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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Charming City Oasis. Walk to harbor, eateries.USNA
4 bedrooms, 4 beds, 2 private bathrooms
8–13 Sept
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4.87 out of 5 average rating, 116 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
30 Jul – 4 Aug
4.92 out of 5 average rating, 78 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, 463 reviews
Superhost
Home in Annapolis
Tide & Tallow - Walk to Downtown, Main St, Academy
3 bedrooms, 3 beds
19–24 Jul
4.74 out of 5 average rating, 35 reviews
Top guest favourite
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
1 bed
19–24 Jul
5.0 out of 5 average rating, 172 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
27 Jul – 1 Aug
4.98 out of 5 average rating, 59 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
10–15 Aug
4.93 out of 5 average rating, 183 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
10–15 Aug
4.89 out of 5 average rating, 362 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds
30 Sept – 5 Oct
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Flat in Annapolis
Beautiful Historic Home next to City Dock + USNA
3 bedrooms, 4 beds
10–15 Aug
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed
21–26 Jul
4.96 out of 5 average rating, 130 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds
16–21 Aug
4.97 out of 5 average rating, 94 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed
19–24 Jul
4.96 out of 5 average rating, 223 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
16–21 Aug
4.93 out of 5 average rating, 180 reviews
Superhost
Home in Annapolis
*NEW* Beautiful, Walkable Home Near Town/USNA
3 bedrooms, 4 beds
18–23 Aug
New place to stay
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds
25–30 Jul
4.93 out of 5 average rating, 58 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms
19–24 Jul
4.93 out of 5 average rating, 29 reviews
Top guest favourite
Home in Annapolis
Cute bungalow blocks to Stadium
2 bedrooms, 3 beds
25–30 Jul
4.96 out of 5 average rating, 72 reviews
Top guest favourite
Home in Annapolis
Peaceful Waterfront Home in Annapolis 3BR 2BA.
3 bedrooms, 4 beds
19–24 Aug
4.99 out of 5 average rating, 81 reviews