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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Charming City Oasis. Walk to harbor, eateries.USNA
4 bedrooms, 4 beds, 2 private bathrooms
8–13 Sept
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4.87 out of 5 average rating, 116 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
6–11 Sept
4.94 out of 5 average rating, 185 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, 466 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
5–10 Aug
4.98 out of 5 average rating, 162 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
24–29 Aug
4.98 out of 5 average rating, 62 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds
15–20 Aug
4.96 out of 5 average rating, 76 reviews
Top guest favourite
Guest suite in Annapolis
Charming Detached Studio w/ easy walk to Downtown.
1 bedroom, 1 queen bed
9–14 Aug
4.96 out of 5 average rating, 224 reviews
Room in Bowie
Private Queen Room | Free Parking | Near DC | WiFi
1 queen bed
7–12 Aug
New place to stay
Home in Annapolis
DTA - Park and Walk in safe, quiet neighborhood
2 bedrooms, 2 queen beds
9–14 Aug
New place to stay
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
20–25 Sept
4.95 out of 5 average rating, 184 reviews
Superhost
Home in Annapolis
The Corner House-Annapolis
3 bedrooms, 5 beds
10–15 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
10–15 Aug
4.89 out of 5 average rating, 366 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds
30 Sept – 5 Oct
5.0 out of 5 average rating, 21 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed
20–25 Sept
4.9 out of 5 average rating, 360 reviews
Top guest favourite
Room in Annapolis
“Room at the Inn…”
1 queen bed
9–14 Aug
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Room in Annapolis
Lovely Private Master Bedroom
1 queen bed
16–21 Aug
4.98 out of 5 average rating, 247 reviews
Guest favourite
Apartment in Annapolis
Renovated Apt In Historic Dist w/2 Parking Spots
2 bedrooms, 3 beds
10–15 Aug
4.94 out of 5 average rating, 446 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, 17 reviews