'Loophole' + Oceanfront + Historic Cottage + Nags Head NC - Vacation rental home in Nags Head, NC

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 gorgeous 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. Savor your stay worry-complimentary! Let us know if you have any questions.