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

$328 avg / night
Anchors Away Abode
3 Bedroom | 2.5 Bath | Sleeps 8

Anchors Away Abode - Annapolis, MD

$423 avg / night
Seas The Bay
4 Bedroom | 2 Bath | Sleeps 10

Seas The Bay - Annapolis, MD

$804 avg / night
The Pearl of Oyster Harbor
3 Bedroom | 2 Bath | Sleeps 8

The Pearl of Oyster Harbor - Annapolis, MD

$466 avg / night
Anchors Aweigh
4 Bedroom | 2.5 Bath | Sleeps 8

Anchors Aweigh - Annapolis, MD

$894 avg / night

View 26 more homes

Recent Annapolis guest reviews

The home was perfect. Other than having to sweep the porches, which is expected because there was a breeze, this home was fully furnished, and everything worked as expected. Absolutely the best vacation home we have stayed in. We will be back. thank you
Jim D. | Jul 2024
This was a great house for our family. We came to Annapolis early to enjoy family time prior to dropping off our son for I-Day. The beds were comfortable and the kitchen table was perfect for dinners and cards. A grill would have been a nice touch for summer cooking. Overall, a great experience!
Amy R. | Jul 2024
Home had a great neighborhood with a great view. Spacious house with several rooms, bathrooms, and entertaining areas. Could use another hot water heater and better water pressure but overall a great experience!
Teal M. | Jun 2024
Annapolis vacation rental FAQ

Yes, 15 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. 43 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.