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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Apartment in Annapolis
New Downtown Annapolis Condo With Free Parking
2 bedrooms, 2 beds, 2 private bathrooms
3–10 Oct
,
4.98 out of 5 average rating, 165 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
1–6 Aug
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Flat in Annapolis
Perfect Eastport location
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
4.98 out of 5 average rating, 144 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
19–24 Jul
4.98 out of 5 average rating, 58 reviews
Top guest favourite
Home in Annapolis
Historic Home w/ Parking Steps From Capital & USNA
1 bedroom, 2 beds, 1.5 bathrooms
23–28 Aug
4.98 out of 5 average rating, 96 reviews
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds, 1 bathroom
29 Nov – 4 Dec
4.97 out of 5 average rating, 454 reviews
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds, 2 bathrooms
12–17 Jul
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Home in Annapolis
Gorgeous Historic Downtown Annapolis House
5 bedrooms, 9 beds, 3.5 bathrooms
12–17 Jul
4.98 out of 5 average rating, 155 reviews
Guest favourite
Flat in Annapolis
King George Downtown Annapolis Getaway
2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
4.86 out of 5 average rating, 123 reviews
Superhost
Home in Annapolis
Spacious 5 BR house - 5 Min Walk to N-MC Stadium!
3 bedrooms, 9 beds, 3.5 bathrooms
12–17 Jul
4.85 out of 5 average rating, 27 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
16–21 Aug
4.96 out of 5 average rating, 157 reviews
Top guest favourite
Home in Annapolis
Peaceful Waterfront Home in Annapolis 3BR 2BA.
3 bedrooms, 4 beds, 2 bathrooms
24–29 Jul
4.99 out of 5 average rating, 79 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
24–29 Jul
4.93 out of 5 average rating, 181 reviews
Top guest favourite
Guest house in Annapolis
Walk to City Dock & USNA | Designer Eastport Home
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Home in Annapolis
Updated Eastport Gem with Outdoor Fireplace!!
3 bedrooms, 3 beds, 2.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 58 reviews
Top guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
5.0 out of 5 average rating, 19 reviews
Superhost
Flat in Annapolis
Gybeset Eastport Inn
3 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.88 out of 5 average rating, 303 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bathroom
10–15 Aug
4.92 out of 5 average rating, 1123 reviews
Top guest favourite
Home in Annapolis
Historic Charm | Steps from City Dock and the Yard
2 bedrooms, 4 beds, 2.5 bathrooms
12–17 Jul
4.95 out of 5 average rating, 44 reviews