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Search results; Over 1,000 homes in Annapolis

Guest house in Annapolis
Charming Guest House-Annapolis
1 bedroom, 1 bed, 1 private bathroom
13–18 Sept
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4.81 out of 5 average rating, 31 reviews
Flat in Annapolis
Chic 2BR + Den | Annapolis | Sleeps 6
3 bedrooms, 2 beds
13–18 Sept
New place to stay
Guest favourite
Home in Annapolis
Admiral’s Landing: Walk to Naval Academy, West St.
3 bedrooms, 3 beds
13–18 Sept
4.98 out of 5 average rating, 53 reviews
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed
17–22 Oct
5.0 out of 5 average rating, 226 reviews
Top guest favourite
Guest suite in Annapolis
Cozy Naptown Perch
2 bedrooms, 3 beds
29 Oct – 3 Nov
4.96 out of 5 average rating, 228 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds
20–25 Sept
4.91 out of 5 average rating, 92 reviews
Home in Edgewater
Water's edge retreat ready to relax with you
2 bedrooms, 2 queen beds
1–6 Nov
New place to stay
Top guest favourite
Guest house in Annapolis
Garden View, 1 Bedroom and a Loft.
2 bedrooms, 3 beds
13–18 Sept
4.99 out of 5 average rating, 167 reviews
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds
3–8 Dec
4.97 out of 5 average rating, 462 reviews
Guest favourite
Guest suite in Arnold
Captains Quarters Oasis Near Annapolis, Sleeps 4
1 bedroom, 2 beds
13–18 Sept
4.95 out of 5 average rating, 215 reviews
Superhost
Home in Annapolis
Annapolis Charmer - Perfect Location
3 bedrooms, 3 beds
27 Sept – 2 Oct
New place to stay
Guest favourite
Home in Annapolis
Charming Renovated Historic Home Downtown wParking
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.91 out of 5 average rating, 242 reviews
Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds
12–17 Sept
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Apartment in Annapolis
Funky Uptown Apt meets Downtown - Hist District
2 bedrooms, 2 double beds
28 Sept – 3 Oct
4.96 out of 5 average rating, 127 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds
1–6 Nov
4.92 out of 5 average rating, 1137 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed
25–30 Oct
4.91 out of 5 average rating, 121 reviews
Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds
4–9 Dec
4.96 out of 5 average rating, 263 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
4–9 Oct
4.89 out of 5 average rating, 372 reviews
Flat in Annapolis
Prime Eastport Location-10 Min Walk to City Dock
1 bedroom, 1 queen bed
5–11 Oct
New place to stay