Search results; Over 1,000 places in Annapolis

Display total before taxes

The home you selected

Guest favorite
Home in Annapolis
Eastport Haven House
9 guests4 bedrooms6 beds4 baths
Apr 20 – 25
More
Apr 20 – 25
More
G$90,224 GYD per night

Explore more homes

Top guest favorite
Room in Annapolis
Stay with Michael
Osprey Room - Charming private room, Annapolis
Jun 11 – 16
G$15,229 GYD per night
4.91 out of 5 average rating, 125 reviews
Guest favorite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 queen bed
Apr 19 – 24
G$24,448 GYD per night
4.91 out of 5 average rating, 1010 reviews
Top guest favorite
Room in Annapolis
Stay with Michael
Blue Heron Room - Charming Private Room, Annapolis
Apr 20 – 25
G$13,888 GYD per night
4.98 out of 5 average rating, 127 reviews
Home in Annapolis
Annapolis/USNA Retreat | Waterfront Community
Free cancellation
Apr 15 – 20
G$37,103 GYD per night
New place to stay
Guest favorite
Guesthouse in Annapolis
Calico Cottage Guest House, king bed, free parking
Free cancellation
Apr 20 – 25
G$21,719 GYD per night
4.89 out of 5 average rating, 275 reviews
Guest favorite
Apartment in Annapolis
Modern Apartment over the Heart of Main Street!
2 queen beds
Apr 18 – 23
G$23,586 GYD per night
4.82 out of 5 average rating, 756 reviews
Guest favorite
Home in Annapolis
Historic Downtown in-law suite
Free cancellation
Oct 27 – Nov 1
G$33,280 GYD per night
4.96 out of 5 average rating, 167 reviews
Top guest favorite
Room in Annapolis
Stay with JenniferHosting for 7 years,
Chesapeake Mornings
May 9 – 14
G$17,958 GYD per night
4.96 out of 5 average rating, 540 reviews
Top guest favorite
Apartment in Annapolis
Beautiful Historic Home next to City Dock + USNA
4 beds
Apr 20 – 25
G$44,261 GYD per night
5.0 out of 5 average rating, 13 reviews
Top guest favorite
Condo in Annapolis
1st Floor Condo in Annapolis
Free cancellation
Apr 26 – May 1
G$38,082 GYD per night
4.95 out of 5 average rating, 44 reviews
Apartment in Annapolis
Naptown's Nauti Flat
2 queen beds
May 4 – 9
G$38,297 GYD per night
New place to stay
Top guest favorite
Condo in Annapolis
Welcome to Annapolis-very low cleaning fee
Free cancellation
Apr 20 – 25
G$41,002 GYD per night
4.97 out of 5 average rating, 96 reviews
Guest favorite
Apartment in Annapolis
Annapolis Escape @Gate 1 and Harbor Free parking
2 beds
Apr 13 – 18
G$25,285 GYD per night
4.86 out of 5 average rating, 51 reviews
Top guest favorite
Condo in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
Free cancellation
Jun 28 – Jul 3
G$60,862 GYD per night
4.96 out of 5 average rating, 268 reviews
Guest favorite
Apartment in Annapolis
King George Hideaway
1 sofa bed
Apr 13 – 18
G$41,540 GYD per night
4.92 out of 5 average rating, 97 reviews
Top guest favorite
Room in Annapolis
Stay with Michael
Sandpiper Room - Charming private room, Annapolis
May 26 – 31
G$14,654 GYD per night
4.93 out of 5 average rating, 129 reviews
Top guest favorite
Guesthouse in Stevensville
Waterfront Getaway - View of bay from your bed
Free cancellation
May 4 – 9
G$47,946 GYD per night
4.99 out of 5 average rating, 266 reviews
Superhost
Apartment in Annapolis
Charming Eastport
Free cancellation
Apr 20 – 25
G$28,998 GYD per night
4.76 out of 5 average rating, 255 reviews