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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds, 2 private bathrooms
26–31 Oct
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4.97 out of 5 average rating, 115 reviews
Top guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds
9–14 Sept
5.0 out of 5 average rating, 147 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 174 reviews
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
20–25 Sept
4.97 out of 5 average rating, 66 reviews
Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds
9–14 Sept
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
3–8 Oct
4.97 out of 5 average rating, 470 reviews
Top guest favourite
Home in Annapolis
3BR/2BA Annapolis Cottage
3 bedrooms, 4 beds
9–14 Sept
4.98 out of 5 average rating, 226 reviews
Top guest favourite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2 bedrooms, 2 beds
26 Sept – 1 Oct
4.94 out of 5 average rating, 426 reviews
Top guest favourite
Home in Annapolis
Elegant & Authentic Annapolis
1 bedroom, 1 queen bed
20–25 Sept
4.99 out of 5 average rating, 158 reviews
Top guest favourite
Home in Annapolis
The Red Door Cottage - Pet-Friendly!
2 bedrooms, 2 beds
29 Nov – 4 Dec
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Home in Annapolis
Southgate Sanctuary - Downtown Annapolis
3 bedrooms, 3 beds
16–21 Sept
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Apartment in Annapolis
Funky Uptown Apt meets Downtown - Hist District
2 bedrooms, 2 double beds
9–14 Sept
4.96 out of 5 average rating, 126 reviews
Top guest favourite
Flat in Annapolis
Perfect Eastport location
2 bedrooms, 3 beds
13–18 Sept
4.98 out of 5 average rating, 147 reviews
Top guest favourite
Cottage in Annapolis
Charming Cottage 2 parking spot easy walk downtown
2 bedrooms, 3 beds
1–6 Nov
4.94 out of 5 average rating, 214 reviews
Top guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
3 bedrooms, 3 beds
21–26 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Place to stay in Annapolis
Guest Suite Getaway near Naval Academy Stadium
1 bed
9–14 Sept
5.0 out of 5 average rating, 175 reviews
Guest favourite
Flat in Annapolis
King George Downtown Annapolis Getaway
2 bedrooms, 2 beds
13–18 Sept
4.85 out of 5 average rating, 128 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds
20–25 Sept
4.91 out of 5 average rating, 92 reviews
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds
3–8 Dec
4.97 out of 5 average rating, 462 reviews