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, townhouses, and more


House rentals

View 34 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

$350 avg / night
Skyline Sanctuary
2 Bedroom | 1.5 Bath | Sleeps 6

Skyline Sanctuary - Annapolis, MD

$345 avg / night
Anchors Away Abode
3 Bedroom | 2.5 Bath | Sleeps 8

Anchors Away Abode - Annapolis, MD

$407 avg / night
Admiral's Glen
3 Bedroom | 2 Bath | Sleeps 8

Admiral's Glen - Annapolis, MD

$366 avg / night
Waterside with it All
6 Bedroom | 6 Bath | Sleeps 18

Waterside with it All - Annapolis, MD

$1,150 avg / night

View 30 more homes

Recent Annapolis vacation rental reviews

During the week of Thanksgiving at this place with the family, I smiled a lot just watching everyone have a memorable time.
Jeff P. | Nov 2023
Magnificent water views
Nancy K. | Nov 2023
What a lovely location for a spacious home with some nice amenities for a larger group or family. Overall, we had a nice stay. The listing and the contents of the house could benefit from some updating. The cable TV didn’t come “as advertised” - a bit of a downer for the football watchers in our group over the Thanksgiving holiday. The photos indicated a 2nd kitchen downstairs - but we realized after we got there that it wasn’t available for our use despite being shown in the property photos. The main level had been decorated for the holidays, which was nice. The hot tub was perfect on a crisp November evening, the neighborhood was walkable & family friendly, and the views from the patio & decks are spectacular!!
Mary Beth T. | Nov 2023
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. 44 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.