Family-friendly holiday rentals in Cashiers

Historic Luxury Cabin | Private Outdoor Tub

Heady Mountain Cabin, a restored 1890 retreat with outdoor claw foot tub, nestled between the Nantahala National Forest and our horse pasture. Curated for a luxurious stay with rustic charm, spa-level comfort, and space for romance and reflection. Breathe fresh air, soak in the private outdoor tub, play a record, gather by the firepit. Slow down and reconnect with yourself, each other, and nature. Fresh coffee and a welcome drink await. Ideal for a romantic escape, solo retreat, or small family.

Live-In Art Gallery | Walk to Main | Steps to BBQ

Welcome to Art Chalet "Art in the HeART of Highlands". Enjoy a live-in ART GALLERY where fine-art fills every room, and every piece is for sale, set against breathtaking mountain views and natural light. Nestled on a lush hillside with two outdoor fireplaces, this chic walk-to-town mountain retreat blends elevated design with an unbeatable location~ 1 minute drive to downtown & steps to Smokehouse BBQ & High Country Wine Shop. Perfect for romantic getaways, couples retreats, & girls weekends.

Luxury Log Cabin • Hot Tub • 7 min to Highlands

Retreat to the silent woods in meticulously restored original “Joe Webb” log cabins: Gilmer Lodge marries the nostalgia of original rustic period architecture with modern finishes, including completely new kitchen and bathrooms. Nestled beneath old-growth tree canopy, this design-forward property includes two separate log cabins – circa 1790 and early 1900s – that together function as a single home. The two cabins are adjacent to each other, connected exteriorly by a wrap-around covered porch.

Magical Wizarding House Near Top Attractions!

Experience the magic of the wizarding world in our enchanting house! Nestled on the Mountain Shire property (check out our insta @mountainshire), just minutes from Pigeon Forge, Smoky Mountains National Park, and Dollywood. Relive your favorite scenes with magical decor inspired by your favorite books and movies. Sleeps 6 with a queen loft bed, sofa bed, single bed in a nook, and bed under the stairs. Enjoy Roku TVs, a kitchenette, and a patio with chiminea. Perfect for a magical getaway!

Hide Inn Seek Hillside Treehouse 1.5mi to Main St

Escape to luxury at the Hillside Treehouse brought to you by the biophilic hospitality brand 'Hide Inn Seek'. Located in Highlands NC, just 1.5 miles from main street, this newly built home sits boldly among the trees allowing you to indulge in nature while enjoying luxury accommodations. The 58 step ascent leads you up to a treehouse experience like no other. Check out our newly listed sister property, Bird Nest Treehouse, designed just for couples—complete with a full spa experience!

Huge Views, Outdoor Tub, Fire Pit, Close to Town!

Perched at 4,200' high and under 10 minutes to downtown Highlands and Cashiers, this easily accessed, light filled, cabin offers massive, year-round, long range views of Whiteside &Rock Mountains from every room of the house as well as from our expansive decks! -10 Minutes to Downtown Highlands (shopping, dining, art culture) -8 Minutes to Cashiers Crossroads (Whiteside brewery, coffee, shopping) -5 Minutes to Whiteside Mountain trailhead -15 Minutes to Lake Glenville (Boat Rentals!)

Mountain Gem Breeze Hot Tub and $1M Views

Perfect spot to get engaged! 13 proposals in 2025!!! Did someone mention endless million-dollar views! Perfect place to pop the question and we can help with extra decorations! Enjoy a stylish experience at this centrally located place. Mountain Gem Breeze @ Whiteside Cliffs is located inside a gated community. The hiking possibilities are endless! A short trip to downtown Cashiers or Highlands makes this central location a dream come true. Less than 5 minutes to Cashiers Sliding Rock!

Luxurious Geo Dome 2 king beds 6 guest hot tub

Luxurious Geo Dome Retreat just 25 min from Asheville This spacious dome features a huge window with breathtaking views of the tree tops and distant mountains from 3000 feet. Perfect for up to 6 guests: 2 king beds and 2 off-the-floor chairbeds. The dome has a fully equipped kitchen, soaking tub, shower, hot tub, fire table, grill, 65"TV, dining table and chairs for 6. A state-paved road leads directly to the front steps. Experience the ultimate glamping getaway in this unique oasis.

Bright & cheery! Modern, quiet, peaceful.

Discover a bright mid-century inspired cabin nestled on 4+ private acres near Cashiers & Highlands, NC. Thoughtfully designed with clean lines, natural light, and positive vibes, this stylish retreat features a screened-in covered porch, fire pit, gas grill, and a spacious deck for lounging or stargazing. Surrounded by nature yet close to town (20 minutes drive), it’s the perfect blend of mid-mod design, comfort, and mountain seclusion. Book your unforgettable escape today!

Incredible Mountain Views sitting on covered deck

Enjoy Waggly Butts & Bears Cabin, a recently renovated, completely private cabin that's incredibly quiet, overlooking Black Mountain. You'll have your choice of many outdoor spaces, including a large, covered deck w/heaters & fire table, uncovered deck w/Adirondack chairs, outdoor eating area, a covered porch & a separate tin-roof deck for grilling or laying on the full-sized swing bed. The fire pit area has 6 Adirondack chairs in the natural woods setting. Dogs welcome!

2BR Mtn Top View • Hot Tub • Cashiers & Highlands

Mountain top retreat nestled at 4000ft elevation. Between the Blue Ridge Mountains and a Christmas tree farm. Enjoy expansive views in this secluded home away from home. Located in Glenville, NC just 17 minutes to Cashiers and 33 minutes to Highlands. This 2/2 is a perfect couples getaway or come enjoy it with some friends and family. This westward facing house will have you enjoying unmatched sunsets every night after a day full of exploring the area. @stayatstardust

Cozy bark covered cottage-spring/summer getaway?

Bark covered cottage in a lush mountain laurel forest, yet close to everything! Beautiful front porch, upscale furnishings and detailing, full kitchen, beautiful, subway tile walk in shower. The weather in Cashiers is ideal for hiking, biking, fly fishing, golf or just relaxing! We do ask three day bookings on weekends. Your dog is welcome - there is a $100 dog fee.