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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Apartment in Annapolis
Cozy Annapolis Condo
2 bedrooms, 3 beds, 1 private bathroom
28 Jul – 2 Aug
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4.97 out of 5 average rating, 73 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
4.97 out of 5 average rating, 463 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Aug
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 76 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
30 Jul – 4 Aug
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
5.0 out of 5 average rating, 14 reviews, 4 bedrooms, 6 beds, 3 bathrooms
12–17 Sept
Top guest favourite
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
5.0 out of 5 average rating, 171 reviews, 1 bed, 1 bathroom
13–18 Jul
Guest favourite
Apartment in Annapolis
Semper Fi Condo
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment
4.9 out of 5 average rating, 105 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
4.9 out of 5 average rating, 354 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Home in Annapolis
Severn River Hope Cottage
5.0 out of 5 average rating, 26 reviews, 3 bedrooms, 4 beds, 2 bathrooms
13–18 Jul
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
4.97 out of 5 average rating, 93 reviews, 2 beds, 1 bathroom
16–21 Aug
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
4.93 out of 5 average rating, 181 reviews, 1 queen bed, 1.5 bathrooms
24–29 Jul
Top guest favourite
Home in Annapolis
Historic Charm | Steps from City Dock and the Yard
4.95 out of 5 average rating, 44 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
12–17 Jul
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
4.93 out of 5 average rating, 28 reviews, 3 bedrooms, 2 bathrooms
13–18 Jul
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
4.95 out of 5 average rating, 181 reviews, 1 queen bed, 3 bathrooms
26–31 Jul
Top guest favourite
Guest house in Stevensville
Waterfront-View of Bay from your Bed
4.99 out of 5 average rating, 352 reviews, 1 bed, 1 bathroom
7–12 Sept
Top guest favourite
Home in Annapolis
Stay Retro Naptown
4.95 out of 5 average rating, 80 reviews, 4 bedrooms, 4 beds, 2 bathrooms
24–29 Jul
Guest favourite
Home in Annapolis
Nautical Retreat 6 Guests • 3 BDR • 2 Baths
4.96 out of 5 average rating, 146 reviews, 3 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4.97 out of 5 average rating, 39 reviews, 4 bedrooms, 6 beds, 3.5 bathrooms
21–26 Jul