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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
,
4.98 out of 5 average rating, 165 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, 72 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
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
9–14 Jul
4.99 out of 5 average rating, 155 reviews
Top guest favourite
Guest house in Annapolis
Eastport Gem ~ Walk to Downtown Annapolis
1 bedroom, 2 beds
10–15 Jul
5.0 out of 5 average rating, 91 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
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
Firepit + Basement Lounge + Putt Green | Sleeps 12
4 bedrooms, 6 beds
4–9 Jul
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms
5–10 Jul
4.93 out of 5 average rating, 27 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
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
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds
5–10 Jul
4.92 out of 5 average rating, 89 reviews
Guest favourite
Home in Annapolis
Cozy Cottage
2 bedrooms, 3 beds
5–10 Jul
4.96 out of 5 average rating, 25 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, 103 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, 9 reviews
Top guest favourite
Flat in Annapolis
Upscale Condo In Annapolis w/Private Parking
2 bedrooms, 3 beds
5–10 Jul
4.96 out of 5 average rating, 28 reviews
Top guest favourite
Home in Annapolis
DTA Row Home | Walk to City Dock & The Yard
2 bedrooms, 3 beds
11–16 Jul
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Annapolis
Severn River Hope Cottage
3 bedrooms, 4 beds
13–18 Jul
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Flat in Annapolis
Annapolis Main Street Modern Apartment
2 bedrooms, 2 queen beds
7–12 Jul
5.0 out of 5 average rating, 47 reviews