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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
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, 11 reviews
Top guest favourite
Home in Annapolis
Quiet Waterfront
3 bedrooms, 3 beds
26–31 Jul
4.98 out of 5 average rating, 188 reviews
Top guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
3 bedrooms, 6 beds
19–24 Jul
4.92 out of 5 average rating, 132 reviews
Top guest favourite
Flat in Annapolis
The Sail Loft
3 bedrooms, 4 beds
25–30 Jul
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Home in Annapolis
Fenced + Fire Pit + Coffee Bar 2 miles from USNA
4 bedrooms, 4 beds
10–15 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds
13–18 Sept
4.92 out of 5 average rating, 89 reviews
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds
21–26 Jul
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
30 Jul – 4 Aug
4.92 out of 5 average rating, 76 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms
13–18 Jul
4.93 out of 5 average rating, 28 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
24–29 Aug
4.97 out of 5 average rating, 463 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
19–24 Jul
4.98 out of 5 average rating, 58 reviews
Top guest favourite
Home in Annapolis
Marymont Cottage
3 bedrooms, 3 beds
30 Jul – 4 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Edgewater
3 BRs House+Patio+Playground
3 bedrooms, 3 beds
2–7 Aug
4.92 out of 5 average rating, 93 reviews
Top guest favourite
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
4 bedrooms, 4 beds
13–18 Jul
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds
13–18 Jul
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Annapolis
West street historic home
5 bedrooms, 6 beds
19–24 Jul
4.99 out of 5 average rating, 68 reviews
Guest favourite
Apartment in Annapolis
Semper Fi Condo
2 bedrooms, 3 queen beds
2–7 Aug
5.0 out of 5 average rating, 12 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, 66 reviews