Annapolis Vacation Rentals

Compare 16 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 15 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

$238 avg / night
(excludes fees and taxes)
4.69 (36)
The Master Shipwright
4 Bedroom | 4.5 Bath | Sleeps 10 (6 Adults Max)

The Master Shipwright - Annapolis, MD

$1,248 avg / night
(excludes fees and taxes)
4.93 (14)
Anchors Aweigh
4 Bedroom | 2.5 Bath | Sleeps 8

Anchors Aweigh - Annapolis, MD

$712 avg / night
(excludes fees and taxes)
4.9 (39)
The Ship's Bridge
4 Bedroom | 3.5 Bath | Sleeps 10

The Ship's Bridge - Annapolis, MD

$693 avg / night
(excludes fees and taxes)
4.93 (59)
Seas The Bay
4 Bedroom | 2 Bath | Sleeps 10

Seas The Bay - Annapolis, MD

$600 avg / night
(excludes fees and taxes)
4.83 (12)

View 11 more homes

Recent Annapolis guest reviews

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
We had a really lovely stay at this property. The house was big enough for our large family to spend Thanksgiving here and we loved the location on the water and so close to the Naval Academy. The house is obviously old and several things were in need of maintenance, but overall we still had a very nice stay.
Andrew D. | Dec 2025
This is a beautiful VRBO VACASA property, our family stay was perfect, we loved the house, it was very well equipped, we really needed very few additional items for our stay .
Royden Z. | Dec 2025
Annapolis vacation rental FAQ

Yes. 20 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