Skip to content
300+ stays

Stays in Annapolis

More than 14,000 guests have stayed in Annapolis.
On average they rated their stays 4.9 out of 5 stars.
PLUS
Entire loft in Annapolis
Step Out to Main Street From a Chic Loft
4 guests1 bedroom1 bed1 bath
WifiAir conditioningKitchen
Rating 4.88 out of 5;499 reviews
Price:$140 / night
SUPERHOST
Entire house in Annapolis
As mentioned in the Washington Post
6 guests2 bedrooms2 beds1.5 baths
WifiAir conditioningKitchen
Rating 4.80 out of 5;305 reviews
Price:$129 / night
PLUS
Entire house in Annapolis
Charming Row House in Historic District
6 guests2 bedrooms3 beds1 bath
WifiAir conditioningKitchen
Rating 4.97 out of 5;275 reviews
Price:$172 / night
Entire guest suite in Arnold
Sunny Spot Suite, Spacious & Serene,near Annapolis
3 guests1 bedroom1 bed1 bath
WifiAir conditioningFree parking
Rating 4.85 out of 5;304 reviews
Price:$54 / night
PLUS
Entire house in Annapolis
Renovated Annapolis Row House a Minute's Walk to USNA
6 guests2 bedrooms3 beds2.5 baths
WifiAir conditioningKitchen
Rating 4.98 out of 5;211 reviews
Price:$156 / night
PLUS
Entire house in Annapolis
Beautiful and Tranquil Carriage House
8 guests2 bedrooms4 beds1.5 baths
WifiAir conditioningKitchenFree parking
Rating 4.98 out of 5;132 reviews
Price:$247 / night
SUPERHOST
Entire apartment in Annapolis
COZY & UNIQUE STUDIO - HEART OF DOWNTOWN ANNAPOLIS
2 guestsStudio2 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.77 out of 5;115 reviews
Price:$105 / night
SUPERHOST
Entire apartment in Annapolis
Modern Apartment over the Heart of Main Street!
6 guests2 bedrooms2 beds1 bath
WifiAir conditioningKitchen
Rating 4.80 out of 5;227 reviews
Price:$119 / night
SUPERHOST
Entire house in Annapolis
Wright’s Cottage- No cleaning fees! Pets! River!
2 guests1 bedroom1 bed1 bath
WifiAir conditioningKitchenFree parking
Rating 4.97 out of 5;145 reviews
Price:$110 / night
SUPERHOST
Private room in Annapolis
Howard's Cove Retreat
2 guests1 bedroom2 beds1 private bath
WifiAir conditioningFree parking
Rating 4.90 out of 5;273 reviews
Price:$73 / night
SUPERHOST
Entire house in Annapolis
Newly Renovated Four Bedroom Home in Annapolis
8 guests4 bedrooms5 beds2.5 baths
WifiAir conditioningKitchenFree parking
Rating 4.80 out of 5;109 reviews
Price:$331 / night
SUPERHOST
Entire house in Annapolis
New Hotel Chic
4 guests2 bedrooms2 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.91 out of 5;85 reviews
Price:$220 / night
Entire guest suite in Annapolis
1A Annapolis Apartment
4 guests1 bedroom1 bed1 bath
WifiAir conditioningKitchenFree parking
Rating 4.66 out of 5;160 reviews
Price:$114 / night
SUPERHOST
Entire apartment in Annapolis
Brand New Reno in Historic Dist w 2 Parking spots
4 guests2 bedrooms3 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.97 out of 5;136 reviews
Price:$149 / night
Entire apartment in Annapolis
1B Annapolis Apartment
4 guests1 bedroom1 bed1 bath
WifiAir conditioningKitchenFree parking
Rating 4.68 out of 5;198 reviews
Price:$114 / night
SUPERHOST
Private room in Arnold
Detached bedroom, private entrance, en-suite bath!
2 guests1 bedroom1 bed1 private bath
WifiAir conditioningKitchenFree parking
Rating 4.96 out of 5;264 reviews
Price:$70 / night
SUPERHOST
Entire house in Edgewater
Edgewater/Mayo Getaway! **Please, no parties!!**
8 guests4 bedrooms4 beds2.5 baths
WifiAir conditioningKitchenFree parking
Rating 4.76 out of 5;112 reviews
Price:$378 / night
SUPERHOST
Entire townhouse in Annapolis
Historic Downtown Property
6 guests3 bedrooms4 beds2.5 baths
WifiAir conditioningKitchen
Rating 4.90 out of 5;159 reviews
Price:$275 / night
SUPERHOST
Entire apartment in Annapolis
King George Pied-a-Terre -A true Annapolis Retreat
3 guests1 bedroom1 bed1 bath
WifiAir conditioningKitchen
Rating 4.88 out of 5;151 reviews
Price:$128 / night
SUPERHOST
Entire apartment in Annapolis
PRIVATE DOUBLE SUITE IN THE ❤️ OF DOWNTOWN
5 guests2 bedrooms3 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.78 out of 5;54 reviews
Price:$140 / night
1 20 of 300+ places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.