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Search results; Over 1,000 homes in Annapolis

Descriptions are based on details hosts provide
Top guest favourite
Guest house in Annapolis
Carriage House near Navy Stadium, parking, pets
2 bedrooms, 4 beds, 1 private bathroom
26–31 Jul
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4.95 out of 5 average rating, 117 reviews
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
Flat in Annapolis
Screened porch one block from Main St
4.92 out of 5 average rating, 76 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
30 Jul – 4 Aug
Top guest favourite
Loft in Annapolis
Exposed brick loft on Main Street
4.92 out of 5 average rating, 1125 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
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
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 4 bathrooms
16–21 Jul
Guest favourite
Home in Arnold
Rachel's BnB
4.91 out of 5 average rating, 137 reviews, 2 bedrooms, 3 beds, 1 bathroom
26–31 Jul
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
4.98 out of 5 average rating, 159 reviews, 1 bed, 1 bathroom
26–31 Jul
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
4.93 out of 5 average rating, 183 reviews, 1 queen bed, 1.5 bathrooms
10–15 Aug
Top guest favourite
Home in Annapolis
Fire pit and patio near Annapolis
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, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
Superhost
Home in Annapolis
Newly renovated and walkable to City Dock
4.89 out of 5 average rating, 81 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
19–24 Jul
Top guest favourite
Home in Stevensville
Waterfront with swim spa, sauna, and dock
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 6 beds, 3 bathrooms
12–17 Sept
Top guest favourite
Guest house in Annapolis
Art-filled guesthouse with a pool nearby
5.0 out of 5 average rating, 171 reviews, 1 bed, 1 bathroom
15–20 Jul
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
Guest house in Annapolis
West Annapolis cottage with a fire pit
4.9 out of 5 average rating, 355 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
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
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
4.91 out of 5 average rating, 106 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Guest suite in Annapolis
Walk to downtown from a private studio
4.96 out of 5 average rating, 223 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Jul