Annapolis Vacation Rentals

Compare 23 vacation rentals.
1 Guest
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 21 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

$371 avg / night
(excludes fees and taxes)
4.66 (32)
Anchors Away Abode
3 Bedroom | 2.5 Bath | Sleeps 8

Anchors Away Abode - Annapolis, MD

$400 avg / night
(excludes fees and taxes)
4.94 (16)
Porter Point
4 Bedroom | 4 Bath | Sleeps 12

Porter Point - Annapolis, MD

$689 avg / night
(excludes fees and taxes)
4.0 (3)
Skyline Sanctuary
2 Bedroom | 1.5 Bath | Sleeps 6

Skyline Sanctuary - Annapolis, MD

$394 avg / night
(excludes fees and taxes)
5.0 (4)
Harrison Hall
4 Bedroom | 3 Bath | Sleeps 8

Harrison Hall - Annapolis, MD

$713 avg / night
(excludes fees and taxes)
4.91 (23)

View 18 more homes

Recent Annapolis guest reviews

Very nice and comfortable place. Love the easy to use fire pit on the deck. We will return to this property the next time we visit our Annapolis friends.
Peter D. | Jun 2025
We stayed in this home for commissioning week and it more than met our expectations! The easy walk to several restaurants as well as downtown Annapolis and the Naval Academy was very helpful; allowing us to avoid traffic and parking issues during this high traffic week. We appreciated being away from the noise of downtown. The home was spacious and comfortable. The kitchen has many appliances which made cooking easy. The Vacasa local operations manager was very responsive and welcoming; will definitely look for Vacasa managed properties in the future! Check-in was easy. We understand the reasoning for denying late checkout requests but were disappointed that we could not stay until 11 a.m. vs 10; many rental homes we have stayed in have later check out times.
Dan M. | May 2025
Great communication, comfortable home and super convenient .
Kathleen K. | May 2025
Annapolis vacation rental FAQ

Yes, 12 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. 33 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 the 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 problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Annapolis, log in to Trip Manager to explore the 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.

Annapolis vacation rental inspiration 

USNA Commissioning Week rentals

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