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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
30 Aug – 4 Sept
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4.97 out of 5 average rating, 469 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
13–18 Sept
4.94 out of 5 average rating, 187 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
23–28 Aug
4.93 out of 5 average rating, 85 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds
21–26 Aug
4.92 out of 5 average rating, 1132 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 18 reviews
Room in Bowie
Cozy Private Queen Room | Free Parking | Near DC
1 queen bed
17–22 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed
13–18 Aug
4.9 out of 5 average rating, 49 reviews
Guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
4 bedrooms, 6 beds
15–20 Aug
4.92 out of 5 average rating, 25 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, 186 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed
13–18 Aug
4.96 out of 5 average rating, 225 reviews
Guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds
23–28 Aug
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Guest house in Stevensville
Private Guesthouse | 7-acres | Near wedding venues
2 bedrooms, 3 beds
13–18 Aug
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds
29 Oct – 3 Nov
5.0 out of 5 average rating, 32 reviews
Guest favourite
Home in Annapolis
Pet-Friendly Annapolis Getaway | USNA & Beach/Bay
3 bedrooms, 5 beds
21–26 Aug
4.91 out of 5 average rating, 23 reviews
Guest favourite
Flat in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
1 bedroom, 3 beds
16–21 Aug
4.92 out of 5 average rating, 520 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
6–11 Sept
4.98 out of 5 average rating, 63 reviews
Top guest favourite
Room in Severna Park
Severna Park Private Entry Suite
2 beds
19–24 Aug
4.98 out of 5 average rating, 63 reviews
Top guest favourite
Home in Annapolis
Large Priv. Suite Near D-town Annapolis & Stadium
1 bedroom, 1 queen bed
13–18 Aug
4.97 out of 5 average rating, 32 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, 190 reviews