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Search results; Over 1,000 homes in Annapolis

Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 bed, 1 private bathroom
20–25 Sept
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4.9 out of 5 average rating, 361 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 30 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds
6–11 Aug
4.93 out of 5 average rating, 59 reviews
Guest favourite
Home in Annapolis
The Corner House-Annapolis
3 bedrooms, 5 beds
11–16 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
10–15 Aug
4.89 out of 5 average rating, 367 reviews
Guest favourite
Guest house in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 queen bed
11–16 Aug
4.95 out of 5 average rating, 209 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 469 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
20–25 Sept
4.95 out of 5 average rating, 184 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed
9–14 Aug
4.96 out of 5 average rating, 224 reviews
Top guest favourite
Guest house in Edgewater
1 large room efficiency in detached garage.
1 bedroom, 1 queen bed
12–17 Sept
4.99 out of 5 average rating, 170 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
24–29 Aug
4.98 out of 5 average rating, 62 reviews
Home in Annapolis
DTA - Park and Walk in safe, quiet neighborhood
2 bedrooms, 2 queen beds
9–14 Aug
New place to stay
Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed
9–14 Aug
4.89 out of 5 average rating, 47 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds
30 Sept – 5 Oct
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds
10–15 Aug
4.99 out of 5 average rating, 68 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
16–21 Aug
4.93 out of 5 average rating, 187 reviews
Top guest favourite
Flat in Annapolis
Beautiful Historic Home next to City Dock + USNA
3 bedrooms, 4 beds
14–19 Aug
5.0 out of 5 average rating, 57 reviews
Guest favourite
Home in Annapolis
Peaceful Pet-Friendly Stay | Near USNA and Beaches
3 bedrooms, 5 beds
12–17 Aug
4.91 out of 5 average rating, 23 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
6–11 Sept
4.94 out of 5 average rating, 185 reviews