Search results; Over 1,000 homes in Annapolis

Guest favourite
Apartment in Annapolis
Capts Qrtrs - Awesome downtown Annapolis location!
1 bedroom, 1 bed, 1 private bathroom
9–14 Aug
,
4.86 out of 5 average rating, 184 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
1 queen bed
30 Jul – 4 Aug
4.92 out of 5 average rating, 77 reviews
Guest favourite
Room in Annapolis
Stay with Michael
Osprey Room - Charming private room, Annapolis
1–6 Aug
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
2 beds
30 Aug – 4 Sept
4.92 out of 5 average rating, 1125 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 king beds
14–19 Aug
4.97 out of 5 average rating, 463 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
2 beds
11–16 Aug
5.0 out of 5 average rating, 27 reviews
Guest favourite
Home in Arnold
Rachel's BnB
3 beds
26–31 Jul
4.91 out of 5 average rating, 137 reviews
Top guest favourite
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
4 beds
16–21 Jul
5.0 out of 5 average rating, 16 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 king bed
10–15 Aug
4.89 out of 5 average rating, 361 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
3 beds
19–24 Jul
4.96 out of 5 average rating, 73 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
26–31 Jul
4.98 out of 5 average rating, 159 reviews
Top guest favourite
Guest house in Annapolis
Guesthouse on The Weems Creek
1 queen bed
19–24 Jul
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
1 bed
15–20 Jul
5.0 out of 5 average rating, 171 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 king bed
16–21 Aug
4.9 out of 5 average rating, 355 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
6 beds
12–17 Sept
5.0 out of 5 average rating, 16 reviews
Guest favourite
Room in Annapolis
Stay with Michael
Sandpiper Room - Charming private room, Annapolis
10–15 Aug
4.93 out of 5 average rating, 183 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
4 beds
15–20 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
6 beds
23–28 Jul
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 queen bed
15–20 Jul
4.96 out of 5 average rating, 223 reviews