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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 private bathroom
27 Nov – 2 Dec
,
4.96 out of 5 average rating, 253 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bathroom
21–26 Aug
4.92 out of 5 average rating, 1132 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 469 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
23–28 Aug
4.93 out of 5 average rating, 85 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
29 Aug – 3 Sept
4.95 out of 5 average rating, 186 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
4.91 out of 5 average rating, 115 reviews
Top guest favourite
Guest house in Stevensville
Waterfront-View of Bay from your Bed
1 queen bed, 1 bathroom
21–26 Sept
4.99 out of 5 average rating, 360 reviews
Guest favourite
Guest house in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 210 reviews
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed, 1 bathroom
17–22 Oct
5.0 out of 5 average rating, 222 reviews
Hotel room in Annapolis
Governor Calvert King | Historic Inns
1 bedroom, 1 king bed, 1 bathroom
23–28 Aug
4.62 out of 5 average rating, 37 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 97 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
4.96 out of 5 average rating, 79 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 168 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
4.9 out of 5 average rating, 362 reviews
Top guest favourite
Home in Annapolis
Welcoming Luxury Estate for Family, Friends, Pets
7 bedrooms, 6 beds, 6.5 bathrooms
27 Oct – 1 Nov
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds, 1 bathroom
9–14 Sept
4.95 out of 5 average rating, 142 reviews
Top guest favourite
Home in Annapolis
Historic Home w/ Parking Steps From Capital & USNA
1 bedroom, 2 beds, 1.5 bathrooms
4–9 Oct
4.98 out of 5 average rating, 100 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, WC
17–22 Aug
4.93 out of 5 average rating, 60 reviews
Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds, 2 bathrooms
15–20 Aug
4.99 out of 5 average rating, 69 reviews