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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
Studio, 1 bed, 1 private bathroom
26–31 Jul
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4.98 out of 5 average rating, 159 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
30 Jul – 4 Aug
4.92 out of 5 average rating, 78 reviews
Guest favourite
Home in Arnold
Rachel's BnB
2 bedrooms, 3 beds
26–31 Jul
4.91 out of 5 average rating, 137 reviews
Top guest favourite
Guest house in Annapolis
Eastport Gem ~ Walk to Downtown Annapolis
1 bedroom, 2 beds
21–26 Jul
5.0 out of 5 average rating, 93 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed
16–21 Aug
4.9 out of 5 average rating, 355 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
18–23 Jul
4.97 out of 5 average rating, 463 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
10–15 Aug
4.93 out of 5 average rating, 183 reviews
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds
21–26 Jul
4.96 out of 5 average rating, 111 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds
15–20 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
1 bed
16–21 Jul
5.0 out of 5 average rating, 171 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds
19–24 Jul
4.96 out of 5 average rating, 73 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
1–6 Aug
4.93 out of 5 average rating, 179 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
10–15 Aug
4.89 out of 5 average rating, 362 reviews
Superhost
Flat in Annapolis
Walk to Navy Stadium | Private Studio w/ Parking
1 bedroom, 1 queen bed
25–30 Jul
New place to stay
Top guest favourite
Home in Annapolis
Villa Annapolitana • Parking 1 min • USNA 4 min
3 bedrooms, 3 beds
18–23 Jul
4.97 out of 5 average rating, 148 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds
12–17 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed
21–26 Jul
4.96 out of 5 average rating, 130 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed
1–6 Aug
4.91 out of 5 average rating, 106 reviews
Top guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
4 bedrooms, 6 beds
23–28 Jul
5.0 out of 5 average rating, 22 reviews