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Search results; Over 1,000 homes in Annapolis

Guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 private bathroom
25–30 Oct
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4.96 out of 5 average rating, 240 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
19–24 Jul
4.91 out of 5 average rating, 70 reviews
Top guest favourite
Room in Annapolis
Lovely Private Master Bedroom
1 queen bed
1–6 Jul
4.98 out of 5 average rating, 245 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
26–31 Jul
4.95 out of 5 average rating, 180 reviews
Place to stay in Annapolis
Brand new computer cybersecurity cleaning fee $200
1 bed
1–6 Jul
New place to stay
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds
12–17 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds
1–6 Jul
4.96 out of 5 average rating, 255 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds
13–18 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
6–11 Jul
4.98 out of 5 average rating, 57 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
14–19 Aug
4.97 out of 5 average rating, 461 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
24–29 Jul
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
1 bed
6–11 Jul
5.0 out of 5 average rating, 170 reviews
Top guest favourite
Guest suite in Arnold
Coastal Comfort Retreat near Annapolis, EV charger
1 bedroom, 2 beds
1–6 Jul
4.94 out of 5 average rating, 214 reviews
Guest suite in Arnold
Pool Retreat Near Annapolis & Naval Academy
2 bedrooms, 3 beds
5–10 Jul
4.87 out of 5 average rating, 123 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
27 Jul – 1 Aug
4.89 out of 5 average rating, 358 reviews
Guest favourite
Home in Annapolis
1 Block to USNA Stadium: Modern Annapolis Home!
2 bedrooms, 3 beds
5–10 Jul
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Annapolis
Pet-Friendly Annapolis Stay | Near USNA and Beach
3 bedrooms, 5 beds
5–10 Jul
4.9 out of 5 average rating, 20 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed
16–21 Aug
4.9 out of 5 average rating, 352 reviews
Hotel room in Annapolis
Historic Inn Stay | Steps from Maryland State
1 bedroom, 1 double bed
1–6 Jul
New place to stay