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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Cape St. Claire
Beach Access, Hot Tub, Pet Friendly, Fully Fenced
4 bedrooms, 4 beds, 2.5 private bathrooms
13–18 Sept
,
4.99 out of 5 average rating, 139 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
4.92 out of 5 average rating, 1123 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Flat in Annapolis
Perfect Eastport location
4.98 out of 5 average rating, 144 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Boat in Annapolis
Welcome Aboard!
4.96 out of 5 average rating, 111 reviews, 2 bedrooms, 3 beds, 2 bathrooms
29 Jul – 3 Aug
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
4.93 out of 5 average rating, 179 reviews, 1 queen bed, 1.5 bathrooms
1–6 Aug
Top guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
4.96 out of 5 average rating, 245 reviews, 1 bedroom, 2 beds, 1 bathroom
25–30 Oct
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
4.97 out of 5 average rating, 463 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Aug
Top guest favourite
Home in Annapolis
Historic Home w/ Parking Steps From Capital & USNA
4.98 out of 5 average rating, 96 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
23–28 Aug
Top guest favourite
Home in Annapolis
Peaceful Waterfront Home in Annapolis 3BR 2BA.
4.99 out of 5 average rating, 80 reviews, 3 bedrooms, 4 beds, 2 bathrooms
24–29 Jul
Top guest favourite
Home in Annapolis
Updated Eastport Gem with Outdoor Fireplace!!
5.0 out of 5 average rating, 58 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
14–19 Jul
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 76 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
30 Jul – 4 Aug
Top guest favourite
Home in Annapolis
Gorgeous Historic Downtown Annapolis House
4.98 out of 5 average rating, 156 reviews, 5 bedrooms, 9 beds, 3.5 bathrooms
13–18 Jul
Top guest favourite
Apartment in Annapolis
Cozy Annapolis Condo
4.97 out of 5 average rating, 73 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4.97 out of 5 average rating, 39 reviews, 4 bedrooms, 6 beds, 3.5 bathrooms
21–26 Jul
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
4.97 out of 5 average rating, 93 reviews, 2 beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
13–18 Jul
Superhost
Home in Annapolis
The Naval Nook 1.3 mi. from Downtown Annapolis
4.9 out of 5 average rating, 170 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Jul
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
4.97 out of 5 average rating, 455 reviews, 1 bedroom, 2 beds, 1 bathroom
29 Nov – 4 Dec