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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
4.93 out of 5 average rating, 179 reviews, 1 queen bed, 1.5 bathrooms
1–6 Aug
Top guest favourite
Flat in Annapolis
Perfect Eastport location
4.98 out of 5 average rating, 144 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
4.98 out of 5 average rating, 58 reviews, 2 bedrooms, 1.5 bathrooms
19–24 Jul
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
4.97 out of 5 average rating, 454 reviews, 1 bedroom, 2 beds, 1 bathroom
29 Nov – 4 Dec
Top guest favourite
Home in Annapolis
Historic Home w/ Parking Steps From Capital & USNA
4.98 out of 5 average rating, 96 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
23–28 Aug
Top guest favourite
Home in Annapolis
Gorgeous Historic Downtown Annapolis House
4.98 out of 5 average rating, 155 reviews, 5 bedrooms, 9 beds, 3.5 bathrooms
12–17 Jul
Superhost
Home in Annapolis
Spacious 5 BR house - 5 Min Walk to N-MC Stadium!
4.85 out of 5 average rating, 27 reviews, 3 bedrooms, 9 beds, 3.5 bathrooms
12–17 Jul
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
4.95 out of 5 average rating, 22 reviews, 2 bedrooms, 6 beds, 2 bathrooms
12–17 Jul
Guest favourite
Flat in Annapolis
King George Downtown Annapolis Getaway
4.86 out of 5 average rating, 123 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
4.93 out of 5 average rating, 181 reviews, 1 queen bed, 1.5 bathrooms
24–29 Jul
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
4.96 out of 5 average rating, 157 reviews, 2 beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in Annapolis
Peaceful Waterfront Home in Annapolis 3BR 2BA.
4.99 out of 5 average rating, 79 reviews, 3 bedrooms, 4 beds, 2 bathrooms
24–29 Jul
Top guest favourite
Guest house in Annapolis
Walk to City Dock & USNA | Designer Eastport Home
4.98 out of 5 average rating, 42 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Top guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4.97 out of 5 average rating, 39 reviews, 4 bedrooms, 6 beds, 3.5 bathrooms
21–26 Jul
Top guest favourite
Home in Annapolis
Updated Eastport Gem with Outdoor Fireplace!!
5.0 out of 5 average rating, 58 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
13–18 Jul
Superhost
Flat in Annapolis
Gybeset Eastport Inn
4.88 out of 5 average rating, 303 reviews, 3 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
4.96 out of 5 average rating, 415 reviews, 1 queen bed, 1 bathroom
17–22 Aug