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Best Vacation Homes in Assateague Island

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Assateague Island Pet Friendly Vacation Rentals

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10.0 (1 Review)
House
Gallops Point
  • Air Conditioner
  • Parking
  • Pet Friendly
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Why Choose Rent By Owner for your Assateague Island 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.

Popular Areas for Assateague Island Vacation Rentals

Where are the best neighborhoods to stay in Assateague Island?

When planning your stay on Assateague Island, choosing the right neighborhood can enhance your experience amidst its natural beauty. Whether you prefer to be close to pristine beaches or nestled within peaceful, scenic areas, the neighborhoods around Assateague Island offer a variety of options for every traveler. These regions provide convenient access to outdoor adventures and serene settings, making them ideal for those seeking a relaxing getaway. Discover the perfect spot to book your vacation rental, ensuring a comfortable and memorable visit to this unique destination.

West Ocean City

This area offers convenient access to the natural beauty and outdoor activities of Assateague Island, making it an ideal base for exploring Maryland's coastal attractions. Here, you’ll find comfortable vacation rentals that provide a relaxing retreat close to the region’s popular beaches and local amenities.

View 34+ Rentals in West Ocean City

Piney Island

Located near Chincoteague, this destination provides a peaceful setting with easy access to the scenic shores and wildlife of Assateague Island. Staying here allows you to experience the tranquility of Virginia’s coastal environment while enjoying the comfort of well-appointed vacation rentals.

View 775+ Rentals in Piney Island

Best Times to Visit Assateague Island

When should you plan your Vacation Rentals stay?

To make the most of your visit, consider planning your stay during the shoulder seasons when the area offers pleasant weather and fewer crowds, enhancing your experience of this charming coastal destination.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this period, the region experiences warm temperatures and less crowded beaches, making it ideal for a peaceful beach getaway.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
summer
Mid-Summer (July to August)

This is the busiest time when the weather is hot and perfect for outdoor activities, attracting families and outdoor enthusiasts alike.

Average Temperature Daytime: 85°F to 90°F - Nighttime: 60°F to 70°F

Off-Season Highlights

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Early Spring (March to April)

Visit during the early spring months for a quieter experience with mild weather perfect for exploring the natural scenery.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 45°F to 55°F
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Fall (September to October)

The fall offers serene landscapes and fewer visitors, providing a tranquil setting to enjoy the area's natural beauty before winter arrives.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F

Weekly Weather Forecast for Assateague Island

How to Book Your Assateague Island 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 Assateague Island

More Top-Rated Vacation Rentals in Assateague Island 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 easy access to outdoor grilling areas for preparing seaside meals.
  • Take advantage of spacious decks or patios to relax and soak in the natural surroundings.
  • Benefit from available outdoor showers, perfect for rinsing off after a day at the beach.
  • Access private or community pools to cool off during warm days in the region.
  • Utilize well-maintained picnic areas for outdoor dining amidst scenic views.
  • Explore nearby walking paths or nature trails right from your rental’s doorstep.
  • Make use of designated parking spaces to conveniently park your vehicle close to the property.

Top Attractions Around Assateague Island

What attractions are nearby?

During your stay, you'll find a variety of outdoor activities nearby, including beachcombing, birdwatching, and kayaking, all perfect for exploring the natural beauty of this coastal destination.

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Family Activities

  • Wild Horse Viewing Tours: Embark on a family-friendly adventure to observe the iconic wild horses roaming freely across the region, offering memorable photo opportunities and a glimpse into the area's natural beauty.
  • Beach Activities and Sandcastle Building: Spend your days relaxing on the pristine sands, where you can enjoy swimming, sunbathing, or engaging in creative sandcastle building with your loved ones.
  • Nature Trails and Bird Watching: Explore scenic nature trails perfect for family walks and discover diverse bird species that thrive in this coastal habitat, making it an educational experience for young explorers.
  • Educational Visitor Centers: Visit local visitor centers that provide interactive exhibits and programs about the area's wildlife and history, enhancing your family's understanding of this unique destination.
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Adult Activities

  • Wildlife Watching: Embark on a guided tour or explore independently to observe the famous wild horses that roam freely across this destination's protected landscapes.
  • Birding Excursions: Take advantage of the region's diverse habitats to spot a variety of bird species, making it an ideal activity for nature enthusiasts staying nearby.
  • Fishing Opportunities: Cast a line in the area's saltwater and freshwater spots, renowned for their abundant fish populations suitable for anglers of all skill levels.
  • Beach Activities for Adults: Enjoy relaxing walks, sunbathing, or beachcombing along the pristine shores that are perfect for unwinding during your stay here.

Other Places to Stay in Assateague Island, MD

Assateague Island National Seashore
Assateague Island National Seashore Vacation Rentals
Assateague Lighthouse
Assateague Lighthouse Vacation Rentals
Chincoteague National Wildlife Refuge
Chincoteague National Wildlife Refuge Vacation Rentals
Assateague Point
Assateague Point Vacation Rentals
Assateague State Park
Assateague State Park Vacation Rentals
More Places to Stay Near Assateague Island

Assateague Island Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Wildlife Encounters: Keep a respectful distance from the iconic wild horses and other wildlife that roam here, ensuring your experience remains safe and enjoyable.
  • Explore Nature Trails Early: Take advantage of the region’s scenic trails during the early morning hours to observe the area's diverse birdlife and pristine natural beauty.
  • Utilize Local Resources: Visit the nearby visitor centers to gather maps, trail information, and tips that will enhance your outdoor explorations in this coastal destination.
  • Book Your Stay in Advance: Secure your ideal vacation rental early to enjoy the most popular spots in this destination and guarantee a seamless holiday experience.

Transportation Options

  • Personal Vehicle: Traveling by car offers the flexibility to explore the island’s natural beauty at your own pace, with ample parking available near popular spots.
  • Shuttle Services: Organized shuttle services provide convenient transportation from nearby towns directly to the island, making for a hassle-free journey.
  • Bicycle Rentals: Biking is an eco-friendly and enjoyable way to navigate the scenic areas and discover hidden corners here on this destination.
  • Public Transit: Bus routes serve the region efficiently, connecting you to key access points and helping you reduce travel costs during your stay.

Local Customs Options

  • Wild Horse Encounters: Respect the local wild horses that roam freely here, and observe from a distance to ensure their safety and yours.
  • Shell Collecting Customs: When collecting shells along the shoreline, be mindful of local regulations and avoid disturbing the natural habitat.
  • Campfire Etiquette: If you choose to enjoy a campfire, adhere to designated areas and fire safety practices to preserve the area's natural beauty.
  • Leave No Trace: Practice responsible tourism by cleaning up after yourself and leaving the pristine environment unchanged for future visitors.

Assateague Island Vacation Rental Frequently Asked Questions

1. What are the top vacation rentals in Assateague Island?

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

2. How many vacation rentals have private pools in Assateague Island?

There are 40 vacation rentals with private pools near Assateague Island. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Assateague Island are best for families?

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

4. How many Rentbyowner vacation rentals are available in Assateague Island?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1113 in the Assateague Island 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 Assateague Island. 

5. What is the cancellation policy for vacation rentals near Assateague Island?

Cancellation policies vary by property. You should review the specific listing details or contact the property owner directly to understand the terms and any applicable fees before making your reservation.

6. Are there any additional fees I should be aware of when booking a vacation rental in this area?

Additional fees such as cleaning, service charges, or taxes are often included in the listing details. It's recommended to check the property’s description or contact the owner for transparency on all costs associated with your stay.

7. How do I confirm my reservation and what is the check-in process?

Once you book a vacation rental here, you'll receive confirmation details from the host. Check-in procedures are typically outlined in your reservation confirmation or provided by the property owner, so reviewing these details in advance ensures a smooth arrival.

8. Can I modify or extend my booking for a vacation rental in the region?

Modifications or extensions depend on the property's availability and the owner's policies. Contact the host directly through the listing to discuss your needs and arrange any changes to your stay.

9. What amenities are typically included in vacation rentals around Assateague Island?

Amenities vary by property but often include essentials like Wi-Fi, kitchen facilities, linens, and outdoor spaces. To ensure the rental meets your expectations, review the listing details carefully and reach out to the owner if you have specific requirements.

Assateague Island Top Rated Vacation Rentals

See More Assateague Island Vacation Rentals