Annapolis Vacation Rentals

Compare 15 vacation rentals.
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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. 

Top Annapolis property types

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House rentals

View 14 House rentals
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Townhouses

View 1 Townhouses

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

$150 avg / night
(excludes fees and taxes)
4.7 (37)
Harrison Hall
4 Bedroom | 3 Bath | Sleeps 8

Harrison Hall - Annapolis, MD

$200 avg / night
(excludes fees and taxes)
4.93 (29)
The Ship's Bridge
4 Bedroom | 3.5 Bath | Sleeps 10

The Ship's Bridge - Annapolis, MD

$550 avg / night
(excludes fees and taxes)
4.93 (59)
The Admiral's Retreat
6 Bedroom | 4.5 Bath | Sleeps 12

The Admiral's Retreat - Annapolis, MD

$1,454 avg / night
(excludes fees and taxes)
4.82 (11)
Skyline Sanctuary
2 Bedroom | 1.5 Bath | Sleeps 6

Skyline Sanctuary - Annapolis, MD

$275 avg / night
(excludes fees and taxes)
5.0 (6)

View 10 more homes

Recent Annapolis guest reviews

We loved this beautiful house...parking onsite and the ability to walk into Annapolis were huge pluses. We spent lots of family time by the fireplace and learned we have a couple of budding pianists in the family. What fun!
Jennifer P. | Feb 2026
Great Location and accommodations. The House does need hangers (not one was provided) and hooks to hang bath towels. Thank goodness there was one set of wall hooks in the upstairs bedroom and others elsewhere could definitely help.
SHARON, C. | Dec 2025
Seas the Bay is a wonderful property, immaculate and welcoming! It is ideally located in an upscale area in downtown Annapolis. You can walk to many of the town’s highlights, restaurants and shops. The space is fantastic for families or for a multiple couples trip. It is also pup friendly. The beds are extremely comfortable and the living space and kitchen are well laid out. The backyard garden and deck areas are welcoming and complemented by the finest outdoor furniture. The home is truly a gem in downtown Annapolis!
Francey B. | Dec 2025
Annapolis vacation rental FAQ

Yes. 19 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