Search results; Over 1,000 homes in Annapolis

Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 bed, 1 bathroom
10–15 Aug
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4.89 out of 5 average rating, 358 reviews
Top guest favourite
Flat in Annapolis
Perfect Eastport location
2 bedrooms, 3 beds
5–10 Jul
4.98 out of 5 average rating, 142 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds
10–15 Aug
4.92 out of 5 average rating, 1121 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
9–14 Jul
4.93 out of 5 average rating, 179 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
24–29 Jul
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds
9–14 Nov
4.97 out of 5 average rating, 454 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
13–18 Jul
4.98 out of 5 average rating, 57 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
16–21 Jul
4.92 out of 5 average rating, 72 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
14–19 Aug
4.97 out of 5 average rating, 461 reviews
Top guest favourite
Apartment in Annapolis
Cozy Annapolis Condo
2 bedrooms, 3 beds
28 Jul – 2 Aug
4.97 out of 5 average rating, 72 reviews
Top guest favourite
Home in Annapolis
Marymont Cottage
3 bedrooms, 3 beds
6–11 Jul
5.0 out of 5 average rating, 28 reviews
Guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds
25–30 Oct
4.96 out of 5 average rating, 240 reviews
Top guest favourite
Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
2 bedrooms, 4 beds
13–18 Jul
5.0 out of 5 average rating, 47 reviews
Guest favourite
Home in Annapolis
Cozy Cottage
2 bedrooms, 3 beds
5–10 Jul
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds
10–15 Jul
4.97 out of 5 average rating, 35 reviews
Guest favourite
Guest house in Annapolis
"The Perch" - Hot Tub - Beach - Chesapeake Bay
1 bedroom, 1 queen bed
11–16 Jul
4.9 out of 5 average rating, 92 reviews
Top guest favourite
Guest suite in Annapolis
Restful guest suite, scent-free, step-free
3 bedrooms, 3 queen beds
7–12 Jul
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds
16–21 Aug
4.96 out of 5 average rating, 154 reviews
Top guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
3 bedrooms, 3 beds
3–8 Jul
5.0 out of 5 average rating, 18 reviews