Annapolis Vacation Rentals

Compare 24 vacation rentals.
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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 22 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

$398 avg / night
4.67 (30)
Harrison Hall
4 Bedroom | 3 Bath | Sleeps 8

Harrison Hall - Annapolis, MD

$831 avg / night
4.9 (21)
USNA Getaway
1 Bedroom | 1 Bath | Sleeps 6

USNA Getaway - Annapolis, MD

$313 avg / night
4.91 (11)
Anchors Aweigh
4 Bedroom | 2.5 Bath | Sleeps 8

Anchors Aweigh - Annapolis, MD

$964 avg / night
4.94 (32)
Porter Point
4 Bedroom | 4 Bath | Sleeps 12

Porter Point - Annapolis, MD

$906 avg / night
5.0 (1)

View 19 more homes

Browse more vacation rental amenities in Annapolis

Pool | Electric vehicle charger | Lake view | Lakefront | Riverfront | Water view | Waterfront | A/C | Elevator | Fireplace

Recent Annapolis guest reviews

This Annapolis property exceeded our expectations! Nestled in a peaceful, safe neighborhood with a small park directly across the street (perfect for children), Anchors Away Abode provided an ideal retreat during our recent visit. The home was well maintained—kitchen, bathrooms, and bedrooms all clean and exactly as represented in the property photos. The kitchen was well-stocked with all the essentials we needed to prepare most of our meals at home, saving us time and money during our stay. The fully fenced backyard would be wonderful for pets, though we didn't bring one on this trip. What truly elevated our experience were the thoughtful touches: a well-stocked coffee bar inside and a delightful outdoor area featuring a gas fire pit illuminated by string lights—perfect for evening relaxation. Access was seamless thanks to the convenient keypad entry system, allowing us to check in at our convenience. The driveway comfortably accommodates two vehicles, eliminating any parking concerns. Potential guests should note there are a few stairs leading into the home and two bedrooms located on the second floor, which might be a consideration for those with mobility limitations. The neighborhood is genuinely quiet with minimal traffic, allowing for peaceful evenings and restful sleep. We chose this location as our base while exploring Washington DC and Baltimore. Being centrally located allowed us to enjoy the calm of Annapolis while still accessing the major cities (about an hour's drive to DC, with typical metropolitan traffic). The host's communication was exceptional—responsive, helpful, and attentive throughout our stay. I wholeheartedly recommend Anchors Away Abode for anyone seeking comfort, convenience, and charm in the Annapolis area!
katie S. | Apr 2025
Everything.
Paul H. | Mar 2025
Close to everything.
Karen M. | Mar 2025
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. 34 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

Nearby destinations

Arnold   |   Edgewater   |   Crownsville   |   Severna Park   |   Shady Side   |   Pasadena   |   West River   |   Chester   |   Odenton   |   Glen Burnie   |   Grasonville   |   Bowie   |   Upper Marlboro   |   North Beach   |   Owings   |   New Carrollton   |   Landover   |   Baltimore   |   Capitol Heights   |   College Park   |   Hyattsville   |   Easton   |   Parkville   |   Takoma Park   |   Silver Spring   |   Oxon Hill   |   Maryland
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