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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
3–10 Oct
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4.98 out of 5 average rating, 165 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 72 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
16–21 Jul
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
4.97 out of 5 average rating, 461 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Aug
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Guest house in Stevensville
Waterfront-View of Bay from your Bed
4.99 out of 5 average rating, 350 reviews, 1 bed, 1 bathroom
7–12 Sept
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
4.99 out of 5 average rating, 155 reviews, 1 bed, 1 bathroom
9–14 Jul
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 6 beds, 3 bathrooms
12–17 Sept
Top guest favourite
Guest house in Annapolis
Eastport Gem ~ Walk to Downtown Annapolis
5.0 out of 5 average rating, 91 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
10–15 Jul
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
4.93 out of 5 average rating, 179 reviews, 1 queen bed, 1.5 bathrooms
19–24 Jul
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
4.93 out of 5 average rating, 27 reviews, 3 bedrooms, 2 bathrooms
5–10 Jul
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
4.95 out of 5 average rating, 180 reviews, 1 queen bed, 3 bathrooms
26–31 Jul
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment
4.9 out of 5 average rating, 103 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
4.92 out of 5 average rating, 89 reviews, 5 bedrooms, 9 beds, 3.5 bathrooms
5–10 Jul
Guest favourite
Home in Annapolis
Cozy Cottage
4.96 out of 5 average rating, 25 reviews, 2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
Guest favourite
Home in Annapolis
1 Block to USNA Stadium: Modern Annapolis Home!
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
4.92 out of 5 average rating, 1121 reviews, 1 bedroom, 2 beds, 1 bathroom
10–15 Aug
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
13–18 Jul
Top guest favourite
Home in Annapolis
DTA Row Home | Walk to City Dock & The Yard
5.0 out of 5 average rating, 15 reviews, 2 bedrooms, 3 beds, 2 bathrooms
11–16 Jul
Top guest favourite
Flat in Annapolis
Annapolis Main Street Modern Apartment
5.0 out of 5 average rating, 47 reviews, 2 bedrooms, 2 beds, 1 bathroom
7–12 Jul