Annapolis Vacation Rentals

Compare 30 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 28 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

$322 avg / night 4.65 (20)
Anchors Away Abode
3 Bedroom | 2.5 Bath | Sleeps 8

Anchors Away Abode - Annapolis, MD

$406 avg / night 4.89 (9)
Seas The Bay
4 Bedroom | 2 Bath | Sleeps 10

Seas The Bay - Annapolis, MD

$781 avg / night 4.67 (3)
The Pearl of Oyster Harbor
3 Bedroom | 2 Bath | Sleeps 8

The Pearl of Oyster Harbor - Annapolis, MD

$467 avg / night 4.78 (18)
Anchors Aweigh
4 Bedroom | 2.5 Bath | Sleeps 8

Anchors Aweigh - Annapolis, MD

$874 avg / night 4.93 (27)

View 25 more homes

Recent Annapolis guest reviews

Location was perfect and this house was in the heart of it all! Great for a relaxing getaway. One of our favorite vacation homes we’ve ever stayed at.
Todd H. | Aug 2024
Great amount of space for all, pool was awesome for those 80 degree days. Outdoor eating area fit us all with great views of the Bay.
Grace M. | Aug 2024
LOVE, LOVE the location - everything is walkable- St John's, USNA, the Capitol, Main Street, and the City Dock.
Elizabeth R. | Aug 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. 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.