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Search results; Over 1,000 homes in Annapolis

Guest favourite
Home in Cape St. Claire
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, 224 reviews
Guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds, 3.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 89 reviews
Top guest favourite
Flat in Annapolis
The Sail Loft
3 bedrooms, 4 beds, 2 bathrooms
25–30 Jul
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Home in Annapolis
Quiet Waterfront
3 bedrooms, 3 beds, 3 bathrooms
26–31 Jul
4.98 out of 5 average rating, 188 reviews
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
2 bedrooms, 4 beds, 1.5 bathrooms
19–24 Jul
4.86 out of 5 average rating, 72 reviews
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds, 2.5 bathrooms
12–17 Jul
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Annapolis
Admiral’s Landing: Walk to Naval Academy, West St.
3 bedrooms, 3 beds, 1.5 bathrooms
12–17 Jul
4.98 out of 5 average rating, 43 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
16–21 Jul
4.92 out of 5 average rating, 74 reviews
Guest favourite
Home in Annapolis
Historic 4BR Naptown Home <1 Mile to Stadium
4 bedrooms, 8 beds, 3.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 66 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
12–17 Jul
4.93 out of 5 average rating, 28 reviews
Guest favourite
Townhouse in Annapolis
Townhouse - 1 Mile from Downtown Strip
3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
4.92 out of 5 average rating, 245 reviews
Top guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
3 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
4.92 out of 5 average rating, 131 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, 1122 reviews
Top guest favourite
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
4 bedrooms, 4 beds, 4 bathrooms
9–14 Jul
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Cape St. Claire
Beautiful Annapolis Home Near the Beach
4 bedrooms, 7 beds, 3 bathrooms
26–31 Jul
5.0 out of 5 average rating, 13 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
Fenced + Fire Pit + Coffee Bar 2 miles from USNA
4 bedrooms, 4 beds, 3 bathrooms
10–15 Aug
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Annapolis
Across from stadium - walk to downtown Annapolis!
4 bedrooms, 4 beds, 3 bathrooms
20–25 Jul
4.91 out of 5 average rating, 132 reviews