Best Vacation Homes in Assateague Island
New
House
3 Bedrooms
3 Baths
6 Guests
2322 ft²
Fireplace/Heating
Kitchen
Parking
Air Conditioner
R12,797/Night
7 Nights - R89,584
House
10.0(6 Reviews)
2 Bedrooms
1 Bath
6 Guests
1797.57 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
Internet
R2,519/Night
7 Nights - R17,633
Cottage
10.0(1 Review)
1 Bedroom
1 Bath
Oceanfront
Ocean View
View- Kitchen
R2,802/Night
7 Nights - R19,611
New
House
4 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
Balcony/Terrace- Kitchen
- Parking
R8,102/Night
7 Nights - R56,707
House
10.0(4 Reviews)
2 Bedrooms
2 Baths
5 Guests
1603.82 ft²
- Fireplace/Heating
- Parking
- Internet
Child Friendly
R3,312/Night
7 Nights - R23,187
New
House
3 Bedrooms
1 Bath
6 Guests
1200 ft²
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
R7,768/Night
7 Nights - R54,383
New
House
3 Bedrooms
2 Baths
8 Guests
2200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R6,985/Night
7 Nights - R48,895
New
House
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
R5,433/Night
7 Nights - R38,035
Assateague Island Luxury Rentals
House
9.8(29 Reviews)
8 Bedrooms
7 Baths
16 Guests
4994 ft²
- Oceanfront
Hot Tub- Fireplace/Heating
- Ocean View
R42,954/Night
7 Nights - R300,673
House
10.0(1 Review)
5 Bedrooms
1 Bath
12 Guests
Private Pool- Hot Tub
- Fireplace/Heating
Pool
R20,638/Night
7 Nights - R144,462
House
10.0(1 Review)
4 Bedrooms
5 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
R19,872/Night
7 Nights - R139,106
House
9.8(14 Reviews)
4 Bedrooms
4 Baths
8 Guests
2000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
R18,041/Night
7 Nights - R126,284
House
4 Bedrooms
5 Baths
10 Guests
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
R17,993/Night
7 Nights - R125,955
House
5 Bedrooms
1 Bath
15 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R17,844/Night
7 Nights - R124,900
House
10.0(1 Review)
4 Bedrooms
5 Baths
10 Guests
4546 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R16,614/Night
7 Nights - R116,298
R14,937/Night
7 Nights - R104,564
Assateague Island Pet Friendly Vacation Rentals
House
10.0(81 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
R4,229/Night
7 Nights - R29,598
House
10.0(1 Review)
1 Bedroom
3 Baths
6 Guests
1797.57 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R5,351/Night
7 Nights - R37,459
House
10.0(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R5,080/Night
7 Nights - R35,563
House
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
1463.89 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
R7,301/Night
7 Nights - R51,104
House
10.0(9 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R7,035/Night
7 Nights - R49,242
House
10.0(8 Reviews)
2 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R6,533/Night
7 Nights - R45,731
House
10.0(6 Reviews)
2 Bedrooms
2 Baths
6 Guests
1800 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
R4,923/Night
7 Nights - R34,459
House
10.0(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
964 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R4,148/Night
7 Nights - R29,037
Assateague Island Large Vacation Homes
Villa
10.0(6 Reviews)
2 Bedrooms
1 Bath
6 Guests
540 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R5,693/Night
7 Nights - R39,848
House
10.0(2 Reviews)
3 Bedrooms
1 Bath
10 Guests
- Pool
- Parking
- Air Conditioner
- Internet
R2,835/Night
7 Nights - R19,842
Villa
10.0(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
540 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R4,697/Night
7 Nights - R32,877
House
Chincoteague Island Beach House - Sir Whelk-A-Lot - New! - Downtown Location! Bikes & Yaks Included!
10.0(1 Review)
3 Bedrooms
2 Baths
10 Guests
1216.32 ft²
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
R4,565/Night
7 Nights - R31,954
House
10.0(2 Reviews)
2 Bedrooms
2 Baths
11 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R7,378/Night
7 Nights - R51,648
Villa
10.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
540 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R6,675/Night
7 Nights - R46,720
Villa
9.6(14 Reviews)
2 Bedrooms
1 Bath
4 Guests
540 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R2,201/Night
7 Nights - R15,409
Villa
9.6(7 Reviews)
2 Bedrooms
1 Bath
6 Guests
540 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R5,693/Night
7 Nights - R39,848
Why Choose Rent By Owner for your Assateague Island Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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 86+ Rentals in West Ocean CityPiney 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 29+ Rentals in Piney IslandBest 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
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
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
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
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
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.
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.
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 Lighthouse
Chincoteague National Wildlife Refuge
Assateague Point
Assateague State Park
Assateague Island National Seashore
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.
Frequently Asked Questions About Assateague Island?
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:
- PET-FRIENDLY! Just Steps To Famous Chincoteague Pony Penning & Carnival Grounds
- Waterfront 5 star: Ponies! SAVE! Off season Rates starting at 250.00
- Featured DC magazine 10 BEST/Waterview CLOSEST community to BEACHn3 decks.
- Elegant Waterfront Residence, Magnificant Sunsets, Close to Town Ctr, Elevator
- Cozy island cottage with a Key West flair - CLOSEST TO THE BEACH!
- Chincoteague Island Getaway
- Josie's Getaway - Pet Friendly -Mini-Vacations and Month to Monthly Available
- Snow Hill Riverfront Retreat : Wildlife, Fishing, Kayaking, Nearby Beaches.
- Sunset Bay Villas 'Another Day in Paradise' Amazing Water Views & Sunsets
- Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
2. How many vacation rentals have private pools in Assateague Island?
There are 41 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 2026 is over 1173 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
House
10.0(239 Reviews)
3 Bedrooms
2 Baths
6 Guests
1900 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
R5,109/Night
7 Nights - R35,761
Condo
10.0(112 Reviews)
3 Bedrooms
2 Baths
8 Guests
1979 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
R11,562/Night
7 Nights - R80,932
Condo
10.0(72 Reviews)
3 Bedrooms
2 Baths
8 Guests
1800 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
R7,144/Night
7 Nights - R50,000
Condo
10.0(67 Reviews)
3 Bedrooms
2 Baths
9 Guests
1800 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
R7,337/Night
7 Nights - R51,351
Condo
10.0(51 Reviews)
3 Bedrooms
2 Baths
8 Guests
1800 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R7,185/Night
7 Nights - R50,296
House
10.0(30 Reviews)
2 Bedrooms
2 Baths
5 Guests
1500 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R3,908/Night
7 Nights - R27,356
House
10.0(25 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
R4,147/Night
7 Nights - R29,021
House
10.0(13 Reviews)
3 Bedrooms
2 Baths
8 Guests
1556 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
R5,000/Night
7 Nights - R35,003
