Annapolis Vacation Rentals

Compare 34 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 Bedroom | 2 Bath | Sleeps 4

The Little House - Annapolis, MD

$321 avg / night
Anchors Away Abode
3 Bedroom | 2.5 Bath | Sleeps 8

Anchors Away Abode - Annapolis, MD

$477 avg / night
Seas The Bay
4 Bedroom | 2 Bath | Sleeps 10

Seas The Bay - Annapolis, MD

$638 avg / night
Blue Angel's Nest
4 Bedroom | 3.5 Bath | Sleeps 10

Blue Angel's Nest - Annapolis, MD

$722 avg / night
The Pearl of Oyster Harbor
3 Bedroom | 2 Bath | Sleeps 8

The Pearl of Oyster Harbor - Annapolis, MD

$421 avg / night

View 29 more homes

Recent Annapolis vacation rental reviews

This is our 2nd or 3rd time staying at this lovely home in Annapolis. A group of 8 and found the house perfectly stocked with everything we needed. The kitchen is a dream, we cooked meals together, played cards at the large dining table and lounged in front of the fireplace for morning chats. It was April and the weather was colder to start and ended up mid 70's and sunny. The private beach across the street was fun and relaxing. We brought corn hole and played for hours. We even took dips in the bay! I cannot say enough about the views! Overlooking the Bay Bridge was serene! The house has plenty of comfortable bedrooms well stocked with linens and blankets.l! In fact enough bedrooms for our group to spread out and we even used the fold out couch in the basement family room. The heating and cooling system was always spot on to keep us at a happy temp. The afternoon and evening breezes were amazing so we were lucky we didn't need to use the A/C much. Town is a quick 15 minute drive and the iron rooster pop tarts are a must. Grocery stores near by made it so easy to just spend most of our time at the house. It's decorated like a beautiful show room but thoughtfully arranged so it's comfortable and easy to feel at home. One of the nicest homes we've rented and we will definitely be back!
Brandy T. | Apr 2024
Well stocked home to enhance your vacation. Extremely clean, fantastic location.
Tiffany C. | Apr 2024
This is the place to stay if you're looking to get away. Great views and sunrises. They have kayaks, fishing poles, bicycles, out door games, fire pit, grill, and a large patio. Inside there's board games and a large Florida room in case it rains and you can't enjoy the outdoor activities. Our family had a great time hanging out, making smores, and enjoying each others company while we got to spend time together here. Everyone should stay here at least once.
Vernon D. | Apr 2024
Annapolis vacation rental FAQ

Yes, 13 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. 45 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.