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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
17–22 Nov
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4.96 out of 5 average rating, 254 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, WC
17–22 Aug
4.92 out of 5 average rating, 61 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
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
20–25 Sept
4.95 out of 5 average rating, 187 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed, 1 bathroom
23–28 Aug
4.89 out of 5 average rating, 369 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.92 out of 5 average rating, 1133 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
4.91 out of 5 average rating, 115 reviews
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds, 2 bathrooms
21–26 Aug
4.96 out of 5 average rating, 114 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, 86 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, 224 reviews
Top guest favourite
Home in Annapolis
Historic Home w/ Parking Steps From Capital & USNA
1 bedroom, 2 beds, 1.5 bathrooms
10–15 Nov
4.98 out of 5 average rating, 102 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
13–18 Sept
4.94 out of 5 average rating, 188 reviews
Home in Annapolis
City Gate Sanctuary
4 bedrooms, 4 beds, 3.5 bathrooms
27 Sept – 2 Oct
New place to stay
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
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
Guest favourite
Guest house in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 queen bed, 1 bathroom
18–23 Aug
4.95 out of 5 average rating, 210 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds, 3.5 bathrooms
13–18 Sept
4.91 out of 5 average rating, 91 reviews
Guest favourite
Home in Edgewater
House in Edgewater Maryland
5 bedrooms, 5 queen beds, 2 bathrooms
30 Aug – 4 Sept
4.91 out of 5 average rating, 192 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
18–23 Aug
4.94 out of 5 average rating, 32 reviews