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Search results; Over 1,000 homes in Annapolis

Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 bed, 1 private bathroom
20–25 Sept
,
4.9 out of 5 average rating, 362 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, 192 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
Rooms in Edgewater
Cheerful 2 bedroom shared home with water views
2 bedrooms, 2 queen beds, 1 bathroom
22–27 Aug
4.86 out of 5 average rating, 93 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
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
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, 279 reviews
Guest favourite
Room in Annapolis
Kingfisher Room - Private Room w/ Bath, Annapolis
1 queen bed, 2.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 40 reviews
Top guest favourite
Room in Severna Park
Severna Park Private Entry Suite
2 beds, 1 bathroom
21–26 Aug
4.98 out of 5 average rating, 64 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, WC
28 Aug – 2 Sept
4.92 out of 5 average rating, 61 reviews
Guest favourite
Flat in Annapolis
Annapolis 4 Steps to Harbor Backs to Gate 1
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.91 out of 5 average rating, 32 reviews
Room in Bowie
Private Queen Room | Free Parking | Near DC | WiFi
1 bed, 1 bathroom
29 Aug – 3 Sept
New place to stay
Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds, 2 bathrooms
21–26 Aug
4.97 out of 5 average rating, 258 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
Flat in Severna Park
Welcome to Anchors Aweigh!
1 bedroom, 3 beds, 1 bathroom
21–26 Aug
5.0 out of 5 average rating, 88 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, 116 reviews
Guest favourite
Guest house in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 queen bed, 1 bathroom
22–27 Aug
4.95 out of 5 average rating, 210 reviews
Home in Annapolis
Getaway on the Bay - Waterfront Annapolis Escape
4 bedrooms, 5 beds, 3 bathrooms
23–28 Aug
New place to stay
Room in Bowie
Private Queen Room | Free Parking | Near DC| Wi-Fi
1 bed, 1 bathroom
23–28 Aug
New place to stay