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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Annapolis
Beach Access, Hot Tub, Pet Friendly, Fully Fenced
4 bedrooms, 4 beds, 2.5 private bathrooms
13–18 Sept
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4.99 out of 5 average rating, 139 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
16–21 Jul
4.92 out of 5 average rating, 74 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
26–31 Jul
4.99 out of 5 average rating, 156 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
14–19 Aug
4.97 out of 5 average rating, 461 reviews
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds
20–25 Jul
4.95 out of 5 average rating, 133 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment
1 bedroom, 1 bed
12–17 Jul
4.9 out of 5 average rating, 104 reviews
Guest favourite
Home in Annapolis
1 Block to USNA Stadium: Modern Annapolis Home!
2 bedrooms, 3 beds
12–17 Jul
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds
12–17 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Annapolis
Marymont Cottage
3 bedrooms, 3 beds
30 Jul – 4 Aug
5.0 out of 5 average rating, 28 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
26–31 Jul
4.95 out of 5 average rating, 180 reviews
Guest favourite
Apartment in Annapolis
Semper Fi Condo
2 bedrooms, 3 queen beds
26–31 Jul
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds
15–20 Aug
5.0 out of 5 average rating, 10 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
24–29 Jul
4.93 out of 5 average rating, 179 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
19–24 Jul
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds
13–18 Jul
5.0 out of 5 average rating, 12 reviews
Guest favourite
Flat in Annapolis
NEW lovely studio apartment with onsite parking!
1 bedroom, 1 queen bed
12–17 Jul
4.85 out of 5 average rating, 124 reviews
Top guest favourite
Home in Annapolis
Quaint in the Heart of Annapolis
2 bedrooms, 2 double beds
24–29 Jul
5.0 out of 5 average rating, 113 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms
12–17 Jul
4.93 out of 5 average rating, 28 reviews
Top guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
3 bedrooms, 3 beds
26–31 Jul
5.0 out of 5 average rating, 19 reviews