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.
Entire apartment in Annapolis
Awesome downtown Annapolis location!
4 guests1 bedroom2 beds1 bath
Free parkingWifiKitchenAir conditioning
$160 per night
SUPERHOST
Entire guest suite in Arnold
Sunny Spot Suite, Spacious & Serene,near Annapolis
3 guests1 bedroom2 beds1 bath
Free parkingWifiAir conditioning
$56 per night
Entire guest suite in Annapolis
Annapolis Guest Suite, dogs allowed
2 guestsStudio2 beds1 bath
Free parkingWifiAir conditioning
$52 per night
PLUS
Entire apartment in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
4 guests1 bedroom2 beds1 bath
Free parkingWifiKitchenAir conditioning
$104 per night
SUPERHOST
Private room in Annapolis
Peaceful Workation in Tidy Homestay near USNA
1 guest1 bedroom1 bed2.5 shared baths
Free parkingWifiKitchenAir conditioning
$37 per night
SUPERHOST
Entire apartment in Annapolis
Private Annapolis Inlaw Apartment
4 guests1 bedroom1 bed1 bath
Free parkingWifiKitchenAir conditioning
$90 per night
SUPERHOST
Private room in Annapolis
Chesapeake Mornings
2 guests1 bedroom1 bed1.5 baths
Free parkingWifiKitchenAir conditioning
$51 per night
SUPERHOST
Entire guest suite in Annapolis
right downtown garden oasis (dog-friendly)
2 guests1 bedroom2 beds1 bath
WifiKitchenAir conditioning
$125 per night
SUPERHOST
Entire cottage in Annapolis
Mill Creek Cottage
4 guests2 bedrooms2 beds1 bath
Free parkingWifiKitchenAir conditioning
$145 per night
SUPERHOST
Entire guesthouse in Annapolis
Calico Cottage Guest House
2 guests1 bedroom1 bed1 bath
Free parkingWifiKitchenAir conditioning
$106 per night
PLUS
Entire loft in Annapolis
Step Out to Main Street From a Chic Loft
4 guests1 bedroom1 bed1 bath
WifiKitchenAir conditioning
$158 per night
SUPERHOST
Entire apartment in Annapolis
Modern Apartment over the Heart of Main Street!
6 guests2 bedrooms2 beds1 bath
WifiAir conditioning
$112 per night
SUPERHOST
Entire guesthouse in Annapolis
The Cape Cottage
2 guestsStudio1 bed1 bath
Free parkingWifiAir conditioning
$110 per night
SUPERHOST
Entire house in Annapolis
As mentioned in the Washington Post
6 guests2 bedrooms2 beds1.5 baths
WifiKitchenAir conditioning
$170 per night
SUPERHOST
Private room in Annapolis
Howard's Cove Retreat
2 guests1 bedroom2 beds1 private bath
Free parkingWifiAir conditioning
$75 per night
SUPERHOST
Entire house in Crownsville
The Kayak House
4 guests1 bedroom2 beds1 bath
Free parkingWifiKitchenAir conditioning
$124 per night
SUPERHOST
Private room in Arnold
Detached bedroom, private entrance, en-suite bath!
2 guests1 bedroom1 bed1 private bath
Free parkingWifiKitchenAir conditioning
$72 per night
PLUS
Entire house in Annapolis
Renovated Annapolis Row House a Minute's Walk to USNA
6 guests2 bedrooms3 beds2.5 baths
WifiKitchenAir conditioning
$243 per night
Entire apartment in Annapolis
Downtown Gem in Historic Annapolis
4 guests1 bedroom1 bed1 bath
Free parkingWifiKitchenAir conditioning
$166 per night
Private room in Annapolis
#101 Cozy Private Room in Annapolis
2 guests1 bedroom2 beds1 shared bath
Free parkingWifiKitchenAir conditioning
$34 per night
1 20 of 300+ places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.