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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
31 Jul – 5 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
5–10 Jul
4.98 out of 5 average rating, 142 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
6–11 Jul
4.98 out of 5 average rating, 57 reviews
Top guest favourite
Home in Annapolis
Downtown Home/ Central Location
2 bedrooms, 6 beds
5–10 Jul
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
2 bedrooms, 4 beds
13–18 Jul
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Home in Annapolis
Marymont Cottage
3 bedrooms, 3 beds
6–11 Jul
5.0 out of 5 average rating, 28 reviews
Guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds
25–30 Oct
4.96 out of 5 average rating, 240 reviews
Guest favourite
Home in Annapolis
Cozy Cottage
2 bedrooms, 3 beds
5–10 Jul
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
3 bedrooms, 4 beds
5–10 Jul
4.94 out of 5 average rating, 200 reviews
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds
30 Jul – 4 Aug
4.96 out of 5 average rating, 110 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds
5–10 Jul
4.92 out of 5 average rating, 89 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
27 Jul – 1 Aug
4.89 out of 5 average rating, 358 reviews
Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds
10–15 Jul
4.97 out of 5 average rating, 35 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
9–14 Jul
4.93 out of 5 average rating, 179 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
24–29 Jul
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, 144 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, 461 reviews
Top guest favourite
Home in Annapolis
Charming on Charles Street
3 bedrooms, 4 beds
5–10 Jul
5.0 out of 5 average rating, 27 reviews
Townhouse in Annapolis
Townhouse - 1 Mile from Downtown Strip
3 bedrooms, 4 beds
6–11 Jul
4.92 out of 5 average rating, 244 reviews