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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.

Home Away from Home
SUPERHOST
Private room · 1 guest · 1 bed · 1 private bath

Home Away from HomeA furnished room with private bathroom and large closet in a quiet neighborhood near shopping, I-97, and BWI, in the home of a loving, caring, cultured, religious, and educated family. Separate small fridge, microwave, toaster, coffee maker & plenty of street parking only 20 steps from the private entrance.

Detached bedroom, private entrance, en-suite bath!
SUPERHOST
Private 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).

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

Charming Row House in Historic DistrictSip 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.

Vacation rentals for every style

Get the amount of space that is right for you

  • Homes
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  • Unique stays

Popular amenities for Annapolis vacation rentals

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

Other great vacation rentals in Annapolis

Sunny Spot Suite, Spacious & Serene,near Annapolis
SUPERHOSTEntire guest suite
Sunny Spot Suite, Spacious & Serene,near Annapolis
Price:GYD11,034 / night
GO NAVY! Gorgeous! Next to USNA
SUPERHOSTEntire house
GO NAVY! Gorgeous! Next to USNA
Price:GYD115,557 / night
South River Park Apartment
SUPERHOSTEntire guest suite
South River Park Apartment
Price:GYD18,341 / night
Cape St Claire waterfront getaway
SUPERHOSTEntire guesthouse
Cape St Claire waterfront getaway
Price:GYD25,348 / night
Wright’s Cottage- No cleaning fees! Pets! River!
SUPERHOSTEntire house
Wright’s Cottage- No cleaning fees! Pets! River!
Price:GYD22,962 / night
Howard's Cove Retreat
SUPERHOSTPrivate room
Howard's Cove Retreat
Price:GYD14,911 / night
Renovated Annapolis Row House a Minute's Walk to USNA
PLUSEntire house
Renovated Annapolis Row House a Minute's Walk to USNA
Price:GYD35,636 / night
Step Out to Main Street From a Chic Loft
PLUSEntire loft
Step Out to Main Street From a Chic Loft
Price:GYD29,613 / night
Garden Apartment Near Annapolis
SUPERHOSTEntire apartment
Garden Apartment Near Annapolis
Price:GYD14,433 / night
Wall to Wall Cool- Filled with Original Art and Sculpture
PLUSEntire apartment
Wall to Wall Cool- Filled with Original Art and Sculpture
Price:GYD23,797 / night
Stay aboard the S/V MY STUDIO on Annapolis Harbor
SUPERHOSTBoat
Stay aboard the S/V MY STUDIO on Annapolis Harbor
Price:GYD29,536 / night
Our Annapolis Penthouse
SUPERHOSTEntire guest suite
Our Annapolis Penthouse
Price:GYD22,217 / night
Show all

Learn more about Annapolis

Are there houses with pools?

Who doesn’t want a pool at their house? Here in Annapolis, you’ll find 30 houses that have pools.

What kid-friendly activities are there to do in Annapolis?

Locals agree—these are all great places to take the kids:

  • Iron Rooster- Annapolis
  • Sandy Point State Park
  • Cantler's Riverside Inn
  • Carrol's Creek Cafe
  • Boatyard Bar & Grill

What are the top places to eat in Annapolis?

Whether you’re looking for a tasty treat or a hearty meal, here’s where the locals say to go:

  • Vin 909 Winecafe
  • Boatyard Bar & Grill
  • Rams Head Tavern
  • Davis's Pub
  • Iron Rooster- Annapolis