Annapolis Vacation Rentals

Compare 31 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

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House rentals

View 29 House rentals
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Condo rentals

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Townhouses

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Popular amenities for Annapolis vacation rentals

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

The Little House - Annapolis, MD

$347 avg / night
Anchors Away Abode
3 Bedroom | 2.5 Bath | Sleeps 8

Anchors Away Abode - Annapolis, MD

$478 avg / night
Seas The Bay
4 Bedroom | 2 Bath | Sleeps 10

Seas The Bay - Annapolis, MD

$729 avg / night
Blue Angel's Nest
4 Bedroom | 3.5 Bath | Sleeps 10

Blue Angel's Nest - Annapolis, MD

$500 avg / night
The Pearl of Oyster Harbor
3 Bedroom | 2 Bath | Sleeps 8

The Pearl of Oyster Harbor - Annapolis, MD

$475 avg / night

View 26 more homes

Recent Annapolis guest reviews

My family of 6 came to Annapolis for our retirement ceremony and loved this property. It was immaculate, perfectly located (if you don't have/need a car), and gave us access to all the things we wanted to do and see with minimal trval time. The owners clearly care very much for the property, and have done a fantastic job updating it even in the historic district. Any renter should be aware - if you have difficulty with stairs, the master is on the 3rd floor, so there's come climbing to do.
Todd S. | Jun 2024
We enjoyed our stay:). Location was perfect and we will definitely return.
Jill S. | Jun 2024
Beautiful home with lots of light and space. The best part is the view of the bay at sunrise! My family had a great time swimming and fishing off the beach.
Kasey C. | Jun 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. 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.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons 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.