Discover Your Perfect Hollywood Vacation Homes

Hollywood Luxury Rentals

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Hollywood Pet Friendly Vacation Rentals

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Why Choose Rent By Owner for your Hollywood Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Hollywood

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here can greatly enhance your experience, as seasonal variations in Hollywood, Maryland, influence everything from weather to local events, helping you select the perfect period to enjoy your stay.

Peak Season Highlights

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Summer (June to August)

During summer, the region experiences warm weather perfect for enjoying outdoor activities and water-based pursuits. This is the busiest time for visitors seeking a lively beach atmosphere and vibrant local events.

Average Temperature Daytime: 85°F - Nighttime: 70°F
autumn
Fall (September to November)

Fall attracts travelers with its mild temperatures and scenic coastal views, making it an ideal season for exploration and outdoor adventures in this area. The region's natural beauty peaks during this time, drawing many to enjoy the pleasant weather.

Average Temperature Daytime: 75°F - Nighttime: 55°F

Off-Season Highlights

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Winter (December to February)

In winter, the area experiences cooler temperatures and fewer tourists, offering a quieter and more relaxed experience for those seeking peaceful getaways. While some outdoor activities may be limited, this season provides an excellent opportunity for off-season tranquility.

Average Temperature Daytime: 50°F - Nighttime: 35°F
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Early Spring (March to April)

Early spring sees a gradual increase in temperatures and less tourist traffic, allowing you to enjoy the region's natural charm away from the crowds. It’s a perfect time to explore the outdoors comfortably before peak season begins.

Average Temperature Daytime: 60°F - Nighttime: 45°F

Weekly Weather Forecast for Hollywood

How to Book Your Hollywood Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Hollywood

More Top-Rated Vacation Rentals in Hollywood Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor dining with a furnished patio or deck for relaxing meals under the sun.
  • Take advantage of private or shared pools to cool off during warm summer days.
  • Experience scenic views and outdoor entertainment from outdoor fire pits or fireplaces.
  • Make the most of spacious yards or gardens perfect for outdoor activities and family gatherings.
  • Utilize community tennis courts, basketball courts, or other sports facilities available nearby.
  • Relax on hammock or lounge areas set up in lush landscaped gardens or shaded yards.
  • Explore nearby waterfront access or private docks if your rental offers direct waterway retreats.

Top Attractions Around Hollywood

What attractions are nearby?

Here, you can enjoy a variety of outdoor activities and local attractions that showcase the natural beauty and coastal charm of the region, making it an ideal destination for a memorable getaway.

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Family Activities

  • St. Clement's Island State Park: Explore this scenic park where you can enjoy outdoor activities, learn about local history, and take in beautiful river views.
  • Patuxent River Naval Air Museum: Discover the region’s military history through engaging exhibits and aircraft displays that captivate visitors of all ages.
  • Hollywood Volunteer Fire Department Museum: Visit this local museum to gain insight into community life and the area's emergency services history.
  • Beach Day at Chesapeake Bay: Spend quality family time relaxing on the sandy shores, swimming, or collecting shells along the calm waters of the bay nearby.
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Adult Activities

  • Visit the Patuxent River Naval Air Museum: Discover local maritime history and aviation exhibits that offer a fascinating glimpse into the region’s military heritage.
  • Explore Calvert Marine Museum: Enjoy engaging marine life displays, historic ships, and beautiful waterfront views in this educational attraction.
  • Enjoy Chesapeake Bay activities: Partake in boating, fishing, or simply relaxing by the water to take full advantage of the area's scenic coastline.
  • Experience local dining and breweries: Savor fresh seafood and regional brews at popular eateries within the area, perfect for unwinding after your day's adventures.

Other Places to Stay in Hollywood, MD

Greenwell State Park
Greenwell State Park Vacation Rentals
Sotterley Plantation
Sotterley Plantation Vacation Rentals
More Places to Stay Near Hollywood

Hollywood Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Options: Take advantage of the region's renowned eateries to enjoy authentic Maryland cuisine during your stay.
  • Plan Waterfront Activities: Engage in relaxing or adventurous activities along the area's scenic waterways, perfect for making the most of your vacation rental experience.
  • Visit Nearby Natural Attractions: Discover the region’s parks and outdoor spaces to immerse yourself in the natural beauty surrounding your holiday accommodations.
  • Utilize Local Transportation: Opt for convenient transportation options within the area to effortlessly explore popular attractions and hidden gems.

Transportation Options

  • Hollywood, Maryland Shuttle Services: This region offers reliable shuttle services that provide convenient transportation to local attractions and nearby cities.
  • Rental Car Options in Hollywood: Renting a car here allows you the freedom to explore the area at your own pace, with numerous rental agencies available close to key travel hubs.
  • Public Transit in Maryland’s Hollywood Area: Public buses operate within the region, offering an affordable way to get around and discover the local scenery.
  • Taxi and Rideshare Services in Hollywood: Taxis and ride-hailing services are readily accessible for quick, direct trips across this scenic destination and its surroundings.

Local Customs Options

  • Respect for Maritime Traditions: You will find that honoring the region's nautical heritage is a common custom, often reflected in local festivals and community events here.
  • Dining Etiquette: When visiting eateries, embracing casual yet polite dining manners is appreciated, especially during gatherings featuring fresh seafood from the Chesapeake Bay.
  • Community Engagement: Participating in neighborhood and regional activities fosters a genuine connection with locals in this coastal area.
  • Environmental Respect: Protecting the natural beauty of the area's waterways and parks is highly valued, so mindful behavior and sustainable practices are encouraged during your stay.

Frequently Asked Questions About Hollywood?

1. What are the top vacation rentals in Hollywood?

There are a lot of options in Hollywood. If you plan on staying in the Hollywood area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Hollywood:

2. Which vacation homes in Hollywood are best for families?

If you are looking for a family-friendly vacation home in Hollywood, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Hollywood:

3. How many Rentbyowner vacation rentals are available in Hollywood?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 54 in the Hollywood area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Hollywood. 

4. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary by listing, so it’s important to review the specific terms on each rental page. You can also contact the property owner directly for detailed information regarding cancellations and any applicable fees.

5. How do I secure my reservation for a vacation rental here?

Reservations are typically confirmed through an online booking process. To ensure your stay is secured, complete the reservation steps as outlined on the listing, and reach out to the host if you have any special requests or questions.

6. Are there specific check-in and check-out times I should be aware of?

Check-in and check-out times are set by each property owner and can differ from one rental to another. Be sure to review these details on the listing or contact the host in advance to coordinate your arrival and departure.

7. What amenities are usually included in vacation rentals in this region?

Amenities vary depending on the property, but most rentals offer essentials like Wi-Fi, parking, and kitchen facilities. Always verify the available amenities on the individual listing to ensure they meet your needs before booking.

8. Is there a reliable way to contact the owner if I have questions or need assistance during my stay?

Yes, most listings provide direct communication channels with the property owner or manager. You can reach out through the platform’s messaging system to ask questions or request support before and during your visit.