300+ stays
Stays in Annapolis

More than 16,000 guests have stayed in Annapolis.
On average they rated their stays 4.9 out of 5 stars.
SUPERHOST
Entire condominium (condo) in Annapolis
Downtown Annapolis Condo w/ Free Parking + Coffee
4 guests2 bedrooms2 beds2 baths
Free parkingAir conditioningWifiKitchen
$175 per night
SUPERHOST
Entire condominium (condo) in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
4 guests1 bedroom2 beds1 bath
Free parkingAir conditioningWifiKitchen
$143 per night
Entire guest suite in Annapolis
Great one bedroom apartment in Eastport
2 guests1 bedroom1 bed1 bath
Air conditioningWifiKitchen
$115 per night
PLUS
Entire loft in Annapolis
Step Out to Main Street From a Chic Loft
4 guests1 bedroom1 bed1 bath
Air conditioningWifiKitchen
$136 per night
PLUS
Entire rental unit in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
4 guests1 bedroom2 beds1 bath
Free parkingAir conditioningWifiKitchen
$125 per night
SUPERHOST
Entire rental unit in Annapolis
Modern Apartment over the Heart of Main Street!
6 guests2 bedrooms2 beds1 bath
Air conditioningWifi
$140 per night
SUPERHOST
Entire rental unit in Annapolis
Heart of Annapolis, Self Check-in. Walk Everywhere
4 guests1 bedroom1 bed1 bath
Air conditioningWifiKitchen
$166 per night
SUPERHOST
Entire rental unit in Annapolis
Private Annapolis Inlaw Apartment
4 guests1 bedroom1 bed1 bath
Free parkingAir conditioningWifiKitchen
$92 per night
PLUS
Entire residential home in Annapolis
Charming Row House in Historic District
6 guests2 bedrooms3 beds1 bath
Air conditioningWifiKitchen
$221 per night
Entire condominium (condo) in Annapolis
The Crow's Nest - Excellent downtown Annapolis Apt
4 guests1 bedroom2 beds1 bath
Air conditioningWifiKitchen
$161 per night
SUPERHOST
Entire rental unit in Annapolis
Downtown Gem in Historic Annapolis
3 guests1 bedroom1 bed1 bath
Free parkingAir conditioningWifiKitchen
$165 per night
SUPERHOST
Houseboat in Annapolis
Condo Houseboat
4 guests2 bedrooms2 beds2 baths
Free parkingAir conditioningWifiKitchen
$459 per night
SUPERHOST
Entire guest suite in Annapolis
Annapolis Guest Suite, well-behaved pets allowed
2 guestsStudio2 beds1 bath
Free parkingAir conditioningWifi
$56 per night
SUPERHOST
Entire guest suite in Annapolis
Cozy downtown Annapolis studio- walk everywhere!
2 guestsStudio1 bed1 bath
Free parkingAir conditioningWifiKitchen
$142 per night
SUPERHOST
Entire rental unit in Annapolis
Chesapeake Bird Nest
4 guests1 bedroom4 beds1 bath
Free parkingAir conditioningWifiKitchen
$169 per night
SUPERHOST
Entire residential home in Annapolis
As mentioned in the Washington Post
6 guests2 bedrooms2 beds1.5 baths
Air conditioningWifiKitchen
$211 per night
SUPERHOST
Entire residential home in Annapolis
New Hotel Chic
4 guests2 bedrooms2 beds1 bath
Free parkingAir conditioningWifiKitchen
$223 per night
SUPERHOST
Entire rental unit in Annapolis
Brand New Reno in Historic Dist w 2 Parking spots
4 guests2 bedrooms3 beds1 bath
Free parkingAir conditioningWifiKitchen
$169 per night
SUPERHOST
Entire townhouse in Annapolis
Moose’s Happy Place
8 guests3 bedrooms3 beds3.5 baths
Air conditioningWifiKitchen
$400 per night
SUPERHOST
Entire guesthouse in Annapolis
Chesapeake Birdhouse Studio
2 guests1 bedroom1 bed1 bath
Free parkingAir conditioningWifi
$145 per night
1 20 of 300+ places to stay
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