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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Secluded Cottage_ A+ Amenities in Historic Dwntwn
2 bedrooms, 3 beds, 1 private bathroom
15–20 Jul
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4.93 out of 5 average rating, 223 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
27 Jul – 1 Aug
4.92 out of 5 average rating, 74 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bathroom
26–31 Jul
4.99 out of 5 average rating, 157 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, 462 reviews
Guest favourite
Home in Annapolis
1 Block to USNA Stadium: Modern Annapolis Home!
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 12 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, 180 reviews
Top guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
4 bedrooms, 6 beds, 2.5 bathrooms
23–28 Jul
5.0 out of 5 average rating, 21 reviews
Guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds, 2 bathrooms
11–16 Jul
4.96 out of 5 average rating, 72 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment
1 bedroom, 1 bed, 1 bathroom
12–17 Jul
4.9 out of 5 average rating, 104 reviews
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds, 2.5 bathrooms
12–17 Jul
5.0 out of 5 average rating, 9 reviews
Guest favourite
Apartment in Annapolis
Semper Fi Condo
2 bedrooms, 3 queen beds, 2 bathrooms
26–31 Jul
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds, 1 bathroom
9–15 Sept
4.95 out of 5 average rating, 134 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds, 3 bathrooms
12–17 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
12–17 Jul
4.93 out of 5 average rating, 28 reviews
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds, 2.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 12 reviews
Guest favourite
Townhouse in Annapolis
Perfect place for your family
3 bedrooms, 4 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 41 reviews
Hotel room in Annapolis
Historic Inn Stay | Steps from Maryland State
1 bedroom, 1 double bed, 1 bathroom
13–18 Jul
New place to stay
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
1–6 Aug
4.93 out of 5 average rating, 179 reviews