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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Apartment in Annapolis
1 bedroom -king in Annapolis- low cleaning fee
1 bedroom, 3 beds, 1 private bathroom
18–23 Jul
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4.97 out of 5 average rating, 125 reviews
Superhost
Home in Annapolis
Luxury Eastport Home w/ Chef’s Kitchen, Sleeps 16
3 bedrooms, 12 beds
26–31 Jul
4.88 out of 5 average rating, 50 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
16–21 Aug
4.93 out of 5 average rating, 180 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
30 Jul – 4 Aug
4.92 out of 5 average rating, 78 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, 463 reviews
Cottage in Pasadena
Private Chesapeake Retreat | Firepit, Kayaks, View
1 bedroom, 2 beds
19–24 Jul
New place to stay
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
10–15 Aug
4.93 out of 5 average rating, 183 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
26–31 Jul
4.98 out of 5 average rating, 160 reviews
Guest favourite
Home in Annapolis
Stay Retro Naptown
4 bedrooms, 4 queen beds
24–29 Jul
4.95 out of 5 average rating, 80 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds
16–21 Aug
4.97 out of 5 average rating, 93 reviews
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds
23–28 Aug
4.98 out of 5 average rating, 40 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, 16 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms
19–24 Jul
4.93 out of 5 average rating, 29 reviews
Top guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed
21–26 Jul
4.96 out of 5 average rating, 130 reviews
Superhost
Home in Annapolis
*NEW* Beautiful, Walkable Home Near Town/USNA
3 bedrooms, 4 beds
5–10 Aug
New place to stay
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
10–15 Aug
4.89 out of 5 average rating, 362 reviews
Superhost
Flat in Annapolis
Charming Eastport
1 bedroom, 1 queen bed
26–31 Jul
4.77 out of 5 average rating, 298 reviews
Superhost
Flat in Annapolis
Modern Eastport Getaway, Near Historic Annapolis
1 bedroom, 3 beds
19–24 Jul
4.84 out of 5 average rating, 19 reviews
Top 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, 12 reviews