filters

Search results; Over 1,000 homes in Annapolis

Photo 1 of 22
Guest favourite
Guest house in Cape St. Claire
"The Cape Saint Claire Inn"
2 bedrooms, 2 beds, 2 private bathrooms
4–9 Oct
,
4.84 out of 5 average rating, 233 reviews
Photo 1 of 18
Featured hotel
Hotel in Annapolis
Governor Calvert king accessible
1 bedroom, 1 king bed, 1 bathroom
1–6 Nov
Photo 1 of 29
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
25–30 Oct
4.97 out of 5 average rating, 68 reviews
Photo 1 of 6
Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds, 2 bathrooms
31 Oct – 5 Nov
4.97 out of 5 average rating, 261 reviews
Photo 1 of 28
Guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
4.94 out of 5 average rating, 16 reviews
Photo 1 of 26
Home in Annapolis
The 1845 Outpost
3 bedrooms, 3 king beds, 2 bathrooms
25–30 Oct
New place to stay
Photo 1 of 24
Superhost
Home in Annapolis
Harbor’s Edge Retreat: Walk to Main St & Academy
3 bedrooms, 3 beds, 1.5 bathrooms
1–6 Oct
4.89 out of 5 average rating, 91 reviews
Photo 1 of 10
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, 229 reviews
Photo 1 of 28
Top guest favourite
Apartment in Annapolis
Funky Uptown Apt meets Downtown - Hist District
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
4.96 out of 5 average rating, 128 reviews
Photo 1 of 29
Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
4–9 Oct
New place to stay
Photo 1 of 12
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds, 1 bathroom
28 Dec – 2 Jan
4.97 out of 5 average rating, 465 reviews
Photo 1 of 29
Guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 2 beds, 1.5 bathrooms
25–30 Oct
4.92 out of 5 average rating, 97 reviews
Photo 1 of 9
Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 bathroom
4–9 Dec
4.96 out of 5 average rating, 269 reviews
Photo 1 of 29
Home in Annapolis
Beautiful 6BR home in Annapolis
6 bedrooms, 6 beds, 4 bathrooms
4–9 Oct
4.63 out of 5 average rating, 71 reviews
Photo 1 of 29
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
3–8 Oct
4.97 out of 5 average rating, 473 reviews
Photo 1 of 24
Top guest favourite
Home in Annapolis
The Red Door Cottage - Pet-Friendly!
2 bedrooms, 2 beds, 2 bathrooms
16–21 Nov
5.0 out of 5 average rating, 43 reviews
Photo 1 of 16
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 100 reviews
Photo 1 of 13
Top guest favourite
Flat in Annapolis
The Sail Loft
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 44 reviews
Photo 1 of 18
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
4.9 out of 5 average rating, 126 reviews