Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 private bathroom
25–30 Oct
,
4.97 out of 5 average rating, 237 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
28 Jun – 3 Jul
4.95 out of 5 average rating, 177 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
28 Jun – 3 Jul
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment
1 bedroom1 bed,
28 Jun – 3 Jul
4.91 out of 5 average rating, 97 reviews
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom1 bed,
13–18 Jul
5.0 out of 5 average rating, 209 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
9–14 Jul
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Home in Annapolis
Villa Annapolitana • Parking 1 min • USNA 4 min
3 bedrooms3 beds,
9–14 Jul
4.97 out of 5 average rating, 143 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
27 Jun – 2 Jul
4.99 out of 5 average rating, 151 reviews
Top guest favourite
Home in Annapolis
Marymont Cottage
3 bedrooms3 beds,
6–11 Jul
5.0 out of 5 average rating, 26 reviews
Guest favourite
Flat in Annapolis
King George Hideaway
1 bedroom1 sofa bed,
5–10 Jul
4.92 out of 5 average rating, 116 reviews
Guest favourite
Home in Annapolis
Beautiful house in the best location!
3 bedrooms6 beds,
30 Aug – 4 Sept
4.95 out of 5 average rating, 43 reviews
Guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms
5–10 Jul
4.91 out of 5 average rating, 23 reviews
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms6 beds,
22–27 Jul
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Apartment in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
1 bedroom2 beds,
7–12 Jul
4.96 out of 5 average rating, 337 reviews
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms5 beds,
26 Jun – 1 Jul
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Annapolis
Bungalow Basement in Annapolis
1 bedroom4 beds,
15–20 Jun
4.9 out of 5 average rating, 50 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom2 beds,
4–9 Jul
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Annapolis
Historic Home w/ Parking Steps From Capital & USNA
1 bedroom2 beds,
26–31 Jul
4.98 out of 5 average rating, 93 reviews
Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms3 single beds,
15–20 Jun
5.0 out of 5 average rating, 45 reviews