Vacation rentals in Hollywood, St. Mary's County

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Popular amenities for Hollywood, St. Mary's County vacation rentals

Stay near Hollywood, St. Mary's County's top sights

Jefferson Patterson Park & Museum23 locals recommend
Historic Sotterley Plantation7 locals recommend
Perigeaux Vineyards & Winery13 locals recommend
The Front Porch20 locals recommend
Port of Leonardtown Winery17 locals recommend
Veras Restaurant & Marina12 locals recommend

Other great vacation rentals in Hollywood, St. Mary's County

Guest favourite
Home in Montross
4.93 out of 5 average rating, 202 reviews

The Glebe

Irma VRating, 5 stars2 weeks ago
We loved the open space concept in the house. It has beautiful views and a fire pit. Beds were clean and comfortable. Very well supplied kitchen. We will come back. Thanks,
Top guest favourite
Home in Cambridge
5 out of 5 average rating, 34 reviews

Serene getaway with great waterfront views!

EugeniaRating, 5 stars7 months ago
We recently had a wonderful stay at Travis's place, and we couldn't have felt more at home. The house is not only beautiful but also comfortable, making it the perfect retreat. It’s one of the best-stocked homes I’ve encountered on Airbnb, which made our stay even more enjoyable. Travis was a wonderful host, always responsive and ready to assist with any questions. I truly hope to return in the future. Thank you, Travis, for hosting us in your lovely home!
Superhost
Home in Lusby
4.89 out of 5 average rating, 37 reviews

Waterfront home with three bedrooms,3 full baths

JoyceRating, 5 stars3 weeks ago
Perfect weekend away! The home backed up to the Chesapeake Bay. The home was very relaxing. Would definitely stay again!
Guest favourite
Home in Colonial Beach
4.94 out of 5 average rating, 68 reviews

The Heaven at Colonial Beach

MelissaRating, 5 stars3 months ago
I’ve stayed at a lot of Airbnb’s and this was easily one of the best. Everything was exactly as described, and maybe even better than described. It had tons of amenities and a well stocked kitchen perfect for our large family. Spotless and beautiful. I highly recommend this home and would gladly stay there again.
Top guest favourite
Home in Taylors Island
4.97 out of 5 average rating, 39 reviews

A Vacation for All, Away From It All

ChristyneRating, 5 stars5 months ago
If you are looking for a peaceful escape, you found it. Although this home can be used for large gatherings, it is also the perfect getaway for 2. My husband and I loved watching the water and the natural wildlife. DO NOT MISS THE OPPORTUNITY TO EXPERIENCE THIS HOUSE!
Guest favourite
Home in Leonardtown
4.87 out of 5 average rating, 15 reviews

Garden Getaway

LindsayRating, 5 stars2 months ago
We had the pleasure of staying here during the winter while we looked for a place to live. It was perfect! Quiet and peaceful yet super close to all restaurants and stores. We had some snowfall and the views were stunning! Once it warmed up we even got to see some wild life in the woods behind us. Lovely huge porch! Lots of space in garden escape. Can bring the entire family and more!!! Nice big driveway for easy turned around. Patrick was beyond responsive for all my questions.Whether is was just informing be as something as simple as an Internet outage in the area or we had one situation with an unsure smell. Patrick acted immediately on the problem and it was resolved within 2 hours from start to finish. Cannot recommend this place enough!
Guest favourite
Cottage in Leonardtown
4.92 out of 5 average rating, 143 reviews

Breton Breeze

PailinRating, 5 stars2 weeks ago
If you’re looking for a peaceful place to restore your soul and allow you to reconnect with nature, you’ll love Jan’s cozy waterside cottage. Beautifully decorated and well equipped, you’ll find everything you need provided for your stay. Thanks to Jan for sharing this special place!
Guest favourite
Home in Scotland
5 out of 5 average rating, 29 reviews

Bay Front Beach House

NicholasRating, 5 stars2 weeks ago
Wow what a view. Family had a wonderful stay. House is big and well equipped. Internet is strong and plenty of hot water for all. House has access to a private beach that the small grandkids enjoyed. Definitely would 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. Mechanicsville
  6. Hollywood