filters

Search results; Over 1,000 homes in Annapolis

Superhost
Home in Annapolis
Charming Eastport Getaway – Near Downtown & USNA
3 bedrooms, 3 beds, 1.5 private bathrooms
20–25 Sept
,
4.88 out of 5 average rating, 109 reviews
Guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
4.93 out of 5 average rating, 15 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
Admiral’s Landing: Walk to Naval Academy, West St.
3 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 53 reviews
Top guest favourite
Guest suite in Annapolis
Cozy Naptown Perch
2 bedrooms, 3 beds, 1 bathroom
29 Oct – 3 Nov
4.96 out of 5 average rating, 228 reviews
Top guest favourite
Home in Edgewater
3 BRs House+Patio+Playground
3 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
4.93 out of 5 average rating, 105 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
20–25 Sept
4.93 out of 5 average rating, 194 reviews
Top guest favourite
Home in Annapolis
4 bedrooms, 7 beds, 3 bath completely updated
4 bedrooms, 7 beds, 3 bathrooms
11–16 Oct
4.97 out of 5 average rating, 146 reviews
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Annapolis
West street historic home
5 bedrooms, 6 beds, 3 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 73 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed, 1 bathroom
25–30 Oct
4.91 out of 5 average rating, 121 reviews
Top guest favourite
Townhouse in Annapolis
Beautiful Downtown Annapolis Townhome!
3 bedrooms, 7 beds, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 119 reviews
Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 52 reviews
Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
13–18 Sept
New place to stay
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds, 1 bathroom
3–8 Dec
4.97 out of 5 average rating, 462 reviews
Guest favourite
Guest suite in Arnold
Captains Quarters Oasis Near Annapolis, Sleeps 4
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.95 out of 5 average rating, 215 reviews
Top guest favourite
Guest house in Annapolis
Garden View, 1 Bedroom and a Loft.
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 167 reviews
Guest favourite
Home in Annapolis
Beautiful house in the best location!
3 bedrooms, 6 beds, 3.5 bathrooms
13–18 Sept
4.94 out of 5 average rating, 54 reviews
Top guest favourite
Home in Annapolis
Charming on Charles Street
3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 33 reviews