Annapolis Vacation Rentals

Compare 34 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 32 House rentals

Condo rentals

View 1 Condo rentals


View 1 Townhouses

Popular amenities for Annapolis vacation rentals

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

The Little House - Annapolis, MD

$344 avg / night
Anchors Away Abode
3 Bedroom | 2.5 Bath | Sleeps 8

Anchors Away Abode - Annapolis, MD

$476 avg / night
Seas The Bay
4 Bedroom | 2 Bath | Sleeps 10

Seas The Bay - Annapolis, MD

$683 avg / night
Blue Angel's Nest
4 Bedroom | 3.5 Bath | Sleeps 10

Blue Angel's Nest - Annapolis, MD

$755 avg / night
The Pearl of Oyster Harbor
3 Bedroom | 2 Bath | Sleeps 8

The Pearl of Oyster Harbor - Annapolis, MD

$467 avg / night

View 29 more homes

Recent Annapolis guest reviews

We gathered her for Mother’s day, family from OH and DE. Great location if u’d like to go sightseeing in Annapolis or DC. Also great to just chill at the house. We loved the outdoor amenities; the yard, deck and pier. Great place to play and gather and relax. The house was decorated so cute and had enough towels for everyone as well as dishes, cookware, space and games. The house also had plenty of towel hooks, hampers, and luggage racks in the bedrooms, something that many property owners don’t think about. Also loved the use of the toiletries available in each bathroom. Just bring ur clothes and enjoy the rest.
Kelly C. | May 2024
We loved our stay at this home
James R. | May 2024
The house was perfect for us - three generations were in town for a family wedding. The views are amazing, the master bedroom had its own porch and wonderful views. The basement bedroom and living area was perfect for my daughter’s family, with a small fridge that they could keep bottles in for the baby. We mostly stayed in and and cooked when we were not attending family events and the kitchen had everything we needed. The small beach across from the house was fun for my young grandson. The location is perfect, beautiful and quiet, and it is a quick drive or Uber to downtown Annapolis.
Lucy C. | May 2024
Annapolis vacation rental FAQ

Yes, 14 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.