About this Property

Sleeps 9
4 Bedrooms
2 Bathrooms
Cottage

Oceanfront Historic Cottage on Nags Head's iconic Cottage Row! Located in the dunes, The Loophole blends timeless appeal + modern amenities. This 4-bedroom, 2-bath gem is steeped in history, featuring original architecture and rich family memories. Wake up to striking ocean vistas, walk the beach, or discover Jockey’s Ridge just steps away. Feel the magic of the Outer Banks in a one-of-a-kind getaway where history meets luxury. Book now and create your memorable story!

Located among the storied dunes of Nags Head’s Historic Row, The Loophole is a one-of-a-kind oceanfront bungalow steeped in Outer Banks history and charm. This timeless home preserves the original architecture that has made Historic Row a beacon of the past—showcasing pine tongue-and-groove walls reminiscent of materials salvaged from old shipping vessels that once braved the seas to deliver supplies to these remote barrier islands.

Lovingly cared for by one of the first families to call the Outer Banks home, The Loophole has served as a cherished gathering place for generations. Photographs, keepsakes, and thoughtful details throughout the home tell a story of countless summers spent by the shore. Now, this treasure is shared with you—a rare opportunity to experience the heart and soul of Nags Head in a space filled with warmth, character, and history.

Neighborhood + Conveniences

>>Coffee Stores + Cafés
Morning View Coffee House – 0.6 miles
Waveriders Coffee, Deli & Market – 1.0 mile
Front Porch Café – 1.2 miles
Sea Level Coffee & Kitchen – 1.4 miles

>>Grocery Stores
Food Lion – 1.1 miles
The Fresh Market – 1.5 miles
Publix – 3.0 miles

>>Ice Cream + Treats
Surfin' Spoon – 0.7 miles
Sweet Retreat Ice Cream Parlor – 1.0 mile
Fat Boyz Ice Cream – 1.2 miles

>>Eateries
Blue Moon Beach Grille – 1.1 miles
Miller's Waterfront Restaurant – 1.3 miles
Tortugas' Lie – 1.5 miles
Lucky 12 Tavern – 1.6 miles
Sugar Creek Seafood Restaurant – 2.0 miles

>>Shopping
Outlets Nags Head – 2.5 miles
Seagreen Gallery – 1.2 miles
Cavalier Surf Shop – 0.9 miles
Life on a Sandbar – 1.3 miles

>>Adventure + Activities
Jockey's Ridge State Park – 0.5 miles
Jennette's Pier – 2.2 miles
First Flight Adventure Park – 2.5 miles
Causeway Watersports – 2.7 miles

**Minimum Age Requirement is 25 years old**

Waivo Damage Protection – Peace of Mind for Your Stay
Instead of a security deposit, we’ve added a non-returnable $75 Waivo Damage Protection Fee under the Management Fee. This covers minor accidental damages, so you won’t be charged for modest mishaps like spills or broken items. For damages over $3,000, we will work with the guest to resolve the issue, including legal action if necessary. Appreciate your stay worry-complimentary! Let us know if you have any questions.

About the Area

Nags Head is home to this property. Outer Banks Beaches and Jockey's Ridge State Park reflect the area's natural beauty and area attractions include Full Throttle Speedway and Mutiny Bay Adventure Golf. Destination Fun and Stop-N-Shop Beach Shop are also worth visiting.

Special Instructions

Extra-person charges may apply and vary depending on property policy

Pet Policy

Pets not allowed

Nags Head vacation rental tips:

Sticking to your rental budget:

Booking your Nags Head vacation rental in Fall or Spring months is our favorite way to save money on your vacation home. Rental rates are lower, and you'll find a larger selection of desirable properties. Many vacationers use this method to find larger homes within budget, or to reserve an oceanfront rental that would otherwise be unavailable during the high season. Speaking of the off-season, don't overlook Winter holidays for a Nags Head vacation! Who wouldn't love a holiday on the coast? Thanksgiving, Christmas, and New Years are great times to gather with family and friends at your favorite beach.
The sooner you can book, the easier your search will be. The best vacation homes are reserved very early. Reserving your vacation rental six - twelve months before your travel dates is recommended. Holidays such as Christmas and Thanksgiving are excellent times to plan and reserve your vacation home.
Some owners offer discounts for veterans and active duty military. Remember to ask your host or property manager if discounts are available for your group.
Property management companies usually offer their guests an option to purchase trip insurance protection. Trip insurance, which normally will cost you 1% - 5% of the base stay price, offers visitors reimbursement of their vacation costs for any missed time as a result of medical-related catastrophes or weather disasters, as well as ensuing additional evacuation charges, such as an unanticipated hotel stay or extra gasoline expenses. Trip insurance might be a a life-saver if the unforeseen occurs. Ask your host for program terms and fees.
Find a copy of your local visitors guide when you arrive at the rental property. If your rental property doesn't have one, you can find them at local shops and visitor centers. In addition to great local information, travel guide magazines have deals for local tours and attractions.

How to choose the best rental home:

Choose your vacation dates and maximum budget.
Decide how many bedrooms and the configuration your group needs. 'Loophole' + Oceanfront + Historic Cottage + Nags Head NC has 4 bedrooms and 2 bathrooms. If you need a larger or smaller rental, use our rentals search.
Precise descriptions of bedrooms and bed counts & types is usually available on booking websites. If they are not listed, email or call the property manager before you reserve the vacation property. Remember that most properties list the max. guest capacity, which usually includes pull out couches in living rooms.
If there's a certain Nags Head beach you are crazy about, look for rentals that are either near by, or those that cater to your requirements.
Appropriate accessibility amenities can make or ruin a vacation for persons with disabilities. Make certain to inquire about specialized equipment and wheel chair accessibility.
Traveling with pets? Although a number of vacation homes allow pets or animals, guidelines and costs vary per property. Allowable pet type, breed, and size are often limited. Remember to ask the property manager before booking, and study your agreement! Pet fees or charges could be applied to your invoice.

More tips for your visit:

Take a copy of the owner's contact number and check in/check out procedures for your rental. We recommend storing the host's contact information in your smartphone and wallet.
To make certain that damages are not attributed to your family's visit, make a record of any problem areas upon check in. text the rental manager right away to document any issues. If there is a dispute about who is responsible, having a record of concerns and contact attempts will be helpful.
Property managers are there to help! Feel free to ask any questions during your stay.
Respecting late-night quiet hours and parking regulations can make a stay significantly more pleasurable. Be a good neighbor. You'll magnify your chance to make some new local friends, and resident neighbors can be an incredible source for finding the best local restaurants, beaches, and hangouts.
Speaking of neighbors... Ask a local resident! Neighbors can often help you find exactly what you're looking for. Who better to ask where to find the best seashells, have a great night on the town, or the best spots for bird watching?
Lock your vacation home while you're away. Protect the owner's property and your things!
When it's time to leave, take a final walk-through to confirm you haven't forget anything. Make sure to check bathrooms, garages, and back yards for hidden belongings. Remove everything from the refrigerator and take any leftovers home.
Please make sure to walk through the property one final time and scan for damages to contents or the property itself. We suggest inspecting the property with the host whenever possible. If the host isn't available, ensure that you take video of the property to record its condition.
Remember to leave feedback! Property owners rely on great feedback to stimulate future reservations. They'll be grateful for your review. Alternatively, if something went wrong, other families will appreciate that you share your experience find their best vacation home. Remember to be objective. If something fell short of expectations, consider whether the host had any control over the issue, and if so, whether they responded expeditiously to solve it.