Vacation rentals in Pippa Passes

Small Town Charmer - Hazards Best Airbnb!

This lovely cottage style home is located in a well established neighborhood in downtown Hazard. It is perfect for guests coming into town for work, family gatherings or a weekend away. The home will comfortably sleep up to 7 guests & pets are welcome too! This location is 10 minutes to ARH, 5 minutes to HCTC, & surrounded by areas for hunting, fishing & trail riding. The home is also located within an hours drive to the Red River Gorge, several lakes, ATV parks, mountain bike & hiking trails.

Cozy 3-BR 2-bath cottage near highest point in KY

Nestled in the heart of Lynch, KY, surrounded by comforting mountains, sets the Mountain Escape Cottage. Less than 1 mile from Portal 31, you can dive deep into the rich history of this tiny coal town. Within minutes you can drive to ATV parks, the highest point in KY, and many other mountainous adventures. Grab some coffee at the old cafe turned coffee shop, and visit the KY Coal Museum just 5 minutes away in Benham, KY. You and your family will leave here with beautiful mountain memories!

Hideaway in the Holler

Come make memories that will last a lifetime at our Hideaway in the Holler. Our cozy but airy cabin offers leather reclining couch and love seat, full kitchen, two bedrooms with queen beds, full bath with walk in shower, and laundry facilities. Hi-speed internet and a dedicated desk space make working remotely a breeze. Enjoy the big screen tv with all the streaming apps or get back to nature relaxing by the wood burning fire pit or on the wrap around porch overlooking our beautiful creek.

Bee Still Tiny Home, Graham Estates, LLC

Take a step into our dreamy tiny home when the world is telling you to find a place to "bee still." The perfect destination for a romantic getaway, or a family vacation where the kids can make a fort in the loft. You will love this quiet, serene space located up a scenic driveway. The porch overlooks a small pond, and across the road you will find our small farm of goats and piggies. Take a walk around the property or enjoy all the adventures awaiting at Red River Gorge 35 minutes away.

The Shotgun House

Enjoy your stay at the Shotgun house located in the heart of Prestonsburg within walking distance to a popular restaurant and downtown shopping. This cozy house offers a 58" TV and playstation in the living and also a 50" TV in the bedroom. Relax outside on a covered porch and enjoy the occasional local live music. Located close to the Prestonsburg Passage Trail, Mountain Arts Center, Middle Creek National Battlefield, Pikeville Exp Center and a short drive to the Red River Gorge.

The Stone Studio

A historic two-room studio cottage built from Kentucky River rock. Entire cottage rented for your privacy. Recently renovated with the modern conveniences of a kitchenette, outdoor smoking area, Wi-Fi, RokuTV, and blackout curtains. High ceilings create a bright and spacious feel. Conveniently located close to downtown. Off street parking by your front door. Walk to Main Street, Appalshop, and Kentucky Mist Distillery as well as many other small businesses and restaurants

Sweet Dreams

* If you book for 7 days or more, you will receive a 20% discount off your stay. If you’re in town on business, to visit family or just traveling through, this 2ND FLOOR APT is perfect for you. Enjoy a full kitchen & onsite laundry facility. You’ll get a good nights sleep in a quiet space, on high quality mattresses. We are conveniently located just down the street from a Food City. We have a work desk & free WIFI. We’re just a 5 minute drive from downtown Pikeville.

Cowan Creek Cottage

Cowan Creek Cottage is close to the Cowan Community Center and only 5½ miles outside the city limits of Whitesburg. The cottage is located at the foothills of Pine Mountain. You’ll love the cottage and enjoy the feel of having your own little home in the mountains. Enjoy a clean and comfortable home away from home while visiting friends and family and enjoying our community. Cowan Creek Cottage is good for couples, solo adventurers, business travelers, and families.

Private 12 Acre Escape - Hot Tub, Firepit, Arcade

12 acres of peace and quiet in Campton. You can wander the trails, kick back by the firepit, or just take in the forest views. Evenings are for porch sunsets, hot tub stargazing, and the sound of birds all around. Inside, there’s a vintage Ms. Pac-Man for a little throwback fun. We’re about 15 miles from Red River Gorge, but it feels like you’ve got the whole place to yourself—no close neighbors, no traffic, just dark skies and starry nights.

The Potting Shed

This unique space is so charming you may never want to leave! Newly renovated with all the conveniences of home! A comfortable living space, fully stocked kitchen, free Wi-Fi and cable TV, beautiful outdoor patio space, outdoor grill and several items available for you to borrow for the perfect hike or picnic! It's the perfect spot for exploring Whitesburg and Letcher County. We know you will absolutely love your home away from home!

Bear Creek Cabin • Vineyard Views & Fishing Pond

Escape to Bear Creek Cabin, overlooking the pond on MountainRose Vineyards. Enjoy peaceful porch views, modern comfort, and easy access to winery tastings, mountain trails, and quiet evenings under the stars. Perfect for couples or solo travelers seeking a serene getaway. Fishing is allowed in the adjacent pond with waiver signature. Must bring your own fishing equipment.

The Burg

Enjoy local venues, The MAC, Planetarium, Jenny Wiley Lake, 1620 Distilling Company, hiking, biking, wildlife, local artisans and crafts. Home to Loretta Lynn's, Butcher Holler. Civil War History. Close to downtown shopping, walking distance to dining, coffee shops, and bakery. There are 2 rather short flights of stairs to access this unit.