Four luxury rooftop vacation rentals

overlooking downtown Highlands,
North Carolina

Oak Over Main is an elevated rooftop retreat in the center of downtown Highlands. Our four luxury lofts are a brief stroll from Main Street, where you can enjoy an incredible dinner, an afternoon of shopping, or an evening of live music. At the end of your busy day, enjoy a glass of wine nestled by the heater on your private deck or step down to the rooftop garden, available only to our guests, where you’ll have a birds eye view of the action on Main Street.

241021 356 Main St Highlands Combine_Page_2

ELEVATED ACCOMMODATIONS

Our lofts’ earthy eclectic interiors were inspired by the surrounding Blue Ridge Mountains and the unique spirit of Highlands, NC. Each is outfitted with heated bathroom floors, private rooftop decks, Le Labo bath amenities, Nespresso coffee, full kitchens, and NetZero electric fireplaces. Whether you spend your days on the trails or in town, returning to your loft will feel like an extension of your adventure.

Overlook Loft

Summit Loft

Plateau Loft

Meadow Loft

Experiences Shared

" Oak Over Main is more than just a stay—it’s an experience. From the moment you arrive, you’re welcomed into a world of refined comfort and effortless elegance. The thoughtfully designed lofts, with their warm textures, heated bathroom floors, and NetZero fireplaces, create the perfect retreat after a day of exploring Highlands. It’s the kind of place where time slows down, where mornings start with espresso in a sunlit kitchen, and evenings end under the stars in the exclusive rooftop garden. A true sanctuary in the heart of Highlands—I can’t wait to return. "

— Emily R., Future Guest