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300+ places to stay

Plus
Entire apartment
Wall to Wall Cool- Filled with Original Art and Sculpture
4 guests1 bedroom2 beds1 bath
WifiFree parkingKitchenHeating
Includes cancellation flexibility
Price:$75 / night
Plus
Entire loft
Step Out to Main Street From a Chic Loft
4 guests1 bedroom1 bed1 bath
WifiKitchenHeating
Includes cancellation flexibility
Price:$99 / night
SUPERHOST
Entire house
As mentioned in the Washington Post
6 guests2 bedrooms2 beds1.5 baths
WifiKitchenHeating
Price:$80 / night
Plus
Entire house
Charming Row House in Historic District
6 guests2 bedrooms3 beds1 bath
WifiKitchenHeating
Includes cancellation flexibility
Price:$89 / night
SUPERHOST
Entire guesthouse
Chesapeake Birdhouse Studio
2 guests1 bedroom1 bed1 bath
WifiHeating
Price:$135 / night
Entire apartment
1A Annapolis Apartment
4 guests1 bedroom1 bed1 bath
WifiFree parkingKitchenHeating
Price:$75 / night
SUPERHOST
Private room
Basement apartment in Heart of Eastport! : )
2 guests1 bedroom2 beds1 private bath
WifiFree parkingKitchenHeating
Price:$60 / night
SUPERHOST
Entire apartment
Modern Apartment over the Heart of Main Street!
6 guests2 bedrooms2 beds1 bath
WifiKitchenHeating
Includes cancellation flexibility
Price:$99 / night
SUPERHOST
Private room
Pet Friendly Light House
2 guests1 bedroom1 bed1 bath
WifiFree parkingKitchen
Includes cancellation flexibility
Price:$45 / night
SUPERHOST
Entire guest suite
Charming Downtown Annapolis Studio
2 guests1 bedroom1 bed1 bath
WifiHeating
Includes cancellation flexibility
Price:$79 / night
SUPERHOST
Private room
Eastport studio apartment! : )
2 guestsStudio2 beds1 private bath
WifiFree parkingHeating
Price:$60 / night
SUPERHOST
Entire apartment
COZY & UNIQUE STUDIO - HEART OF DOWNTOWN ANNAPOLIS
2 guestsStudio2 beds1 bath
WifiFree parkingKitchenHeating
Includes cancellation flexibility
Price:$53 / night
SUPERHOST
Entire apartment
Gybeset Eastport Inn
5 guests3 bedrooms3 beds1 bath
WifiFree parkingKitchenHeating
Includes cancellation flexibility
Price:$101 / night
SUPERHOST
Entire apartment
PRIVATE DOUBLE SUITE IN THE ❤️ OF DOWNTOWN
5 guests2 bedrooms3 beds1 bath
WifiFree parkingKitchenHeating
Includes cancellation flexibility
Price:$65 / night
SUPERHOST
Entire apartment
Charming Eastport
2 guests1 bedroom1 bed1 bath
WifiFree parkingKitchenHeating
Includes cancellation flexibility
Price:$125 / night
SUPERHOST
Entire house
New Hotel Chic
4 guests2 bedrooms2 beds1 bath
WifiFree parkingKitchenHeating
Includes cancellation flexibility
Price:$220 / night
SUPERHOST
Entire apartment
Adorable Annapolis Apartment!
2 guests1 bedroom1 bed1 bath
WifiFree parkingKitchenHeating
Includes cancellation flexibility
Price:$135 / night
Plus
Entire house
Renovated Annapolis Row House a Minute's Walk to USNA
6 guests2 bedrooms3 beds2.5 baths
WifiKitchenHeating
Includes cancellation flexibility
Price:$99 / night
SUPERHOST
Entire apartment
The Bennett House
6 guests2 bedrooms3 beds1 bath
WifiKitchenHeating
Includes cancellation flexibility
Price:$130 / night
Plus
Entire cottage
Enchanting Waterfront Cottage in Eastport
2 guests1 bedroom1 bed1 bath
WifiFree parkingKitchenHeating
Includes cancellation flexibility
Price:$259 / night
1 20 of 300+ places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.