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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, 158 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed, 1 bathroom
27 Jul – 1 Aug
4.89 out of 5 average rating, 358 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
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
6–11 Jul
4.98 out of 5 average rating, 57 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
Home in Annapolis
Marymont Cottage
3 bedrooms, 3 beds, 2 bathrooms
6–11 Jul
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds, 2 bathrooms
30 Jul – 4 Aug
4.96 out of 5 average rating, 110 reviews
Top guest favourite
Home in Annapolis
Peaceful Waterfront Home in Annapolis 3BR 2BA.
3 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
4.99 out of 5 average rating, 78 reviews
Top guest favourite
Apartment in Annapolis
Cozy Annapolis Condo
2 bedrooms, 3 beds, 1 bathroom
20–25 Jul
4.97 out of 5 average rating, 72 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
Apartment in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
1 bedroom, 2 beds, 1 bathroom
7–12 Jul
4.96 out of 5 average rating, 338 reviews
Top guest favourite
Home in Annapolis
Nautical Luxe Retreat 6 Guests • 3 BDR • 2 Baths
3 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
4.99 out of 5 average rating, 144 reviews
Guest favourite
Home in Annapolis
Cozy Cottage
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
4.96 out of 5 average rating, 24 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
Top guest favourite
Home in Annapolis
Charming on Charles Street
3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in Annapolis
DTA Row Home | Walk to City Dock & The Yard
2 bedrooms, 3 beds, 2 bathrooms
11–16 Jul
5.0 out of 5 average rating, 14 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
Top guest favourite
Guest house in Annapolis
Eastport Gem ~ Walk to Downtown Annapolis
1 bedroom, 2 beds, 1.5 bathrooms
10–15 Jul
5.0 out of 5 average rating, 88 reviews