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
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
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
1 queen bed
30 Jul – 4 Aug
4.92 out of 5 average rating, 76 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, 1124 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
Guest favourite
Room in Annapolis
Stay with Michael
Sandpiper Room - Charming private room, Annapolis
24–29 Jul
4.93 out of 5 average rating, 183 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
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
Guest suite in Annapolis
Bay View Studio Apartment
2 beds
16–21 Aug
4.97 out of 5 average rating, 93 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment
1 bed
16–21 Aug
4.91 out of 5 average rating, 106 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
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
5 beds
9–14 Aug
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
27 Jul – 1 Aug
4.98 out of 5 average rating, 58 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
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
4 beds
19–24 Jul
4.86 out of 5 average rating, 72 reviews
Guest favourite
Apartment in Annapolis
Semper Fi Condo
3 queen beds
2–7 Aug
5.0 out of 5 average rating, 13 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
Home in Annapolis
Cozy Stay in Downtown Naptown
19–24 Jul
4.93 out of 5 average rating, 28 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