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Search results; Over 1,000 homes in Annapolis

Guest favourite
Townhouse in Annapolis
You'll Never Want to Leave
5 bedrooms, 7 beds, 2.5 private bathrooms
9–14 Jul
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4.85 out of 5 average rating, 143 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
27 Jul – 1 Aug
4.92 out of 5 average rating, 75 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
26–31 Jul
4.99 out of 5 average rating, 157 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
14–19 Aug
4.97 out of 5 average rating, 462 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
19–24 Jul
4.98 out of 5 average rating, 58 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
1–6 Aug
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Home in Annapolis
Nautical Retreat 6 Guests • 3 BDR • 2 Baths
3 bedrooms, 3 beds
22–27 Aug
4.99 out of 5 average rating, 145 reviews
Top guest favourite
Guest house in Annapolis
Guesthouse on The Weems Creek
1 bedroom, 1 queen bed
12–17 Jul
5.0 out of 5 average rating, 44 reviews
Guest favourite
Guest suite in Arnold
Coastal Comfort Retreat near Annapolis, EV charger
1 bedroom, 2 beds
12–17 Jul
4.94 out of 5 average rating, 215 reviews
Guest favourite
Home in Arnold
Rachel's BnB
2 bedrooms, 3 beds
26–31 Jul
4.9 out of 5 average rating, 135 reviews
Top guest favourite
Home in Annapolis
Quaint in the Heart of Annapolis
2 bedrooms, 2 double beds
10–15 Jul
5.0 out of 5 average rating, 113 reviews
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds
13–18 Jul
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds
11–16 Jul
4.96 out of 5 average rating, 72 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment
1 bedroom, 1 bed
12–17 Jul
4.9 out of 5 average rating, 104 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed
8–13 Jul
4.95 out of 5 average rating, 222 reviews
Guest favourite
Apartment in Annapolis
Semper Fi Condo
2 bedrooms, 3 queen beds
2–7 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms
12–17 Jul
4.93 out of 5 average rating, 28 reviews
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
2 bedrooms, 4 beds
19–24 Jul
4.86 out of 5 average rating, 72 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds
12–17 Sept
5.0 out of 5 average rating, 13 reviews