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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Townhouse in Annapolis
Moose’s Happy Place
3 bedrooms, 4 beds, 3.5 shared bathrooms
24–29 Nov
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5.0 out of 5 average rating, 113 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
16–21 Jul
4.92 out of 5 average rating, 74 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
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, 1 bathroom
20–25 Jul
4.95 out of 5 average rating, 132 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment
1 bedroom, 1 bed, 1 bathroom
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, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds, 2 bathrooms
11–16 Jul
4.96 out of 5 average rating, 70 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
26–31 Jul
4.95 out of 5 average rating, 180 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
19–24 Jul
4.93 out of 5 average rating, 179 reviews
Guest favourite
Guest house in Annapolis
"The Perch" - Hot Tub - Beach - Chesapeake Bay
1 bedroom, 1 queen bed, 1 bathroom
19–24 Jul
4.9 out of 5 average rating, 92 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
24–29 Jul
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds, 3 bathrooms
12–17 Sept
5.0 out of 5 average rating, 13 reviews
Guest favourite
Apartment in Annapolis
Semper Fi Condo
2 bedrooms, 3 queen beds, 2 bathrooms
26–31 Jul
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
4 bedrooms, 4 beds, 4 bathrooms
9–14 Jul
5.0 out of 5 average rating, 16 reviews
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, 10 reviews
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds, 2.5 bathrooms
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, 1 bathroom
12–17 Jul
4.85 out of 5 average rating, 124 reviews
Hotel room in Annapolis
Governor Calvert King | Historic Inns
1 bedroom, 1 king bed, 1 bathroom
16–21 Jul
4.55 out of 5 average rating, 31 reviews
Top guest favourite
Home in Annapolis
Quaint in the Heart of Annapolis
2 bedrooms, 2 double beds, 1 bathroom
24–29 Jul
5.0 out of 5 average rating, 113 reviews