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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Guest house in Annapolis
Garden View, a spacious 1 bedroom with loft.
2 bedrooms, 3 beds, 1 private bathroom
30 Jul – 4 Aug
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4.99 out of 5 average rating, 160 reviews
Top guest favourite
Flat in Annapolis
Perfect Eastport location
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
4.98 out of 5 average rating, 142 reviews
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds, 1 bathroom
9–14 Nov
4.97 out of 5 average rating, 454 reviews
Top guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed, 1 bathroom
6–11 Jul
4.96 out of 5 average rating, 127 reviews
Top guest favourite
Home in Annapolis
Downtown Home/ Central Location
2 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds, 2 bathrooms
1–6 Jul
4.96 out of 5 average rating, 255 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
24–29 Jul
4.93 out of 5 average rating, 179 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
26–31 Jul
4.95 out of 5 average rating, 180 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
9–14 Jul
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
2 bedrooms, 4 beds, 1.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Guest suite in Annapolis
Restful guest suite, scent-free, step-free
3 bedrooms, 3 queen beds, 1 bathroom
7–12 Jul
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Home in Annapolis
Marymont Cottage
3 bedrooms, 3 beds, 2 bathrooms
6–11 Jul
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Apartment in Annapolis
Cozy Annapolis Condo
2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
4.97 out of 5 average rating, 72 reviews
Top guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
4.94 out of 5 average rating, 200 reviews
Guest favourite
Flat in Annapolis
Annapolis 4 Steps to Harbor Backs to Gate 1
1 bedroom, 2 beds, 1 bathroom
5–10 Jul
4.96 out of 5 average rating, 27 reviews
Guest favourite
Flat in Annapolis
King George Downtown Annapolis Getaway
2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
4.86 out of 5 average rating, 122 reviews
Guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
4.96 out of 5 average rating, 240 reviews
Guest favourite
Home in Annapolis
Cozy Cottage
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
4.96 out of 5 average rating, 25 reviews
Townhouse in Annapolis
Townhouse - 1 Mile from Downtown Strip
3 bedrooms, 4 beds, 3 bathrooms
6–11 Jul
4.92 out of 5 average rating, 245 reviews