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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Apartment in Annapolis
New Downtown Annapolis Condo With Free Parking
2 bedrooms, 2 beds, 2 private bathrooms
15–20 Nov
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4.98 out of 5 average rating, 165 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
16–21 Aug
4.93 out of 5 average rating, 187 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 31 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
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, 184 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, 84 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
5.0 out of 5 average rating, 17 reviews
Guest favourite
Guest house in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 queen bed, 1 bathroom
11–16 Aug
4.95 out of 5 average rating, 209 reviews
Guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
4 bedrooms, 6 beds, 2.5 bathrooms
10–15 Aug
4.92 out of 5 average rating, 25 reviews
Guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
3 bedrooms, 4 beds, 2.5 bathrooms
16–21 Aug
4.94 out of 5 average rating, 202 reviews
Top guest favourite
Home in Annapolis
Newly Renovated Downtown Charm, Game Room, Patio
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
29 Aug – 3 Sept
4.98 out of 5 average rating, 63 reviews
Guest favourite
Home in Riva
Waterfront Annapolis Getaway!
1 bedroom, 1 king bed, 2.5 bathrooms
7–12 Sept
4.92 out of 5 average rating, 95 reviews
Top guest favourite
Home in Annapolis
Villa Annapolitana • Parking 1 min • USNA 4 min
3 bedrooms, 3 beds, 2.5 bathrooms
10–15 Aug
4.97 out of 5 average rating, 152 reviews
Top guest favourite
Home in Annapolis
Elegant & Authentic Annapolis
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 153 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
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.96 out of 5 average rating, 224 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
6–11 Sept
4.94 out of 5 average rating, 185 reviews
Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.89 out of 5 average rating, 47 reviews