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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 beds, 1 private bathroom
14–19 Aug
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4.97 out of 5 average rating, 463 reviews
Home in Pasadena
Spacious Family Home in Pasadena
3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Jul
New place to stay
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
23–28 Aug
4.92 out of 5 average rating, 78 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
16–21 Aug
4.93 out of 5 average rating, 181 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
10–15 Aug
4.93 out of 5 average rating, 186 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
5.0 out of 5 average rating, 13 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 355 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bathroom
26–31 Jul
4.98 out of 5 average rating, 161 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, WC
25–30 Jul
4.93 out of 5 average rating, 58 reviews
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds, 2 bathrooms
24–29 Jul
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
26–31 Jul
4.93 out of 5 average rating, 30 reviews
Home in Annapolis
Waterfront Gem w/ Dock: 2 Mi to Dwtn Annapolis!
4 bedrooms, 6 beds, 3 bathrooms
1–6 Aug
New place to stay
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds, 3 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed, 1 bathroom
21–26 Jul
4.96 out of 5 average rating, 224 reviews
Guest favourite
Home in Annapolis
Admiral’s Landing: Walk to Naval Academy, West St.
3 bedrooms, 3 beds, 1.5 bathrooms
26–31 Jul
4.98 out of 5 average rating, 46 reviews
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds, 2.5 bathrooms
26–31 Jul
4.93 out of 5 average rating, 30 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds, 1 bathroom
13–18 Aug
5.0 out of 5 average rating, 28 reviews
Guest favourite
Flat in Annapolis
NEW lovely studio apartment with onsite parking!
1 bedroom, 1 queen bed, 1 bathroom
21–26 Jul
4.85 out of 5 average rating, 125 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
4.96 out of 5 average rating, 74 reviews