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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 private bathroom
25–30 Oct
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4.97 out of 5 average rating, 238 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
28 Jun – 3 Jul
4.95 out of 5 average rating, 178 reviews
Hotel room in Annapolis
Historic Inn Stay | Steps from Maryland State
1 bedroom, 1 double bed, 1 bathroom
21–26 Jun
New place to stay
Guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment
1 bedroom, 1 bed, 1 bathroom
12–17 Jul
4.9 out of 5 average rating, 99 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
13–18 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed, 1 bathroom
13–18 Jul
5.0 out of 5 average rating, 211 reviews
Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds, 2 bathrooms
24–29 Jun
4.96 out of 5 average rating, 255 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
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, 460 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
26 Jun – 1 Jul
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Guest house in Annapolis
Eastport Gem ~ Walk to Downtown Annapolis
1 bedroom, 2 beds, 1.5 bathrooms
21–26 Jun
5.0 out of 5 average rating, 86 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, 75 reviews
Top guest favourite
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
1 bed, 1 bathroom
22–27 Jun
5.0 out of 5 average rating, 170 reviews
Top guest favourite
Home in Annapolis
Quaint in the Heart of Annapolis
2 bedrooms, 2 double beds, 1 bathroom
29 Jun – 4 Jul
5.0 out of 5 average rating, 111 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
16–21 Aug
4.96 out of 5 average rating, 149 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, 26 reviews
Guest favourite
Home in Arnold
Rachel's BnB
2 bedrooms, 3 beds, 1 bathroom
28 Jun – 3 Jul
4.9 out of 5 average rating, 129 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bathroom
29 Jul – 3 Aug
4.92 out of 5 average rating, 1117 reviews
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds, No bathroom
30 Jun – 5 Jul
4.95 out of 5 average rating, 19 reviews