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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
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
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
23–28 Aug
4.93 out of 5 average rating, 191 reviews
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed, 1 bathroom
24–29 Aug
4.96 out of 5 average rating, 426 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
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, WC
18–23 Aug
4.92 out of 5 average rating, 61 reviews
Top guest favourite
Guest house in Annapolis
"The Perch" - Hot Tub - Beach - Chesapeake Bay
1 bedroom, 1 queen bed, 1 bathroom
28 Aug – 2 Sept
4.91 out of 5 average rating, 102 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
Room in Bowie
Cozy Private Queen Room | Free Parking | Near DC
1 queen bed, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Cottage in Edgewater
Waterview Studio on a sunset corner
1 bedroom, 1 queen bed, 1 bathroom
20–25 Aug
4.75 out of 5 average rating, 205 reviews
Top guest favourite
Home in Shady Side
Canary Pointe-A popular getaway for 2!
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 278 reviews
Top guest favourite
Flat in Chester
Cozy Waterfront Apartment Chester, MD
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.96 out of 5 average rating, 297 reviews
Top guest favourite
Guest suite in Arnold
Coastal Comfort Retreat near Annapolis, EV charger
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.94 out of 5 average rating, 222 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
19–24 Aug
4.95 out of 5 average rating, 210 reviews
Top guest favourite
Flat in Annapolis
Hillsmere Hideaway
1 bedroom, 2 beds, 1 bathroom
18–23 Aug
4.95 out of 5 average rating, 98 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
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, 470 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