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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 private bathroom
25–30 Oct
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4.97 out of 5 average rating, 238 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
28 Jun – 3 Jul
4.95 out of 5 average rating, 179 reviews
Hotel room in Annapolis
Historic Inn Stay | Steps from Maryland State
1 bedroom, 1 double bed, 1 bathroom
21–26 Jun
New place to stay
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
26 Jun – 1 Jul
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
13–18 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
9–14 Jul
4.93 out of 5 average rating, 179 reviews
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, 99 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, 8 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 350 reviews
Guest favourite
Home in Annapolis
1 Block to USNA Stadium: Modern Annapolis Home!
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed, 1 bathroom
13–18 Jul
5.0 out of 5 average rating, 211 reviews
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds, 1 bathroom
20–25 Jul
4.95 out of 5 average rating, 129 reviews
Top guest favourite
Townhouse in Annapolis
Perfect place for your family
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Aug
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed, 1 bathroom
10–15 Aug
4.96 out of 5 average rating, 410 reviews
Top guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds, 2.5 bathrooms
22–27 Jul
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
5–10 Jul
4.91 out of 5 average rating, 68 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, 91 reviews
Guest favourite
Home in Cape St. Claire
Firepit + Basement Lounge + Putt Green | Sleeps 12
4 bedrooms, 6 beds, 2.5 bathrooms
28 Jun – 3 Jul
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds, 2.5 bathrooms
26 Jun – 1 Jul
4.97 out of 5 average rating, 35 reviews