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Search results; Over 1,000 homes in Annapolis

Guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 private bathroom
25–30 Oct
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4.96 out of 5 average rating, 240 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
19–24 Jul
4.91 out of 5 average rating, 70 reviews
Guest favourite
Home in Annapolis
Quiet Home Close to Downtown Annapolis and Parks
4 bedrooms, 5 beds
1–6 Nov
4.9 out of 5 average rating, 63 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds
15–20 Aug
5.0 out of 5 average rating, 8 reviews
Superhost
Home in Annapolis
Eastport 3 bedroom Cottage: Walk to Downtown
3 bedrooms, 4 beds
1–6 Jul
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds
5–10 Jul
4.92 out of 5 average rating, 88 reviews
Top guest favourite
Flat in Annapolis
The Sail Loft
3 bedrooms, 4 beds
25–30 Jul
5.0 out of 5 average rating, 33 reviews
Guest favourite
Home in Annapolis
1 Block to USNA Stadium: Modern Annapolis Home!
2 bedrooms, 3 beds
5–10 Jul
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Annapolis
Charming on Charles Street
3 bedrooms, 4 beds
5–10 Jul
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Annapolis
West street historic home
5 bedrooms, 6 beds
1–6 Jul
4.98 out of 5 average rating, 65 reviews
Guest favourite
Home in Arnold
Rachel's BnB
2 bedrooms, 3 beds
5–10 Jul
4.9 out of 5 average rating, 131 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
14–19 Aug
4.97 out of 5 average rating, 461 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
6–11 Jul
4.99 out of 5 average rating, 153 reviews
Guest favourite
Home in Annapolis
Historic 4BR Naptown Home <1 Mile to Stadium
4 bedrooms, 8 beds
13–18 Sept
4.98 out of 5 average rating, 65 reviews
Guest favourite
Home in Annapolis
Cute bungalow blocks to Stadium
2 bedrooms, 3 beds
1–6 Jul
4.96 out of 5 average rating, 70 reviews
Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds
1–6 Jul
4.96 out of 5 average rating, 255 reviews
Top guest favourite
Home in Annapolis
Quaint in the Heart of Annapolis
2 bedrooms, 2 double beds
24–29 Jul
5.0 out of 5 average rating, 113 reviews
Top guest favourite
Apartment in Annapolis
Cozy Annapolis Condo
2 bedrooms, 3 beds
7–12 Jul
4.97 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
12–17 Jul
5.0 out of 5 average rating, 8 reviews