Skip to content
25 stays

Stays in Annapolis

Enter dates and number of guests to see the total price per night.
Check travel restrictions before booking.
Please review and follow government travel guidelines.
Learn more
SUPERHOST
Houseboat in Annapolis
Condo Houseboat
4 guests2 bedrooms2 beds2 bathrooms
WifiAir conditioningKitchenFree parking
Rating 5.0 out of 5;6 reviews
SUPERHOST
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
4 guests2 bedrooms2 beds1 bathroom
WifiAir conditioningKitchen
Rating 4.94 out of 5;164 reviews
SUPERHOST
Tiny house in Annapolis
Charming home close to downtown.
6 guests2 bedrooms3 beds2 bathrooms
WifiAir conditioningKitchenFree parking
Rating 4.92 out of 5;90 reviews
SUPERHOST
Boat in Annapolis
Hunter 36' Sailboat
6 guests2 bedrooms4 beds1 bathroom
WifiAir conditioningKitchenFree parking
Rating 4.79 out of 5;119 reviews
Tiny house in Annapolis
Lil’ House - A Serene Tiny Home Experience
2 guests1 bedroom1 bed1 bathroom
WifiAir conditioningKitchenFree parking
Rating 5.0 out of 5;12 reviews
Boat in Annapolis
Glamping Aboard On Annapolis Harbor Sailboat
3 guests2 bedrooms3 beds1.5 bathrooms
WifiKitchen
SUPERHOST
Boat in Annapolis
Welcome Aboard!
4 guests2 bedrooms3 beds2 bathrooms
WifiAir conditioningKitchenFree parking
Rating 5.0 out of 5;24 reviews
SUPERHOST
Boat in Edgewater
Beautiful Waterfront Studio Yacht!
4 guests1 bedroom2 beds1 bathroom
WifiAir conditioningKitchenFree parking
Rating 4.72 out of 5;43 reviews
SUPERHOST
Private room in Annapolis
Tiny House above the Hideaway
4 guests1 bedroom2 beds1 private bathroom
WifiAir conditioningKitchenFree parking
Rating 4.78 out of 5;23 reviews
SUPERHOST
Boat in Edgewater
"Equinox" Center of the Sun
3 guests2 bedrooms2 beds2 bathrooms
Air conditioningKitchenFree parking
Rating 4.76 out of 5;67 reviews
SUPERHOST
Farm stay in Davidsonville
Quaint Cottage, on 14 acre horse farm.
4 guests1 bedroom2 beds1.5 bathrooms
WifiAir conditioningKitchenFree parking
Rating 4.71 out of 5;7 reviews
Boat in Edgewater
Floating home, fresh breezes..
2 guests1 bedroom1 bed1 bathroom
WifiAir conditioningKitchenFree parking
Rating 4.68 out of 5;50 reviews
SUPERHOST
Campsite in Annapolis
Outdoor Campsite by Navy Stadium
3 guestsStudio1 bed1 bathroom
WifiAir conditioningKitchenFree parking
Boat in Annapolis
Stay on a Boat in Annapolis-fun, sun, relax!
8 guests4 bedrooms4 beds4 bathrooms
Air conditioningKitchen
Rating 4.80 out of 5;7 reviews
Boat in Annapolis
Boat BNB Luxury Accomadations Aboard a Catamaran
6 guests3 bedrooms3 beds2 bathrooms
WifiAir conditioningKitchenFree parking
Rating 5.0 out of 5;4 reviews
SUPERHOST
Campsite in Annapolis
Campsite by the USNA Stadium
3 guests1 bedroom0 beds1 bathroom
WifiKitchenFree parking
Rating 5.0 out of 5;5 reviews
Boat in Annapolis
30ft Sailboat on the Magothy River
4 guestsStudio2 beds1 bathroom
Free parking
Boat in Annapolis
Luxury50ft Catamaran YachtAnnapolis
9 guests3 bedrooms4 beds3 bathrooms
Air conditioningKitchen
Rating 5.0 out of 5;5 reviews
Private room in Edgewater
Luxury Port Stateroom
3 guests1 bedroom3 beds1 bathroom
WifiAir conditioningKitchen
Rating 5.0 out of 5;4 reviews
Boat in Edgewater
Pa’draigi’n II at a new marina
6 guests3 bedrooms3 beds4 bathrooms
WifiAir conditioningKitchenFree parking
120 of 25 Castles
Enter dates to see full pricing. Additional fees apply. Taxes may be added.