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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds, 2 private bathrooms
13–18 Sept
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4.96 out of 5 average rating, 83 reviews
Guest favourite
Home in Annapolis
The Corner House-Annapolis
3 bedrooms, 5 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Annapolis
Charming 5BR Naptown Home <1 Mile to Stadium
5 bedrooms, 9 beds, 3.5 bathrooms
11–16 Oct
4.99 out of 5 average rating, 70 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds, 3.5 bathrooms
20–25 Sept
4.91 out of 5 average rating, 92 reviews
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 68 reviews
Top guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 147 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
3–8 Oct
4.97 out of 5 average rating, 471 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
4.93 out of 5 average rating, 15 reviews
Top guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
3 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 24 reviews
Superhost
Home in Annapolis
Oasis by the Bay - Waterfront Heated Pool Hot Tub!
6 bedrooms, 8 beds, 5 bathrooms
20–25 Sept
4.86 out of 5 average rating, 22 reviews
Top guest favourite
Home in Annapolis
3BR/2BA Annapolis Cottage
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.98 out of 5 average rating, 227 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
8–13 Nov
4.94 out of 5 average rating, 191 reviews
Flat in Annapolis
Prime Eastport Location-10 Min Walk to City Dock
1 bedroom, 1 queen bed, 1 bathroom
5–11 Oct
New place to stay
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
25–30 Oct
4.95 out of 5 average rating, 192 reviews
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds, 3.5 bathrooms
4–9 Oct
4.96 out of 5 average rating, 47 reviews
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed, 1 bathroom
9–14 Nov
4.96 out of 5 average rating, 434 reviews
Guest favourite
Home in Annapolis
4BR Family Retreat Near Annapolis w/ Large Yard
4 bedrooms, 6 beds, 2.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 177 reviews