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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Annapolis
Serene Riverfront Home
4 bedrooms, 5 beds, 3.5 private bathrooms
30 Aug – 4 Sept
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4.97 out of 5 average rating, 123 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
23–28 Aug
4.93 out of 5 average rating, 85 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 469 reviews
Guest favourite
Guest house in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 queen bed
16–21 Aug
4.95 out of 5 average rating, 210 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
6–11 Sept
4.98 out of 5 average rating, 63 reviews
Home in Annapolis
DTA - Park and Walk in safe, quiet neighborhood
2 bedrooms, 2 queen beds
16–21 Aug
New place to stay
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
16–21 Aug
4.93 out of 5 average rating, 190 reviews
Top guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
3 bedrooms, 4 beds
16–21 Aug
4.94 out of 5 average rating, 203 reviews
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed
24–29 Aug
4.96 out of 5 average rating, 423 reviews
Guest favourite
Flat in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
1 bedroom, 3 beds
16–21 Aug
4.92 out of 5 average rating, 520 reviews
Guest favourite
Townhouse in Annapolis
Annapolis Downtown Pleasant St Townhome 3 bedrooms
3 bedrooms, 3 beds
16–21 Aug
4.91 out of 5 average rating, 195 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Guest house in Stevensville
Private Guesthouse | 7-acres | Near wedding venues
2 bedrooms, 3 beds
15–20 Aug
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed
30 Aug – 4 Sept
4.91 out of 5 average rating, 115 reviews
Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed
15–20 Aug
4.9 out of 5 average rating, 49 reviews
Top guest favourite
Flat in Severna Park
Welcome to Anchors Aweigh!
1 bedroom, 3 beds
19–24 Aug
5.0 out of 5 average rating, 88 reviews
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds
21–26 Aug
4.96 out of 5 average rating, 114 reviews
Top guest favourite
Room in Annapolis
“Room at the Inn…”
1 queen bed
16–21 Aug
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds
15–20 Aug
4.98 out of 5 average rating, 41 reviews