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Search results; Over 1,000 homes in Annapolis

Descriptions are based on details hosts provide
Top guest favourite
Cottage in Annapolis
Miller Cottage - near Navy Stadium
1 bedroom, 2 beds, 1 private bathroom
20–25 Jul
,
4.99 out of 5 average rating, 153 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
4.97 out of 5 average rating, 463 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Aug
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
4.93 out of 5 average rating, 183 reviews, 1 queen bed, 1.5 bathrooms
10–15 Aug
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
4.92 out of 5 average rating, 1125 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
Superhost
Home in Annapolis
Harbor’s Edge Retreat: Walk to Main St & Academy
4.89 out of 5 average rating, 81 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
19–24 Jul
Guest favourite
Room in Annapolis
1926 Four Square home near downtown
4.93 out of 5 average rating, 179 reviews, 1 queen bed, 1.5 bathrooms
1–6 Aug
Top guest favourite
Flat in Annapolis
Perfect Eastport location
4.98 out of 5 average rating, 144 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
4.96 out of 5 average rating, 416 reviews, 1 queen bed, 1 bathroom
17–22 Aug
Top guest favourite
Cottage in Annapolis
1910 waterfront cottage with a private dock
4.98 out of 5 average rating, 159 reviews, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Guest suite in Annapolis
Cathedral ceilings in walkable Murray Hill
4.97 out of 5 average rating, 455 reviews, 1 bedroom, 2 beds, 1 bathroom
29 Nov – 4 Dec
Top guest favourite
Guest suite in Annapolis
Fire pit and patio near downtown
4.96 out of 5 average rating, 224 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
4.9 out of 5 average rating, 355 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Superhost
Townhouse in Annapolis
Renovated with a yard, walk to Dock
4.86 out of 5 average rating, 72 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
23–28 Jul
Top guest favourite
Flat in Annapolis
Screened porch one block from Main St
4.92 out of 5 average rating, 76 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
30 Jul – 4 Aug
Top guest favourite
Home in Annapolis
Gorgeous Historic Downtown Annapolis House
4.98 out of 5 average rating, 156 reviews, 5 bedrooms, 9 beds, 3.5 bathrooms
15–20 Jul
Top guest favourite
Apartment in Annapolis
Central condo with a pool and balcony
4.97 out of 5 average rating, 73 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
Top guest favourite
Home in Annapolis
Sauna and patio, block from Naval Academy
4.96 out of 5 average rating, 245 reviews, 1 bedroom, 2 beds, 1 bathroom
27 Nov – 2 Dec
Top guest favourite
Home in Annapolis
Historic Home w/ Parking Steps From Capital & USNA
4.98 out of 5 average rating, 96 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
23–28 Aug
Superhost
Flat in Annapolis
Gybeset Eastport Inn
4.88 out of 5 average rating, 303 reviews, 3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept