
Vacation rentals in Hollywood, St. Mary's County
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Top-rated vacation rentals in Hollywood, St. Mary's County
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Popular amenities for Hollywood, St. Mary's County vacation rentals
Other great vacation rentals in Hollywood, St. Mary's County
Top guest favorite

Guest suite in Lusby
5 out of 5 average rating, 56 reviewsWelcome to Journey's End Hideaway!
Nicole JenniferRating, 5 stars6 days ago
Our stay was peaceful and relaxing. we loved sitting on the dock watching the birds and fish every morning and evening. Sunset is gorgeous.
Top guest favorite

Guest suite in Lusby
4.97 out of 5 average rating, 78 reviewsWaterfront on St. Leonard Creek at Fort Hill
LisaRating, 5 stars1 week ago
Living in the country, we like to find similar places to stay. We were not disappointed in the peaceful and quiet nature of this country Airbnb. If we are back in this area, we would check availability for this location first.

Houseboat in Hollywood
4.75 out of 5 average rating, 89 reviewsCharming Rustic Boathouse right on the Water!
NoahRating, 5 stars1 month ago
Barbara is a fantastic host. We’ve been coming to this quaint, serene, and beautiful place for years and have never been disappointed.
Top guest favorite

Apartment in Port Republic
4.97 out of 5 average rating, 206 reviewsSerenity Suite on Chesapeake Bay
KristaRating, 5 stars1 week ago
This is our second time staying at this cozy and tranquil retreat—and it won’t be our last. We first came here six months ago for a quiet getaway from the kids, and we liked it so much we knew we’d be back. This time was just as wonderful. The place is spotless, peaceful, and incredibly relaxing. The view of the bay is absolutely stunning—calm, quiet, and the perfect backdrop for unwinding. The hosts are warm and welcoming, and the space has everything you need for a comfortable and refreshing stay. If you’re looking for a serene escape with beautiful scenery and thoughtful touches, this is the place. We’re already planning our next visit.
Superhost

Home in Leonardtown
4.91 out of 5 average rating, 32 reviewsAbells Wharf Cottage - Natural Splendor Getaway
BrianRating, 5 stars8 months ago
We enjoyed our stay at Jan's cottage. Very clean, spacious and very good amenities. Jan was very responsive and informative on local places to visit/eat. The property is beautiful and peaceful. Just what we needed to have a relaxing weekend. Will visit again, Highly recommend!
Guest favorite

Home in Broomes Island
4.9 out of 5 average rating, 129 reviewsGorgeous Waterfront Home!
RichardRating, 5 stars5 months ago
Another lovely stay. Perfect for visiting relatives in the area. Thank-you Tom and Julie.
Top guest favorite

Guesthouse in Mechanicsville
4.99 out of 5 average rating, 88 reviewsBarnyard Retreat
AutumnRating, 5 stars1 month ago
I can’t say enough about the owners! Extremely helpful and nice. The pictures don’t do it justice. Very cozy and comfortable and it felt just like home! Will definitely be back soon!
Top guest favorite

Boat in Kinsale
5 out of 5 average rating, 8 reviewsSpend the Night on the River
AngelaRating, 5 stars5 days ago
What a fun, non traditional location for an overnight. Loved being on the water and close to the activities at The Slips. Annie was great at communication. Can’t wait to stay again.
Quick stats about vacation rentals in Hollywood, St. Mary's County
Total rentals
60 properties
Total number of reviews
2.5K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wifi availability
60 properties include access to wifi
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- Nationals Park
- The White House
- National Mall
- Georgetown University
- National Museum of African American History and Culture
- District Wharf
- Smithsonian National Museum of Natural History
- Sandy Point State Park
- Arlington National Cemetery
- Washington Monument
- Georgetown Waterfront Park
- National Air and Space Museum
- National Harbor
- Smithsonian American Art Museum
- Lincoln Park
- Meridian Hill Park
- Quiet Waters Park
- Lee's Hill Golfers' Club
- Maryland Renaissance Festival
- Flounder Pavilion Beach Front - Sandy Point State Park
- Library of Congress
- Gerry Boyle Park
- American African Museum
- Ragged Point Beach