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Search results; Over 1,000 homes in Annapolis

Descriptions are based on details hosts provide
Top guest favourite
Apartment in Annapolis
New Downtown Annapolis Condo With Free Parking
2 bedrooms, 2 beds, 2 private bathrooms
3–10 Oct
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4.98 out of 5 average rating, 165 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
14–19 Aug
4.97 out of 5 average rating, 463 reviews
Guest favourite
Room in Annapolis
1926 Four Square home with fire pit
1 queen bed, 1.5 bathrooms
10–15 Aug
4.93 out of 5 average rating, 183 reviews
Top guest favourite
Loft in Annapolis
Exposed brick loft on Main Street
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.92 out of 5 average rating, 1125 reviews
Superhost
Home in Annapolis
Harbor’s Edge Retreat: Walk to Main St & Academy
3 bedrooms, 3 beds, 1.5 bathrooms
19–24 Jul
4.89 out of 5 average rating, 81 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
1–6 Aug
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Flat in Annapolis
Perfect Eastport location
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
4.98 out of 5 average rating, 144 reviews
Top guest favourite
Room in Annapolis
Cape Cod home with pool and hot tub
1 queen bed, 1 bathroom
17–22 Aug
4.96 out of 5 average rating, 416 reviews
Top guest favourite
Cottage in Annapolis
1910 waterfront cottage with a private dock
1 queen bed, 1 bathroom
26–31 Jul
4.98 out of 5 average rating, 159 reviews
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds, 1 bathroom
29 Nov – 4 Dec
4.97 out of 5 average rating, 455 reviews
Top guest favourite
Guest suite in Annapolis
Fire pit and patio near downtown
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.96 out of 5 average rating, 224 reviews
Guest favourite
Guest house in Annapolis
West Annapolis cottage with a fire pit
1 bedroom, 1 king bed, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 355 reviews
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
2 bedrooms, 4 beds, 1.5 bathrooms
23–28 Jul
4.86 out of 5 average rating, 72 reviews
Top guest favourite
Flat in Annapolis
Screened porch one block from Main St
2 bedrooms, 1 queen bed, 1.5 bathrooms
30 Jul – 4 Aug
4.92 out of 5 average rating, 76 reviews
Top guest favourite
Home in Annapolis
Historic Home w/ Parking Steps From Capital & USNA
1 bedroom, 2 beds, 1.5 bathrooms
23–28 Aug
4.98 out of 5 average rating, 96 reviews
Top guest favourite
Home in Annapolis
Sauna and patio, block from Naval Academy
1 bedroom, 2 beds, 1 bathroom
27 Nov – 2 Dec
4.96 out of 5 average rating, 245 reviews
Top guest favourite
Home in Annapolis
Gorgeous Historic Downtown Annapolis House
5 bedrooms, 9 beds, 3.5 bathrooms
15–20 Jul
4.98 out of 5 average rating, 156 reviews
Top guest favourite
Apartment in Annapolis
Central condo with a pool and balcony
2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
4.97 out of 5 average rating, 73 reviews
Superhost
Flat in Annapolis
1930s craftsman in walkable Eastport
3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.88 out of 5 average rating, 303 reviews