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Search results; Over 1,000 homes in Annapolis

Guest favourite
Apartment in Annapolis
Annapolis @Gate 1 steps to the Harbor Free parking
1 bedroom, 2 beds, 1 private bathroom
6–11 Sept
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4.91 out of 5 average rating, 150 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, WC
16–21 Sept
4.92 out of 5 average rating, 61 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, 117 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
20–25 Sept
4.95 out of 5 average rating, 189 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
13–18 Sept
4.93 out of 5 average rating, 192 reviews
Top guest favourite
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
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
Nautical Luxe Retreat 6 Guests • 3 BDR • 2 Baths
3 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.96 out of 5 average rating, 150 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
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 470 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, 460 reviews
Top guest favourite
Home in Annapolis
The Red Door Cottage - Pet-Friendly!
2 bedrooms, 2 beds, 2 bathrooms
28 Nov – 3 Dec
5.0 out of 5 average rating, 39 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
13–18 Sept
4.94 out of 5 average rating, 189 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, 1135 reviews
Top guest favourite
Apartment in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 345 reviews
Top guest favourite
Home in Annapolis
Historic Home w/ Parking Steps From Capital & USNA
1 bedroom, 2 beds, 1.5 bathrooms
10–15 Nov
4.98 out of 5 average rating, 104 reviews
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
10–15 Sept
4.97 out of 5 average rating, 65 reviews
Top guest favourite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.94 out of 5 average rating, 422 reviews
Guest favourite
Home in Annapolis
Fleet St Retreat in Downtown - Great Location!
2 bedrooms, 3 beds, 2.5 bathrooms
13–18 Sept
4.91 out of 5 average rating, 123 reviews