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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Flat in Annapolis
CIRCA 1885-Historic Annapolis-USNA GATE 1
2 bedrooms, 2 beds, 1 private bathroom
9–14 Aug
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4.99 out of 5 average rating, 129 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
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, 1.5 bathrooms
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, 1 bathroom
14–19 Aug
4.97 out of 5 average rating, 463 reviews
Superhost
Home in Annapolis
Luxury Eastport Home w/ Chef’s Kitchen, Sleeps 16
3 bedrooms, 12 beds, 4.5 bathrooms
26–31 Jul
4.88 out of 5 average rating, 50 reviews
Top guest favourite
Guest house in Annapolis
"The Perch" - Hot Tub - Beach - Chesapeake Bay
1 bedroom, 1 queen bed, 1 bathroom
26–31 Jul
4.91 out of 5 average rating, 95 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
10–15 Aug
4.93 out of 5 average rating, 183 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds, 3 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bathroom
26–31 Jul
4.98 out of 5 average rating, 160 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 93 reviews
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds, 2.5 bathrooms
26–31 Jul
4.93 out of 5 average rating, 30 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
19–24 Jul
4.93 out of 5 average rating, 29 reviews
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds, 2.5 bathrooms
18–23 Jul
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Annapolis
Nautical Retreat 6 Guests • 3 BDR • 2 Baths
3 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
4.96 out of 5 average rating, 146 reviews
Superhost
Flat in Annapolis
Modern Eastport Getaway, Near Historic Annapolis
1 bedroom, 3 beds, 1 bathroom
19–24 Jul
4.84 out of 5 average rating, 19 reviews
Top guest favourite
Home in Annapolis
Cute bungalow blocks to Stadium
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Jul
4.96 out of 5 average rating, 72 reviews
Top guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed, 1 bathroom
21–26 Jul
4.96 out of 5 average rating, 130 reviews
Guest favourite
Home in Annapolis
Stay Retro Naptown
4 bedrooms, 4 queen beds, 2 bathrooms
24–29 Jul
4.95 out of 5 average rating, 80 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, 182 reviews