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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Apartment in Annapolis
1 bedroom -king in Annapolis- low cleaning fee
1 bedroom, 3 beds, 1 private bathroom
18–23 Jul
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4.97 out of 5 average rating, 125 reviews
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
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
4.93 out of 5 average rating, 179 reviews, 1 queen bed, 1.5 bathrooms
1–6 Aug
Top guest favourite
Home in Annapolis
CJ's Cottage
4.96 out of 5 average rating, 73 reviews, 2 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
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
Guest favourite
Apartment in Annapolis
Semper Fi Condo
5.0 out of 5 average rating, 13 reviews, 2 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 6 beds, 3 bathrooms
12–17 Sept
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
4.92 out of 5 average rating, 1123 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
4.86 out of 5 average rating, 72 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
19–24 Jul
Top guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
5.0 out of 5 average rating, 22 reviews, 4 bedrooms, 6 beds, 2.5 bathrooms
23–28 Jul
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment
4.91 out of 5 average rating, 106 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, 355 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
4.93 out of 5 average rating, 182 reviews, 1 queen bed, 1.5 bathrooms
24–29 Jul
Guest favourite
Flat in Annapolis
Crow’s Nest Cottage - Down Under: Chesapeake Bay
4.95 out of 5 average rating, 22 reviews, 3 bedrooms, 7 beds, 1 bathroom
26–31 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
Flat in Annapolis
Private Annapolis Inlaw Apartment
4.89 out of 5 average rating, 361 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
4.95 out of 5 average rating, 22 reviews, 2 bedrooms, 6 beds, 2 bathrooms
21–26 Jul
Top guest favourite
Flat in Annapolis
Beautiful Historic Home next to City Dock + USNA
5.0 out of 5 average rating, 52 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
10–15 Aug
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
4.93 out of 5 average rating, 28 reviews, 3 bedrooms, 2 bathrooms
19–24 Jul