Annapolis Vacation Rentals

Compare 27 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

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Condo rentals

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Townhouses

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Annapolis vacation rentals for every getaway

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

The Little House - Annapolis, MD

$496 avg / night
4.67 (27)
Anchors Away Abode
3 Bed | 2.5 Bath | Sleeps 8

Anchors Away Abode - Annapolis, MD

$559 avg / night
4.92 (13)
Seas The Bay
4 Bed | 2 Bath | Sleeps 10

Seas The Bay - Annapolis, MD

$1,182 avg / night
4.86 (7)
Blue Angel's Nest
4 Bed | 3.5 Bath | Sleeps 10

Blue Angel's Nest - Annapolis, MD

$1,071 avg / night
4.92 (37)
The Pearl of Oyster Harbor
3 Bed | 2 Bath | Sleeps 8

The Pearl of Oyster Harbor - Annapolis, MD

$691 avg / night
4.65 (23)

View 22 more homes

Recent Annapolis vacation rental reviews

very charming and clean. great location
Lana M. | Dec 2024
The Little House was perfect for our weekend trip to Annapolis and Washington DC. Cozy and warm. Walkable to everywhere in Annapolis. We’ll be back!
Kim B. | Dec 2024
The property was really good. Location was really good too. Loved the amenities of the property too. Had everything we needed plus a grill, patio, yard, and board games. The owner also had the AV already set up with YouTube TV, Netflix, etc. The only things we did not like were the temperature was difficult to get consistent through the property and there was no toilet downstairs.
CEDRIC R. | Dec 2024
Annapolis Frequently Asked Questions

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. 37 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.