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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, 160 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
16–21 Aug
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 78 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
30 Jul – 4 Aug
Home in Annapolis
Waterfront Gem w/ Dock: 2 Mi to Dwtn Annapolis!
New place to stay, 4 bedrooms, 6 beds, 3 bathrooms
1–6 Aug
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
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
Guest house in Annapolis
Guesthouse on The Weems Creek
5.0 out of 5 average rating, 45 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Jul
Top guest favourite
Boat in Annapolis
Welcome Aboard!
4.96 out of 5 average rating, 111 reviews, 2 bedrooms, 3 beds, 2 bathrooms
21–26 Jul
Top guest favourite
Home in Annapolis
Quaint in the Heart of Annapolis
5.0 out of 5 average rating, 114 reviews, 2 bedrooms, 2 beds, 1 bathroom
24–29 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
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
Stay Retro Naptown
4.95 out of 5 average rating, 80 reviews, 4 bedrooms, 4 beds, 2 bathrooms
24–29 Jul
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
4.95 out of 5 average rating, 182 reviews, 1 queen bed, 3 bathrooms
26–31 Jul
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
4.89 out of 5 average rating, 362 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
4.95 out of 5 average rating, 137 reviews, 2 bedrooms, 3 beds, 1 bathroom
9–15 Sept
Superhost
Flat in Annapolis
Modern Eastport Getaway, Near Historic Annapolis
4.84 out of 5 average rating, 19 reviews, 1 bedroom, 3 beds, 1 bathroom
19–24 Jul
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
17–22 Jul
Top guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
4.96 out of 5 average rating, 130 reviews, 1 queen bed, 1 bathroom
21–26 Jul
Home in Pasadena
Spacious Family Home in Pasadena
New place to stay, 3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Jul