Search results; Over 1,000 homes in Herald Harbor

Top guest favorite
Guesthouse in Crownsville
The Studio on the Severn (Waterfront)
1 bed
Aug 3 – 8
ﺩ.ﺇ3,563 for 5 nights
4.99 out of 5 average rating, 70 reviews
Guest favorite
Home in Crownsville
Welcome to Heron House! Annapolis Waterfront Oasis
Free cancellation
Sep 1 – 6
ﺩ.ﺇ9,342 for 5 nights
4.94 out of 5 average rating, 17 reviews
Guest favorite
Home in Crownsville
Severn River Waterfront Home
3 beds
Aug 10 – 15
ﺩ.ﺇ7,857 for 5 nights
4.94 out of 5 average rating, 165 reviews
Top guest favorite
Room in Severna Park
Stay with AndrewCustomer success,
Severna Park Private Entry Suite
Aug 4 – 9
ﺩ.ﺇ2,351 for 5 nights
4.94 out of 5 average rating, 16 reviews
Top guest favorite
Room in Pasadena
Stay with GloriaHosting for 6 years,
Pearl of the Magothy - Private Room 1
Aug 1 – 6
ﺩ.ﺇ1,705 for 5 nights
5.0 out of 5 average rating, 42 reviews
Top guest favorite
Home in Crownsville
"Hilltop Hideaway"- Private basement suite
Free cancellation
Aug 11 – 16
ﺩ.ﺇ2,368 for 5 nights
5.0 out of 5 average rating, 93 reviews
Top guest favorite
Apartment in Severna Park
Welcome to Anchors Aweigh!
3 beds
Aug 3 – 8
ﺩ.ﺇ3,552 for 5 nights
5.0 out of 5 average rating, 63 reviews
Top guest favorite
Guest suite in Severna Park
Waterfront Apt Near Annapolis -Boat Slip available
Free cancellation
Aug 1 – 6
ﺩ.ﺇ2,902 for 5 nights
4.98 out of 5 average rating, 61 reviews
Cottage in Severna Park
Colorful Round Bay Cottage
3 beds
Aug 17 – 22
ﺩ.ﺇ7,749 for 5 nights
4.8 out of 5 average rating, 30 reviews
Top guest favorite
Room in Arnold
Stay with MaureenHosting for 6 years,
Spacious room rental
Aug 1 – 6
ﺩ.ﺇ1,744 for 5 nights
4.97 out of 5 average rating, 37 reviews
Top guest favorite
Apartment in Annapolis
Oasis in the woods
3 beds
Aug 1 – 6
ﺩ.ﺇ4,844 for 5 nights
5.0 out of 5 average rating, 13 reviews
Guest favorite
Guesthouse in Severna Park
Private Severn Riverfront Guest Cottage
3 beds
Aug 4 – 9
ﺩ.ﺇ3,229 for 5 nights
4.98 out of 5 average rating, 84 reviews
Top guest favorite
Room in Arnold
Stay with MaureenHosting for 6 years,
Beautiful bedroom, beautiful view near Annapolis
Aug 2 – 7
ﺩ.ﺇ1,636 for 5 nights
4.97 out of 5 average rating, 76 reviews
Top guest favorite
Home in Annapolis
Welcoming Luxury Estate for Family, Friends, Pets
5 beds
Aug 18 – 23
ﺩ.ﺇ38,430 for 5 nights
5.0 out of 5 average rating, 7 reviews
Guest favorite
Guest suite in Arnold
Sunny Spot Suite, Serene, Annapolis, Naval Academy
Free cancellation
Aug 15 – 20
ﺩ.ﺇ2,635 for 5 nights
4.85 out of 5 average rating, 551 reviews
Home in Crownsville
2BR waterfront home with kayaks, firepit, & grill
3 beds
Sep 16 – 21
ﺩ.ﺇ10,367 for 5 nights
4.8 out of 5 average rating, 10 reviews
Guest favorite
Guest suite in Severna Park
Waterfront Studio near Annapolis (free kayak use)
Free cancellation
Aug 10 – 15
ﺩ.ﺇ2,691 for 5 nights
4.8 out of 5 average rating, 66 reviews
Top guest favorite
Guest suite in Arnold
Old Bay Bungalow
Free cancellation
Sep 7 – 12
ﺩ.ﺇ2,131 for 5 nights
4.96 out of 5 average rating, 685 reviews