Annapolis Vacation Rentals

Compare 26 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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Popular amenities for Annapolis vacation rentals

Popular
Dog-friendly Hot tub Internet
Anchors Away Abode
3 Bedroom | 2.5 Bath | Sleeps 8

Anchors Away Abode - Annapolis, MD

$418 avg / night
4.92 (13)
The Little House
2 Bedroom | 2 Bath | Sleeps 4

The Little House - Annapolis, MD

$364 avg / night
4.67 (27)
The Admiral's Retreat
6 Bedroom | 4.5 Bath | Sleeps 12

The Admiral's Retreat - Annapolis, MD

$1,637 avg / night
4.78 (9)
Anchors Aweigh
4 Bedroom | 2.5 Bath | Sleeps 8

Anchors Aweigh - Annapolis, MD

$926 avg / night
4.94 (32)
Harrison Hall
4 Bedroom | 3 Bath | Sleeps 8

Harrison Hall - Annapolis, MD

$778 avg / night
4.9 (21)

View 21 more homes

Recent Annapolis guest reviews

This was a friend getaway and it was perfect! Our stay at this beautiful VRBO in Annapolis was absolutely wonderful! The property was right on the water, offering breathtaking views that made every morning and evening feel magical. Whether sipping coffee on the deck or simply enjoying the serenity of the backyard while sitting in front of the fire pit or on the dock, the location was truly unbeatable. Close to restaurants, bars, grocery stores, and more, the location was perfect. Not too far but also not too close to the hustle and bustle. The home was impeccably clean, with every detail thoughtfully taken care of. The furniture was stylish and comfortable, and the amenities were top-notch. It felt like the perfect blend of being at a home away from home and coziness, providing everything we needed for a relaxing getaway. We did interact with customer service directly when we had questions, and they were kind and responsive. The check-in and check-out process was seamless, and all instructions were clear and easy to follow in a manual. It’s evident that great care is taken to ensure guests have a flawless experience. This property is a gem, and I highly recommend it to anyone looking for a peaceful, waterfront retreat in Annapolis. Make sure you go to the different parks and beaches. Bundle up in warm clothes if you are there during the winter months! It's well worth it!
Lori D. | Jan 2025
House was big, allowed family together time and quiet spaces to get away. Kids could romp and be noisy while other could engage in discussion or reading.
JOE H. | Jan 2025
Spacious, extremely well -appointed, clearly recently renovated. Location is very convenient to downtown, or to easy routes to other locations. All modern fixtures, lighting, heat, kitchen, etc.
William H. | Dec 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. 36 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.