Pet-friendly holiday rentals in Letcher County

Tranquility in the Mountains - House

Peaceful getaway offers relaxation & adventure in the KY mountains. Short drive to VA & TN. Large home has 4 bedrooms - 2 w/ private bath & 2 that share a double-vanity bath. Open living/dining area and kitchen. Nearby is a 7-hole golf course and swimming pool (available Memorial Day - Labor Day), hiking, and tourist attractions such as Portal 31 and the KY Coalmine Museum, as well as Kingdom Come State Park. Plenty of parking; can accommodate trailers & RVs. RV park is a 45-minute drive.

Dan’s Den - Two bedroom home with outdoor firepit

Welcome to Dan’s Den, a spacious two bedroom home in the heart of the Appalachian mountains. Centrally located in Cumberland, the black bear capital of Kentucky. You’ll find many of the luxuries of a fine home here, but in a smaller home more suitable for a solo traveler, a couple, or small family. Enjoy two large living rooms, one of which is the newly added “log room”, cozied up in front of the fireplace for games, movies, or just to relax with a good book and a hot cup of coffee.

Big Tree Lodge- Near Leatherwood Off Road Park!

Mountain Getaway with Direct Trail Access | Pet-Friendly, Sleeps 10+ Escape to the mountains of Eastern Kentucky in this spacious 4-bedroom, 2-bath home located in peaceful Slemp, KY — just minutes away from the trails at Leatherwood Off-Road Park! Whether you're hitting the trails or looking to relax, this home offers the perfect base for adventure and comfort. Parking trucks with large trailers is not possible. Only one small trailer so please see the pics before booking.

Whitesburg Vacation Home w/ Screened Porch

Your next adventure awaits at this Whitesburg vacation rental near the North Fork Kentucky River! This 3-bedroom, 2-bathroom home offers an updated interior and features stainless steel appliances, an in-unit washer and dryer, a laptop-friendly workspace, and more. Spend the day exploring the Bad Branch State Nature Preserve, walk to the Letcher County Recreational Center for countless activities, or opt to stay in to watch a Netflix movie or show on the Smart TV!

Ritchie Homeplace - A National Historic Site

This home has been designated as a National Historic Site & a Kentucky Heritage Home in honor of the work done by Jean Ritchie in the preserving the musical heritage of the region. It offers 6 bedrooms, 1.5 baths, dining room, kitchen, multiple outdoor seating areas & plenty of parking. This home was full of love, laughter, music and family traditions and we hope you discover this for yourself during your visit! And, pets are welcome too!

The Hillbilly Hideout

Tucked in the trees and just minutes from the Hillbilly Trail System, this modern cabin is your go-to basecamp for off-road adventure and mountain downtime. Whether you’re here to ride, relax, or both—you’ll have all the comforts of home without losin’ that good ol’ backwoods feel. With room for up to 6 guests, a full kitchen, fire pit, and plenty of space for your trailer and SxS. We have two neighboring cabins for larger groups.

Dandelion Bungalow

This special place is close to downtown Whitesburg and right across from the entrance of Tanglewood Trail. It is within walking distance of Kentucky Mist, a few local restaurants, a recreational center, the farmer’s market, and Cane Kitchen. We are located at the foot of the scenic Pine Mountain and a short drive to hiking trails, overlooks, and other attractions.

Bed and Biscuit Inn Pets are family too!

Enjoy a memorable visit when you stay in this unique place. This home is decorated and set up to accommodate you and your pet family. Located off U.S.119 between Kingdom Come State Park and Bad Branch Falls. It’s also the perfect location for family reunions. The old rustic store is beside of it and available to rent on Airbnb.

The Cozy Corner

This home is ideally located just minutes from downtown Whitesburg, within walking distance to Main Street and the Tanglewood bike and walking Trail. Recently remodeled, it features a fully stocked kitchen and dining area, as well as a spacious backyard. There is ample street and carport parking for up to 2 cars.