 avg / night
The Ship's Bridge
4 Bedroom | 3.5 Bath | Sleeps 10

The Ship's Bridge - Annapolis, MD

$821 avg / night
Seas The Bay
4 Bedroom | 2 Bath | Sleeps 10

Seas The Bay - Annapolis, MD

$789 avg / night

View 29 more homes

Recent Annapolis vacation rental reviews

The Liberty Club: Beautiful home, landscaping, located in a beautiful setting-providing a temperature controlled pool and plenty of room for a family gathering. Amenities were fabulous and the weather was perfect for a family of 8 to enjoy family meals Al fresco as well as inside. We enjoyed lounging in/by the pool and warming up in the evenings by the huge gas fire pit and even took a few soaks in the hot tub. In the mornings we stretched out on the screened porch and back deck to savor our coffee and there’s plenty of room for a game of cards and family games throughout the home. This home is also very close to The Yard, close to Grauls Grocery, Naval Bagels, the USNA Stadium and various take out food places. Also in a nice walkable neighborhood for exercise. It was absolutely perfect for USNA Commissioning Week!
Noland And Chandler D. | May 2023
Furnishings and history with such a wonderful location….. aaand parking in the historic district. Wonderful home.
Matthew M. | May 2023
What is not to love? Location location location . Walking / stumbling distance from everything downtown Annapolis has to offer. As a yacht dealer, the perfect location while I am working the show. No Uber or shuttles needed, just walk out the door and walk into the show!
Bob R. | May 2023
Annapolis vacation rental FAQ

Yes, 11 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. 42 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.