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Search results; Over 1,000 homes in Annapolis

Guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
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
Home in Annapolis
Cozy Stay in Downtown Naptown
4.93 out of 5 average rating, 27 reviews, 3 bedrooms, 2 bathrooms
5–10 Jul
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 73 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
16–21 Jul
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium- Renovated 2BR Downtown
4.86 out of 5 average rating, 72 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
20–25 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
13–18 Sept
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
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
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
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
Guest favourite
Home in Annapolis
Charming Eastport Getaway – Near Downtown & USNA
4.89 out of 5 average rating, 101 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
5–10 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
Superhost
Home in Annapolis
Tide & Tallow - Walk to Downtown, Main St, Academy
4.74 out of 5 average rating, 34 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
5–10 Jul
Top guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
4.92 out of 5 average rating, 131 reviews, 3 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
Guest favourite
Home in Annapolis
Historic 4BR Naptown Home <1 Mile to Stadium
4.98 out of 5 average rating, 66 reviews, 4 bedrooms, 8 beds, 3.5 bathrooms
13–18 Sept
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4.97 out of 5 average rating, 38 reviews, 4 bedrooms, 6 beds, 3.5 bathrooms
23–28 Aug
Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
4.97 out of 5 average rating, 35 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
10–15 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