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300+ stays

Stays in Annapolis

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PLUS
Entire flat in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
4 guests1 bedroom2 beds1 bathroom
WifiAir conditioningKitchenFree parking
Rating 4.93 out of 5;206 reviews
PLUS
Entire house in Annapolis
Beautiful and Tranquil Carriage House
8 guests2 bedrooms4 beds1.5 bathrooms
WifiAir conditioningKitchenFree parking
Rating 4.98 out of 5;132 reviews
SUPERHOST
Entire flat in Annapolis
COZY & UNIQUE STUDIO - HEART OF DOWNTOWN ANNAPOLIS
2 guestsStudio2 beds1 bathroom
WifiAir conditioningKitchenFree parking
Rating 4.79 out of 5;110 reviews
SUPERHOST
Entire house in Annapolis
Wright’s Cottage- No cleaning fees! Pets! River!
2 guests1 bedroom1 bed1 bathroom
WifiAir conditioningKitchenFree parking
Rating 4.97 out of 5;145 reviews
SUPERHOST
Private room in Annapolis
Howard's Cove Retreat
2 guests1 bedroom2 beds1 private bathroom
WifiAir conditioningFree parking
Rating 4.90 out of 5;272 reviews
SUPERHOST
Entire house in Annapolis
Newly Renovated Four Bedroom Home in Annapolis
8 guests4 bedrooms5 beds2.5 bathrooms
WifiAir conditioningKitchenFree parking
Rating 4.80 out of 5;109 reviews
SUPERHOST
Entire flat in Edgewater
Waterfront Annapolis Apartment! (South River)
8 guests4 bedrooms8 beds2 bathrooms
WifiAir conditioningKitchenFree parking
Rating 4.85 out of 5;130 reviews
SUPERHOST
Entire house in Annapolis
New Hotel Chic
4 guests2 bedrooms2 beds1 bathroom
WifiAir conditioningKitchenFree parking
Rating 4.90 out of 5;81 reviews
Entire guest suite in Annapolis
1A Annapolis Apartment
4 guests1 bedroom1 bed1 bathroom
WifiAir conditioningKitchenFree parking
Rating 4.65 out of 5;159 reviews
SUPERHOST
Entire flat in Annapolis
Brand New Reno in Historic Dist w 2 Parking spots
4 guests2 bedrooms3 beds1 bathroom
WifiAir conditioningKitchenFree parking
Rating 4.97 out of 5;134 reviews
Entire flat in Annapolis
1B Annapolis Apartment
4 guests1 bedroom1 bed1 bathroom
WifiAir conditioningKitchenFree parking
Rating 4.68 out of 5;198 reviews
SUPERHOST
Private room in Arnold
Detached bedroom, private entrance, en-suite bath!
2 guests1 bedroom1 bed1 private bathroom
WifiAir conditioningKitchenFree parking
Rating 4.97 out of 5;263 reviews
SUPERHOST
Entire house in Edgewater
Edgewater/Mayo Getaway! **Please, no parties!!**
8 guests4 bedrooms4 beds2.5 bathrooms
WifiAir conditioningKitchenFree parking
Rating 4.79 out of 5;110 reviews
SUPERHOST
Entire guest suite in Annapolis
Our Annapolis Penthouse
3 guests1 bedroom2 beds1 bathroom
WifiAir conditioningFree parking
Rating 4.97 out of 5;184 reviews
SUPERHOST
Private room in Annapolis
Chesapeake Mornings
2 guests1 bedroom1 bed1.5 bathrooms
WifiAir conditioningKitchenFree parking
Rating 4.91 out of 5;151 reviews
SUPERHOST
Entire house in Annapolis
Modern Waterfront: Quiet but close to Everything.
12 guests5 bedrooms5 beds4 bathrooms
WifiAir conditioningKitchenFree parking
Rating 4.98 out of 5;41 reviews
SUPERHOST
Entire guest house in Riva
The Riva House
2 guests1 bedroom1 bed1 bathroom
WifiAir conditioningKitchenFree parking
Rating 4.99 out of 5;107 reviews
SUPERHOST
Entire flat in Annapolis
Gybeset Eastport Inn
5 guests3 bedrooms3 beds1 bathroom
WifiAir conditioningKitchenFree parking
Rating 4.84 out of 5;121 reviews
SUPERHOST
Entire house in Annapolis
Charming Renovated Historic Home Downtown wparking
6 guests3 bedrooms5 beds2 bathrooms
WifiAir conditioningKitchenFree parking
Rating 4.91 out of 5;81 reviews
Entire flat in Annapolis
English Apartment close to Downtown
5 guests2 bedrooms3 beds1 bathroom
WifiAir conditioningFree parking
Rating 4.74 out of 5;117 reviews
120 of 300+ places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.