Hollywood holiday lettings

We found 139 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Hollywood to find one that's perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a hot tub. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Hollywood

Showing deals for:14 Nov - 21 Nov

Image gallery for Resort Style Country Living on the Patuxent River

Miscellaneous
10 out of 10 rating
Exceptional
(14 reviews)

Resort Style Country Living on the Patuxent River

St. Leonard, MD

8% off
Price is £10,491
£1,499 per night
includes taxes & fees
Resort Style Country Living on the Patuxent River

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Hollywood

Find out more about Hollywood

Why people love visiting historical Hollywood

Enjoy the history and other features of Hollywood. Renowned for its restaurants, sporting events and shopping, this city welcomes all visitors. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Hollywood

Are you searching for things to do in the area? Venture out of your holiday home and check out everything that makes Hollywood a one-of-a-kind holiday spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Port of Leonardtown Winery (6 mi / 9.6 km)
  • Running Hare Vineyard (10.8 mi / 17.4 km)
  • Michael P. O'Brien Athletics and Recreation Center (14.2 mi / 22.8 km)
  • Maryland International Raceway (14.4 mi / 23.1 km)
  • Perigeaux Vineyards and Winery (5.4 mi / 8.8 km)
  • Wicomico Shores Golf Course (15.2 mi / 24.4 km)

Exploring the natural landscape of Hollywood

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Hollywood. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Annmarie Sculpture Garden and Arts Center (6.5 mi / 10.4 km)
  • St. Mary's River State Park (6.8 mi / 11 km)
  • Cove Point Park (8.4 mi / 13.5 km)
  • Flag Ponds Nature Park (8.7 mi / 13.9 km)
  • Seahorse Beach (8.9 mi / 14.3 km)
  • Battle Creek Cypress Swamp Sanctuary (9.2 mi / 14.8 km)

Transport options to and around Hollywood

Fly into Ronald Reagan National Airport (DCA), the closest airport, located 42.3 mi (68.1 km) from the city centre.

Frequently asked questions

What is the best area to stay in Hollywood when booking a holiday rental?
When considering a holiday rental in Hollywood, Maryland, a popular area to stay is the quaint neighbourhood surrounding St. Mary's River. This picturesque area offers a serene atmosphere, superb for those looking to relax while still being close to local attractions. The proximity to the river provides opportunities for various outdoor activities, such as kayaking and fishing, making it an ideal spot for nature lovers.

Another great option is the vicinity of the Hollywood Town Centre, which is vibrant and filled with charming shops and restaurants. Here, you'll find a welcoming community vibe, and it's a fantastic place to enjoy a leisurely stroll before popping into a local eatery. Just a short drive away, the historic St. Mary's City offers a fascinating glimpse into the region's past, with its living history museum and archaeological sites, making it a must-visit for history enthusiasts.
How much does it cost to rent a holiday home in Hollywood?
Prices for holiday rentals in Hollywood vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Hollywood to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Hollywood holiday house rentals?
You can find great discounts on house rentals in Hollywood on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Hollywood?
For renting a beach house in Hollywood, Maryland, the area around the Patuxent River offers some delightful options. The waterfront properties along the river provide stunning views and easy access to the water, superb for those looking to enjoy boating or fishing. Many of these rentals come equipped with amenities such as private docks, outdoor decks, and spacious living areas, ideal for families or groups wanting to relax by the water.

Additionally, the nearby Point Lookout State Park is a wonderful destination for nature lovers. Beach houses in this vicinity often feature outdoor spaces for barbecuing and entertaining, along with direct access to sandy shores for swimming and sunbathing. The park is also rich in history and offers trails for hiking and exploring the natural beauty of the area, making it a great complement to a beach getaway.
What is the most popular type of holiday rental accomodation in Hollywood?
In Hollywood, holiday houses are the most popular type of rental accommodation, with several available throughout the area. These properties are typically spacious and well-equipped, featuring multiple bedrooms, fully stocked kitchens, and comfortable living areas. Many holiday houses also come with private outdoor spaces, such as patios or gardens, allowing guests to enjoy the pleasant surroundings. This makes them an excellent choice for families or groups looking to relax after a day of exploring the nearby attractions and the beautiful Chesapeake Bay.
Are there any family house rentals in Hollywood?
In Hollywood, Maryland, there are several family-friendly house rentals available. Visitors will find accommodations in neighbourhoods that offer a peaceful atmosphere and convenient access to nearby attractions. Many homes feature spacious living areas, full kitchens for preparing meals, and outdoor spaces great for family gatherings or playtime.
Can I find long-stay holiday rentals in Hollywood?
A long-stay holiday rental in Hollywood is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Hollywood?
In Hollywood, Maryland, there are several pet-friendly house rentals available, offering a welcoming environment for travellers with furry companions. Many of these holiday homes are equipped with amenities such as fully stocked kitchens, comfortable living areas, and outdoor spaces great for relaxation. Some properties may even feature fenced yards, ensuring a safe area for pets to enjoy the outdoors.
Are there any remote work holiday rentals in Hollywood?
In Hollywood, Maryland, there are several remote work-friendly holiday rentals available, making it an ideal choice for those looking to blend work and leisure. These properties typically come equipped with essential amenities such as Wi-Fi, dedicated desks, and computer monitors, allowing for a productive work environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Hollywood holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Hollywood with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Hollywood?
In Hollywood, Maryland, popular holiday rental amenities include fully equipped kitchens, free WiFi, and essential appliances such as blenders and coffee makers. Most rentals provide cookware, dishware, and utensils, allowing guests to prepare their own meals with ease.
When is the best time to visit Hollywood for a holiday rental?
The best time to visit Hollywood, Maryland, is during the peak season from July to September, when the weather is warm and inviting, superb for beachgoers and outdoor enthusiasts alike. July, in particular, is the most popular month, drawing visitors eager to soak up the sun along the beautiful shores of the Patuxent River and partake in various local festivities. This lively atmosphere often includes outdoor concerts and family-friendly events, making it a prime time for those looking to create lasting memories.

Temperatures in July typically hover around the mid-30s Celsius, creating excellent conditions for swimming, kayaking, and exploring the nearby nature trails. The pleasant climate allows for comfortable outdoor activities, whether you're lounging on the beach or enjoying a sunset picnic.

For those who prefer a quieter experience, consider visiting in December. While this month falls into the low season, it offers a unique charm with fewer crowds and the opportunity to enjoy the peaceful winter landscape. You can still explore local attractions and take in the serene beauty of the area without the hustle and bustle of peak tourist traffic.
How early should I book a Hollywood holiday rental?
Book your Hollywood holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Hollywood?
In Hollywood, Maryland, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local culture. The picturesque Patuxent River offers opportunities for boating and fishing, making it a popular spot for water enthusiasts. The nearby St. Mary's River State Park features scenic trails superb for hiking and wildlife viewing, appealing to nature lovers.

For a taste of local history, the Historic St. Mary's City, located just a short drive away, provides insights into the early historic settlement and includes museums and archaeological sites. The charming waterfront area of Leonardtown is also close by, where travellers can explore quaint shops, dining options, and the vibrant town square.
Can I change or cancel my Hollywood home rental booking on Vrbo?
To find Hollywood holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Hollywood holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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