filters

Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 beds, 1 private bathroom
3–8 Oct
,
4.97 out of 5 average rating, 471 reviews
Top guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds
20–25 Sept
5.0 out of 5 average rating, 147 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
Guest favourite
Home in Annapolis
Beautiful house in the best location!
3 bedrooms, 6 beds
21–26 Sept
4.94 out of 5 average rating, 54 reviews
Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds
13–18 Sept
5.0 out of 5 average rating, 52 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, 177 reviews
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
Top guest favourite
Apartment in Annapolis
Funky Uptown Apt meets Downtown - Hist District
2 bedrooms, 2 double beds
28 Sept – 3 Oct
4.96 out of 5 average rating, 127 reviews
Top guest favourite
Home in Annapolis
Southgate Sanctuary - Downtown Annapolis
3 bedrooms, 3 beds
20–25 Sept
4.97 out of 5 average rating, 33 reviews
Flat in Annapolis
Chic 2BR + Den | Annapolis | Sleeps 6
3 bedrooms, 2 beds
14–19 Sept
New place to stay
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
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
Home in Annapolis
3BR/2BA Annapolis Cottage
3 bedrooms, 4 beds
20–25 Sept
4.98 out of 5 average rating, 227 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
Home in Annapolis
Peaceful Waterfront Home in Annapolis 3BR 2BA.
3 bedrooms, 4 beds
28 Sept – 4 Oct
4.99 out of 5 average rating, 89 reviews
Top guest favourite
Townhouse in Annapolis
Beautiful Downtown Annapolis Townhome!
3 bedrooms, 7 beds
13–18 Sept
5.0 out of 5 average rating, 119 reviews
Top guest favourite
Cottage in Annapolis
Charming City Retreat. Walk-harbor, eateries.USNA
4 bedrooms, 4 beds
28 Sept – 3 Oct
4.87 out of 5 average rating, 118 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
Gorgeous Historic Downtown Annapolis House
5 bedrooms, 9 beds
11–16 Oct
4.98 out of 5 average rating, 160 reviews