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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Cape St. Claire
Beach Access, Hot Tub, Pet Friendly, Fully Fenced
4 bedrooms, 4 beds, 2.5 private bathrooms
13–18 Sept
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4.99 out of 5 average rating, 139 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
Home in Annapolis
Eastport Waterman's Cottage
3 bedrooms, 4 beds
27 Jul – 1 Aug
5.0 out of 5 average rating, 10 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
Quiet Waterfront
3 bedrooms, 3 beds
26–31 Jul
4.98 out of 5 average rating, 188 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
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
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
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
Cozy Stay in Downtown Naptown
3 bedrooms
19–24 Jul
4.93 out of 5 average rating, 28 reviews
Top guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
3 bedrooms, 3 beds
26–31 Jul
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds
19–24 Jul
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Annapolis
Charming 5BR Naptown Home <1 Mile to Stadium
5 bedrooms, 9 beds
13–18 Sept
4.99 out of 5 average rating, 67 reviews
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds
19–24 Jul
4.95 out of 5 average rating, 22 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
1–6 Aug
4.93 out of 5 average rating, 179 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, 463 reviews
Top guest favourite
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
4 bedrooms, 4 beds
14–19 Jul
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Annapolis
Charming 4BR, 3BA Steps from the water.
4 bedrooms, 5 beds
14–19 Jul
5.0 out of 5 average rating, 57 reviews