Pet-friendly holiday rentals in Letcher County

Hibernation Station (trailer parking available)

This property is located near the entrance of Kingdom Come Start Park and right beside Stepp Fitness gym. It is also near local golf courses, Little Shepherd Trail, and the towns of Benham and Lynch. The Black Mountain ATV Park is only 15 miles away. The property has a master bedroom with a king bed, a second bedroom with a queen bed, and a 3rd bedroom with 2 twin beds. The master has an onsuite. It offers a washer and dryer, a full kitchen, and 2 water heaters to ensure hot showers.

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.

BROWN’S ELK CABIN

Brown’s elk cabin is an Authentic, rustic, log cabin. Located in the heart of the beautiful Appalachian mountains, overlooking the KY river, Only a short drive to Pine Mtn hiking trails, Bad Branch Falls, Little Shepherd Trail, Kingdom Come State Park, Raven Rock golf course, and only twenty minutes from the Va. state line. Perfect getaway for relaxing with family and friends, sitting by the fire pit, or exploring the areas natural beauty. Located 3 miles from Whitesburg

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!

Vicco Cottage Between Hazard and Whitesburg

Welcome to Vicco Cottage, a charming rental property perfectly situated between Hazard and Whitesburg, Kentucky. This delightful 2-bedroom, 1-bath cottage is designed for comfort and relaxation, making it an ideal getaway for families, friends, or couples looking to explore the beauty of Eastern Kentucky. Each bedroom furnished with luxurious king-sized beds. Only 4.6 miles from Carrs Fork Lake, a perfect spot for fishing, boating, and enjoying the great outdoors.

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.

John A. Webb historic building Apt A.

Welcome to the historic John A. Webb building, built in 1925, thoughtfully designed with original details including vintage lighting, built in bookcases, and original skylights dating back to the buildings construction! Apt A - The Harry Caudill apartment is a true time capsule and a retreat from all your worries!

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.