Discover Your Perfect Essex Vacation Homes

Essex Pet Friendly Vacation Rentals

See More Pet-Friendly Vacation Rentals in Essex on PetFriendly.io

Why Choose Rent By Owner for your Essex 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 Essex

When should you plan your Vacation Rentals stay?

Choosing the right time to visit ensures you experience the best of this destination, whether you're seeking a lively atmosphere or tranquil surroundings within the region, so consider seasonal trends and local events when planning your stay.

Peak Season Highlights

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Summer (June to August)

During the summer months, this destination experiences warm weather that is perfect for enjoying outdoor activities. The region attracts visitors seeking a lively atmosphere and longer daylight hours.

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

Autumn brings mild temperatures and scenic foliage, making it an ideal time for sightseeing and outdoor excursions in the area. Visiting during this season allows you to experience the changing scenery at its best.

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

Off-Season Highlights

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Winter (December to February)

In winter, the region tends to be quieter with cooler temperatures, providing a peaceful retreat. It's a good time for travelers looking to enjoy the area without the crowds and at lower rates.

Average Temperature Daytime: 45°F - Nighttime: 30°F
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Early Spring (March to May)

As the region transitions into spring, temperatures are still cool but gradually warming. This season offers a quiet atmosphere for those who prefer fewer tourists and more affordable accommodations.

Average Temperature Daytime: 60°F - Nighttime: 40°F

Weekly Weather Forecast for Essex

How to Book Your Essex 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 Essex

More Top-Rated Vacation Rentals in Essex 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 a private outdoor patio or deck perfect for relaxing and entertaining.
  • Take advantage of a well-maintained backyard ideal for outdoor activities or family gatherings.
  • Look for access to scenic walking trails or nature paths nearby to explore the region’s natural beauty.
  • Relax in a furnished outdoor seating area that provides a comfortable space to unwind after your adventures.
  • Benefit from outdoor grilling facilities to prepare delicious meals with locally sourced ingredients.
  • Find parking options that include dedicated outdoor spaces to make your stay more convenient.
  • Discover outdoor recreational amenities such as a boat dock or fishing spots, perfect for this waterside destination.

Top Attractions Around Essex

What attractions are nearby?

While staying here, you can enjoy a variety of nearby activities in Essex, Maryland, including exploring scenic waterfront parks, engaging in outdoor recreational pursuits, and experiencing local dining options that showcase the region's charm.

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Family Activities

  • Hunt Valley Heritage Museum: Discover local history and engage in family-friendly exhibits that highlight the region’s rich cultural background.
  • Mariner Point Park: Enjoy outdoor activities like picnicking, fishing, and exploring scenic trails along the Chesapeake Bay with your loved ones.
  • Sparrows Point Golf Course: Introduce the whole family to the game of golf at this nearby course designed for players of all skill levels.
  • Essex Community Center: Participate in various recreational programs and indoor activities suitable for kids and adults alike in the area.
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Adult Activities

  • Fort McHenry National Monument and Historic Shrine: Discover the history and enjoy scenic views at this iconic site, just a short drive from your Essex vacation rental.
  • Back River Community Park: Relax in the natural surroundings with walking trails, fishing spots, and picnic areas, perfect for unwinding during your stay.
  • Essex Sky Park: Experience the beauty of the region from above by taking a scenic flight or enjoying the park's open spaces for outdoor activities.
  • Sailing and Boating on the Chesapeake Bay: Engage in water-based adventures, with easy access to boat rentals and marinas nearby for a memorable day on the water.

Other Places to Stay in Essex, MD

Essex Marina
Essex Marina Vacation Rentals
Rocky Point Golf Course
Rocky Point Golf Course Vacation Rentals
Rocky Point Park and Beach
Rocky Point Park and Beach Vacation Rentals
More Places to Stay Near Essex

Essex Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Options: Get to know the area's vibrant culinary scene by trying local restaurants that highlight regional flavors and fresh ingredients.
  • Visit Waterfront Areas: Make the most of your stay by spending time along the waterfront, where you can enjoy scenic views and relaxing activities.
  • Plan Outdoor Activities: Take advantage of nearby parks and nature spots to experience outdoor adventures that showcase the natural beauty of this region.
  • Discover Cultural Experiences: Immerse yourself in the local culture through festivals, galleries, or historical sites that offer unique insights into the destination's heritage.

Transportation Options

  • Severna Park Trolley Service: This local trolley offers convenient transportation within the area, making it easy to explore nearby attractions and amenities.
  • Baltimore/Washington International Thurgood Marshall Airport (BWI): As the region’s major airport, BWI provides numerous domestic flights, simplifying travel to and from Essex and its surroundings.
  • MD Transit Bus Services: The regional bus network connects here with key locations across Maryland, offering an affordable and reliable way to get around the area.
  • Rental Car Services: Several rental agencies operate nearby, providing flexible transportation options for exploring the region at your own pace.

Local Customs Options

  • Seafood Dining Etiquette: When visiting local eateries in the area, you'll notice an emphasis on fresh seafood, with diners often sharing dishes and engaging in friendly conversations about the region's culinary traditions.
  • Participating in community events or festivals here provides a chance to experience the area's rich maritime history and enjoy traditional Chesapeake Bay celebrations.
  • Respect for Local Waterfront Customs: As you explore the waterfront, it's customary to observe quiet enjoyment of the scenery and adhere to guidelines that protect natural and public spaces.
  • Support of Local Artisans and Markets: Visitors are encouraged to engage with local markets and artisans, valuing handmade crafts and regional specialties as part of authentic experiences here.

Essex Vacation Rental Frequently Asked Questions

1. What are the top vacation rentals in Essex?

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

2. How many vacation rentals have private pools in Essex?

There are 5 vacation rentals with private pools near Essex. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Essex are best for families?

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

4. How many Rentbyowner vacation rentals are available in Essex?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 116 in the Essex 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 Essex. 

5. What is the cancellation policy for vacation rentals in Essex, Maryland?

The cancellation policy varies by property. To ensure you understand the specific terms, please review the listing details or contact the property owner directly before booking.

6. Are there any restrictions or requirements for booking a vacation rental in Essex, Maryland?

Restrictions and requirements depend on each individual rental. You should read the specific listing information or communicate with the property owner to confirm any age limits, pet policies, or other criteria.

7. How do I find the most suitable vacation rental in Essex, Maryland?

You can filter search results based on your preferences, such as amenities, price range, and location within the area. For personalized recommendations, reaching out to hosts can also help find the perfect fit for your stay.

8. What is the check-in and check-out process for vacation rentals here?

The check-in and check-out procedures are set by each host. Details are typically provided in the listing or communicated directly, so it’s best to review those specifics or contact the owner for clarification.

9. Is there a secure way to pay for my Essex, Maryland vacation rental reservation?

Payment methods are handled through a trusted platform that ensures your financial information remains protected. Always confirm the accepted payment options listed in the property listing or ask the owner if you have questions.