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Search results; Over 1,000 homes in Annapolis

Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
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4.89 out of 5 average rating, 369 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
4.91 out of 5 average rating, 116 reviews
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Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
27 Sept – 2 Oct
4.96 out of 5 average rating, 172 reviews
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds, 1 bathroom
29 Nov – 4 Dec
4.97 out of 5 average rating, 459 reviews
Guest favourite
Home in Riva
Waterfront Annapolis Getaway!
1 bedroom, 1 king bed, 2.5 bathrooms
7–12 Sept
4.92 out of 5 average rating, 97 reviews
Guest favourite
Home in Annapolis
Nautical Retreat 6 Guests • 3 BDR • 2 Baths
3 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.96 out of 5 average rating, 149 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.92 out of 5 average rating, 1133 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 80 reviews
Top guest favourite
Guest house in Stevensville
Waterfront-View of Bay from your Bed
1 queen bed, 1 bathroom
21–26 Sept
4.99 out of 5 average rating, 360 reviews
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 114 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
Home in Annapolis
Gracie's Gallery & Garden in Annapolis
4 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Annapolis
The Red Door Cottage - Pet-Friendly!
2 bedrooms, 2 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 39 reviews
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed, 1 bathroom
17–22 Oct
5.0 out of 5 average rating, 225 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
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed, 1 bathroom
13–18 Sept
4.96 out of 5 average rating, 426 reviews
Top guest favourite
Home in Annapolis
The General's House-Spacious Home w/Pool & Hot Tub
4 bedrooms, 7 beds, 4 bathrooms
22–27 Sept
4.95 out of 5 average rating, 43 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, WC
1–6 Sept
4.92 out of 5 average rating, 61 reviews
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
2 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
4.86 out of 5 average rating, 74 reviews