Vacation rentals in Hollywood, St. Mary's County

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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
A waterfront view is captured at sunset, highlighting a charming lighthouse structure with lights glowing from its windows. Several boats are docked along the wooden pier, creating a serene scene as the vibrant sun descends, reflecting off the calm water.
Guest suite in Lusby
5 out of 5 average rating, 56 reviews

Welcome 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
A metal pot filled with various blue crabs, showcasing their characteristic blue claws and greenish shells. The crabs are arranged closely together, emphasizing their natural coloration and texture.
Guest suite in Lusby
4.97 out of 5 average rating, 78 reviews

Waterfront 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.
A wooden dock extends towards a charming boathouse, showcasing large windows that offer views of the surrounding nature. The brown and grey structures blend with the autumn foliage, enhancing the peaceful lakeside setting. Adirondack chairs line the dock, inviting relaxation by the water.
Houseboat in Hollywood
4.75 out of 5 average rating, 89 reviews

Charming 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
A wooden swinging bench is suspended under a wooden structure, surrounded by lush green grass and mature trees. Views of the bay can be seen in the background, providing a serene setting for relaxation.
Apartment in Port Republic
4.97 out of 5 average rating, 206 reviews

Serenity 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
Two piers extend into the calm water, reflecting hues of orange and pink from the sunset in the background. The wooden beams of the piers create a rustic look against the serene bay, framed by lush greenery along the shoreline.
Home in Leonardtown
4.91 out of 5 average rating, 32 reviews

Abells 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 reviews

Gorgeous 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
A quaint structure features a rustic wooden exterior with visible weathering and a bright teal door. Lush greenery surrounds the entrance, creating a natural setting. A welcome mat is positioned at the door, indicating an inviting access point.
Guesthouse in Mechanicsville
4.99 out of 5 average rating, 88 reviews

Barnyard 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
A modern bathroom features three round mirrors above a double sink vanity with brushed metal faucets. The space incorporates navy blue cabinetry and light-colored stone countertops. A separate shower area is visible, with a textured wall and wooden bench, on the right side of the image.
Boat in Kinsale
5 out of 5 average rating, 8 reviews

Spend 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

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. St. Mary's County
  5. Hollywood