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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
20–25 Jul
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4.97 out of 5 average rating, 126 reviews
Home in Pasadena
Spacious Family Home in Pasadena
3 bedrooms, 4 beds
26–31 Jul
New place to stay
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
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
10–15 Aug
4.93 out of 5 average rating, 186 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds
30 Sept – 5 Oct
5.0 out of 5 average rating, 16 reviews
Home in Annapolis
Waterfront Gem w/ Dock: 2 Mi to Dwtn Annapolis!
4 bedrooms, 6 beds
1–6 Aug
New place to stay
Top guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds
18–23 Aug
4.96 out of 5 average rating, 111 reviews
Top guest favourite
Home in Annapolis
Cute bungalow blocks to Stadium
2 bedrooms, 3 beds
25–30 Jul
4.96 out of 5 average rating, 72 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
27 Jul – 1 Aug
4.98 out of 5 average rating, 60 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds
26–31 Jul
4.96 out of 5 average rating, 74 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
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds
16–21 Aug
5.0 out of 5 average rating, 13 reviews
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds
24–29 Jul
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms
26–31 Jul
4.93 out of 5 average rating, 30 reviews
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds
26–31 Jul
4.93 out of 5 average rating, 30 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
10–15 Aug
4.89 out of 5 average rating, 364 reviews
Top guest favourite
Home in Annapolis
2Bd Water View, w/Beach near Downtown Annapolis
2 bedrooms, 3 beds
22–27 Aug
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Annapolis
Nautical Retreat 6 Guests • 3 BDR • 2 Baths • Dogs
3 bedrooms, 3 beds
22–27 Aug
4.96 out of 5 average rating, 146 reviews