Assateague Island Winter Rental
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $434/Night
For 7 Nights US $3,040
1603.82 ft²
5 Guests
2 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Parking
- Internet
US $201/Night
For 7 Nights US $1,407
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Pool
US $352/Night
For 7 Nights US $2,463
2200 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $381/Night
For 7 Nights US $2,664
1797.57 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Parking
- Air Conditioner
US $153/Night
For 7 Nights US $1,070
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $268/Night
For 7 Nights US $1,876
1797.57 ft²
6 Guests
1 Bedroom
3 Bathrooms
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $325/Night
For 7 Nights US $2,273
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $212/Night
For 7 Nights US $1,483
7 Guests
1 Bedroom
2 Bathrooms
Free Cancellation
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $396/Night
For 7 Nights US $2,769
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
US $380/Night
For 7 Nights US $2,657
8 Guests
4 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $390/Night
For 7 Nights US $2,728
1500 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
US $237/Night
For 7 Nights US $1,660
Why Choose Rent By Owner for your Assateague Island Winter Rental?
What makes our Winter Rental 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.
Weekly Weather Forecast for Assateague Island
How to Book Your Assateague Island Winter Rental
What's our booking process?
Our platform allows you to browse a curated selection of winter rental. 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 Winter Rental Amenities
What amenities can you expect?
Our Winter Rental 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
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 Winter Rental Frequently Asked Questions
1. What are the top Winter 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 Winter 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
- Snow Hill Riverfront Retreat : Wildlife, Fishing, Kayaking, Nearby Beaches.
- Sunset Bay Villas 'Another Day in Paradise' Amazing Water Views & Sunsets
- STUNNING WATERFRONT VIEWS!
- Sunset Bay Villas - 'Sunset in Paradise' Amazing Water Views & Sunsets
- Island Pony - Outstanding 3 BR W/F Duplex/community pool NO LINENS
- Hot Tub Haven 2 Mi to Beach! ‘Christy's Cottage’
2. How many Winter Rentals are available in Assateague Island?
Currently, the total number of properties listed by RBO in 2026 is over 495 in the Assateague Island area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Assateague Island.
More Rentals You May Like Near Assateague Island
2454.17 ft²
7 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Parking
US $460/Night
For 7 Nights US $3,218
6 Guests
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- Oceanfront
- Fireplace/Heating
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700 ft²
6 Guests
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1 Bathroom
Ocean View
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1200 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
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US $211/Night
For 7 Nights US $1,474
6 Guests
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Ocean View
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- Balcony/Terrace
US $277/Night
For 7 Nights US $1,937
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
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- Fireplace/Heating
- Balcony/Terrace
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US $373/Night
For 7 Nights US $2,614
1600 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $181/Night
For 7 Nights US $1,267
8 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $351/Night
For 7 Nights US $2,458
1100 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $214/Night
For 7 Nights US $1,498
1800 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $378/Night
For 7 Nights US $2,645
6 Guests
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House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $229/Night
For 7 Nights US $1,603
6 Guests
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2 Bathrooms
Family Friendly
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- Fireplace/Heating
- Balcony/Terrace
- Kitchen
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