Holiday rentals in Winchester

WildernessTrace BarrelProof *Hottub/firepit*

Whether you’re here for Centre College, the Bourbon Trail, or romantic getaway, you’ll find this 2 bedroom bungalow exceeds expectations. This home is conveniently located 2 1/2 blocks from Main St. so you can enjoy a nice walk to dinner to one of Danvilles restaurants. The home features a bourbon theme throughout with knick knacks from “The Mandalorian.” From barrel barrel head tables, staves, bourbon bottle lamps, and other bourbon distillery keepsakes, this house is first class throughout.

Brand New! The Mighty Acorn, Bungalow at the Gorge

Come retreat to this charming cabin nestled in the woods. Surrounded by cliff walls and lush greenery, this private oasis offers a peaceful and serene escape from everyday stress. Step inside to find 2 queen bedrooms, a kid's loft with 2 twin beds, and stocked kitchen. Whether you're snuggled up by the firepit, soaking in the hot tub or enjoying breakfast on the deck, every corner of this home exudes warmth and comfort. This is a true sanctuary where you can unwind, recharge, and reconnect.

Shine On near Red River Gorge!

A cozy little getaway located at the entrance of Indian Creek Resort!! Keep it simple at this peaceful and centrally-located place. Amazing cabin located near Red River Gorge, Daniel Boone National Forest and Cave Run Lake. A Private Backwoods wonderland!! A short scenic drive(20-40 minutes) to everything the area has to offer. Centrally located between Kentucky's most desirable hiking trails. Forget your worries on the spacious back deck, relax and unwind in the hot tub. 1bed/1bath

Smallwood Cabin-RRG-LUX-hot tub | wifi

Welcome to Smallwood Cabin! Exquisite attention to detail and quality abounds! Newly built in the heart of all the Gorge has to offer. Luxury linens, rugs, and decor set this place apart from others. Fully custom bathrooms with unique fixtures, walk in shower, and onsite laundry make your stay comfortable. Reminisce around the outdoor fire pit overlooking a tranquil pond or in the private hot tub! Easy check in, last min booking, & close to nature make the whole experience refreshing!

Jaw Dropping Getaway in the Heart of RRG!

Discover the one-of-a-kind Manor House, nestled in the heart of Red River Gorge's Cliffview Resort, and positioned directly beneath the awe-inspiring Milky Way. Aptly known as the "Island in the Sky," this iconic residence at Cliffview rests at the tip of a picturesque point, surrounded by towering rock cliffs and pristine woodlands below, with the stars twinkling above. With 5 bedrooms, 3 bathrooms, and accommodations for 16 guests, this cabin is ideal for gatherings on any occasion!

Klyfta Haus 4Br Lakeview HotTub FirePit EV Charger

Welcome to Klyfta Haus! Perched on a serene 1-acre hillside with breathtaking lake views. This modern 4-bedroom 3-bath log cabin offers a hot tub, fire pit, EV charger, games, shuffleboard, and ample parking. Unwind while taking in the sleek, rustic interior, or savoring the views from the deck, it’s the ultimate blend of adventure and relaxation. Conveniently located near all the Red River Gorge attractions, it’s perfect for a romantic escape, family getaway, or group adventure.

Wishing Well Guesthouse On The Lake

A peaceful, waterfront guesthouse in a serene quiet neighborhood. On 2 acres of rolling hills, this choice location will be a peaceful getaway. Updated furnishings and appliances in this beautiful, open concept living space with a gas fireplace inside or a rustic fire pit outside. Close to lake marina rentals. #Center College #Pioneer Playhouse #Brass Band Festival #Pasture at Marksbury Farm #KY BBQ Festival #Bourbon Trail #Norton Center For The Arts #127 yard sale

Traveler's Cottage

Beautiful Craftsman style Bungalow in the heart of Berea. This two bedroom, two bath cottage has off street parking and is a short walk to Artisan Village/Old Town, galleries, shoppes, and cafes. Step into a beautiful, comfortable, clean environment featuring original art, hardwood floors, tall ceilings, queen sized beds. Basic TV channels, Roku, and High Speed Internet. Walk to Nightjar dinner, Native Bagel for breakfast or an early lunch. Great neighborhood!

Briar Patch Cabin-RRG | Fire Pit | Sunset | Wi-Fi

Located along the outskirts of the Red River Gorge Scenic Byway, The Briar Patch is perfectly situated to host travelers who are seeking both privacy and convenience. This cabin was thoughtfully designed to host anywhere from 1 to 6 people without making guests feel too cramped or in a space that’s too large to feel comfortable. Its rustic interior creates the perfect mood for this dreamy mountaintop vacation home.