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Search results; Over 1,000 homes in Annapolis

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
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds
10–15 Sept
5.0 out of 5 average rating, 147 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
4–9 Oct
4.89 out of 5 average rating, 371 reviews
Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds
10–15 Sept
5.0 out of 5 average rating, 52 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
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
Guest suite in Annapolis
Annapolis Home 5 miles from Downtown Annapolis
4 bedrooms, 4 beds
13–18 Sept
New place to stay
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed
17–22 Oct
5.0 out of 5 average rating, 226 reviews
Top guest favourite
Home in Annapolis
Southgate Sanctuary - Downtown Annapolis
3 bedrooms, 3 beds
17–22 Sept
4.97 out of 5 average rating, 33 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
3BR/2BA Annapolis Cottage
3 bedrooms, 4 beds
10–15 Sept
4.98 out of 5 average rating, 227 reviews
Top guest favourite
Home in Annapolis
4BR Walk to USNA & Dock · Parking
4 bedrooms, 4 beds
11–16 Sept
5.0 out of 5 average rating, 18 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
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds
1–6 Nov
4.92 out of 5 average rating, 1137 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
Top guest favourite
Apartment in Annapolis
Funky Uptown Apt meets Downtown - Hist District
2 bedrooms, 2 double beds
10–15 Sept
4.96 out of 5 average rating, 127 reviews
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds
13–18 Sept
4.93 out of 5 average rating, 15 reviews