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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, 466 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
16–21 Aug
4.93 out of 5 average rating, 187 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
23–28 Aug
4.95 out of 5 average rating, 184 reviews
Top guest favourite
Room in Annapolis
Cozy Annapolis Retreat – Private Bedroom & Bath
1 queen bed, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 40 reviews
Top guest favourite
Room in Annapolis
Modern Suite with Spa Feel Near Downtown Annapolis
1 king bed, 1 bathroom
10–15 Aug
4.89 out of 5 average rating, 62 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
6–11 Sept
4.94 out of 5 average rating, 185 reviews
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed, 1 bathroom
24–29 Aug
4.96 out of 5 average rating, 421 reviews
Guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
3 bedrooms, 6 beds, 2 bathrooms
22–27 Aug
4.92 out of 5 average rating, 133 reviews
Guest favourite
Apartment in Annapolis
Semper Fi Condo
2 bedrooms, 3 queen beds, 2 bathrooms
17–22 Aug
4.91 out of 5 average rating, 22 reviews
Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.89 out of 5 average rating, 47 reviews
Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 bathroom
27 Nov – 2 Dec
4.96 out of 5 average rating, 251 reviews
Room in Annapolis
Sun-kissed mornings #RM A
1 bed, 1 bathroom
4–9 Aug
4.64 out of 5 average rating, 11 reviews
Top guest favourite
Room in Annapolis
“Room at the Inn…”
1 queen bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.96 out of 5 average rating, 224 reviews
Guest favourite
Room in Annapolis
Quiet-Home Annapolis
1 bed, 2 bathrooms
16–21 Aug
4.85 out of 5 average rating, 105 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
24–29 Aug
4.98 out of 5 average rating, 62 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.92 out of 5 average rating, 1128 reviews
Top guest favourite
Home in Annapolis
Modern Annapolis Getaway - 2 Free Parking Spaces
2 bedrooms, 2 double beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 117 reviews
Guest favourite
Flat in Annapolis
Annapolis 4 Steps to Harbor Backs to Gate 1
1 bedroom, 2 beds, 1 bathroom
10–15 Aug
4.97 out of 5 average rating, 31 reviews