Skip to content
Sign up
Log in
Vacation rentals in Annapolis

Vacation rentals in Annapolis

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Annapolis

Guests agree: these stays are highly rated for location, cleanliness, and more.

Charming Row House in Historic District
PLUSEntire house · 6 guests · 3 beds · 1 bath
Charming Row House in Historic District

Sip morning coffee beneath a shady parasol on the wooden rear deck overlooking a garden attached to this charming row house. Inside, polished wooden floorboards lend warmth to the homey interior. The front porch hosts a red rocking chair.

What guests are saying:

“We loved our stay at this beautiful property. The place is tastefully decorated. You feel immediately at home and have everything you need. It was spotless clean. Then there is the gradual discovery of the area. Right down the street, there is a charming community garden on the water, A great place to have your morning coffee, or evening sunset gazing. The neighbourhood is great for walking and just a few blocks away from the historic town center. And of course they provide bikes to make exploring easy and fun! Sean was an amazingly host- very helpful and communicative. We can’t wait to go back!”

Detached bedroom, private entrance, en-suite bath!
SUPERHOSTPrivate room · 2 guests · 1 bed · 1 private bath
Detached bedroom, private entrance, en-suite bath!

Our place is close to historic Annapolis, the Naval Academy (7 min by car), and Sandy Point State Park (12 minutes by car). The house is in a quiet neighborhood, the location is convenient for day trips to Baltimore or Washington DC and Annapolis itself is beautiful. Our place is good for couples, solo adventurers, business travelers, and families (with kids).

What guests are saying:

“Very accommodating, always attentive, fresh sheets/bath towels on a weekly basis. Lovely kitchen with eating area. Bathroom is large with roomy closet space. Lovely area in Maryland to stay in with access to many parks, waterways and activities. Would stay here again.”

Renovated Annapolis Row House a Minute's Walk to USNA
PLUSEntire house · 6 guests · 3 beds · 2.5 baths
Renovated Annapolis Row House a Minute's Walk to USNA

Make no mistake that this nautically themed house is close to the Naval Academy. Original details have been preserved, such as the charming front porch and interior millwork. A thoughtful renovation has created a luxurious new kitchen and bathrooms.

What guests are saying:

“This house is so charming. From the moment you walk in, you feel welcomed and at home. The nautical decor is stunning and knocked this Navy mil spouse’s socks off! I have serious envy for every piece they own. The house is clean and all amenities are modern and high end. The bedrooms and bathrooms are spacious. They also have everything you need to cook your own meals. I was so happy that it was only a 2 minute walk to our favorite downtown coffee shop (Bitty & Beau’s) and our favorite brunch spot (Iron Rooster). If you are going on USNA, it is less than a five minute walk. Super convenient!! The next time we are in town for a function, we will be staying here!”

Vacation rentals for every style

Get the amount of space that is right for you

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Annapolis vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Annapolis

Step Out to Main Street From a Chic Loft
PLUSEntire loft
Step Out to Main Street From a Chic Loft
Price:ﺩ.ﺇ 542 / night
GO NAVY! Gorgeous! Next to USNA
SUPERHOSTEntire house
GO NAVY! Gorgeous! Next to USNA
Price:ﺩ.ﺇ 2,388 / night
Our Annapolis Penthouse
SUPERHOSTEntire guest suite
Our Annapolis Penthouse
Price:ﺩ.ﺇ 417 / night
Howard's Cove Retreat
SUPERHOSTPrivate room
Howard's Cove Retreat
Price:ﺩ.ﺇ 260 / night
Garden Apartment Near Annapolis
SUPERHOSTEntire apartment
Garden Apartment Near Annapolis
Price:ﺩ.ﺇ 254 / night
Wall to Wall Cool- Filled with Original Art and Sculpture
PLUSEntire apartment
Wall to Wall Cool- Filled with Original Art and Sculpture
Price:ﺩ.ﺇ 420 / night
Sunny Spot Suite, Spacious & Serene,near Annapolis
SUPERHOSTEntire guest suite
Sunny Spot Suite, Spacious & Serene,near Annapolis
Price:ﺩ.ﺇ 194 / night
South River Park Apartment
SUPERHOSTEntire guest suite
South River Park Apartment
Price:ﺩ.ﺇ 359 / night
Wright’s Cottage- No cleaning fees! Pets! River!
SUPERHOSTEntire house
Wright’s Cottage- No cleaning fees! Pets! River!
Price:ﺩ.ﺇ 401 / night
Stay aboard the S/V MY STUDIO on Annapolis Harbor
SUPERHOSTBoat
Stay aboard the S/V MY STUDIO on Annapolis Harbor
Price:ﺩ.ﺇ 495 / night
Cape St Claire waterfront getaway
SUPERHOSTEntire guesthouse
Cape St Claire waterfront getaway
Price:ﺩ.ﺇ 441 / night
Brand New Reno in Historic Dist w 2 Parking spots
SUPERHOSTEntire apartment
Brand New Reno in Historic Dist w 2 Parking spots
Price:ﺩ.ﺇ 513 / night
Show all