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Search results; Over 1,000 homes in Annapolis

Guest favourite
Home in Annapolis
Country House on the Bay
5 bedrooms, 10 beds, 3 private bathrooms
20–25 Jul
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4.9 out of 5 average rating, 223 reviews
Guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 4 beds, 2 bathrooms
22–27 Jul
Top guest favourite
Home in Annapolis
Quiet Waterfront
4.98 out of 5 average rating, 188 reviews, 3 bedrooms, 3 beds, 3 bathrooms
26–31 Jul
Top guest favourite
Flat in Annapolis
The Sail Loft
5.0 out of 5 average rating, 34 reviews, 3 bedrooms, 4 beds, 2 bathrooms
25–30 Jul
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 72 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
16–21 Jul
Top guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
5.0 out of 5 average rating, 18 reviews, 3 bedrooms, 3 beds, 2 bathrooms
3–8 Jul
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
4.92 out of 5 average rating, 89 reviews, 5 bedrooms, 9 beds, 3.5 bathrooms
5–10 Jul
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
4.97 out of 5 average rating, 461 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Aug
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
4.93 out of 5 average rating, 27 reviews, 3 bedrooms, 2 bathrooms
5–10 Jul
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
4.89 out of 5 average rating, 358 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Top guest favourite
Home in Annapolis
Beautiful house in the best location!
4.96 out of 5 average rating, 46 reviews, 3 bedrooms, 6 beds, 3.5 bathrooms
12–17 Jul
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
5.0 out of 5 average rating, 8 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
12–17 Jul
Guest favourite
Townhouse in Annapolis
Townhouse - 1 Mile from Downtown Strip
4.92 out of 5 average rating, 245 reviews, 3 bedrooms, 4 beds, 3 bathrooms
6–11 Jul
Guest favourite
Home in Arnold
Rachel's BnB
4.9 out of 5 average rating, 134 reviews, 2 bedrooms, 3 beds, 1 bathroom
26–31 Jul
Top guest favourite
Home in Annapolis
Fenced + Fire Pit + Coffee Bar 2 miles from USNA
5.0 out of 5 average rating, 10 reviews, 4 bedrooms, 4 beds, 3 bathrooms
10–15 Aug
Top guest favourite
Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
5.0 out of 5 average rating, 47 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
13–18 Jul
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
4.99 out of 5 average rating, 154 reviews, 1 bed, 1 bathroom
9–14 Jul
Superhost
Home in Annapolis
The Naval Nook 1.3 mi. from Downtown Annapolis
4.9 out of 5 average rating, 168 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
Top guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
4.94 out of 5 average rating, 200 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul