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2nd Story Historic Downtown 2 BR w Modern Comforts

Experience this unique and historic two bedroom apartment in the heart of downtown Winchester Kentucky. This building is over 150 years old and rich in history in the community, however, features modern amenities to ensure an amazing stay. This building is immediately across the street from the historic clocktower courthouse. You'll feel right at home in the fully remodeled bathroom (European Wet Room), kitchen and bedrooms. You'll also feel plenty of old world charm. Walking distance to all!

Cabin on I-75 in Lexington an Outdoor Destination

Rustic Cabin just off of I-75. Only 15 minutes from Lexington. Loft style with 2 futons, simple kitchen, and bathroom. A/C and Wood Stove. Spacious Front Porch. Towels and linens provided. Incredible views, abundant wildlife, access to Trails, Creek, Fishing thru nearby Outfitter. Pet Friendly with fee. Excellent stay over for travelers along I-75 needing some fresh air and nature! Gravel Driveway does require normal clearance, not for low riding vehicles. Adjacent parking lot available.

River Relaxation - Riverfront Home in Winchester

Kick back & relax in this calm, relaxing river front home. 3 king beds & 3 bathrooms! Beautiful deck and grill to take in the view. Several restaurants, beautiful hiking trials and a kayak rental all close by. This home is the perfect spot to unplug and spend time recharging. The home does have Starlink but NO or cable, but feel free to bring DVDs. T-Mobile- no service Verizon- no issues so far AT&T- Unsure *Due to it being a waterfront property there are neighbors close by

Hanna’s 1,400 SQ FT Downtown Royal Retreat Loft

1400 SQ.Ft in DT Winchester, KY. 1 bedroom 2 queen beds with 1.5 bathroom and laundry amenities . - experience luxurious living at an affordable price!!! -across the street from historical Courthouse -with Molder and Brand new furnishings and amenities to make this special aboard feel like home -Two Queen beds -two big TVs -Two new custom reclining couches, good for additional sleeping space -Private entrance+ample parking in the rear. Have fun at this unique and stylish place

Historic Cabin - Farm - Near RRG, Lex, local music

Join Laura, the founder of Laura's Lean Beef, Laura's Mercantile and Regeneration Distilling Co., at her farm at the edge of the bluegrass. The entire 1200 acres are open to guests, with easy access to the Red River Gorge, Winchester and Lexington. See farm animals and organic crops such as hemp, check out the aging barn for whiskey, while staying in an 18th century cabin updated with granite countertops, new beds and mattresses, modern bathrooms, and solar panels.

The Winchester Retreat

Welcome to the Winchester Retreat! We are located right off of I-64 in Winchester, just 30 minutes from both Lexington and the Red River Gorge. We're right down the street from Winchester's downtown, boasting restaurants, breweries, and shops. Pet friendly!! Come spend an evening by the fire pit and whip up a great dinner using our fully equipped kitchen or charcoal grill. We're also close to Legacy Grove Park, complete with a walking trail and dog park.

The River House Floor 2 Getaway, w/a river view.

Enjoy the spectacular views of the Kentucky River from this second floor studio. Located within an easy walk of hiking trails. After your hike (or whenever, you are on vacation), visit the Waterfront Grill or Hall’s on the River. They offer dining, bar, and seasonal outdoor seating. They are about a half mile down the road from the cottage. A tasting at the winery just a few minutes away will sweeten your stay. For more play, kayak rental is nearby.

College Park Getaway

Step into history with this charming home, blending classic character with modern comfort. Located just minutes from College Park, this spacious house offers cozy rooms, a fully equipped kitchen, welcoming living area and amazing outdoor space. Perfect for families or groups, enjoy the convenience of a historic neighborhood while being close to local attractions, including historic downtown Winchester, Red River Gorge, and charming cafes.

Scenic views, farm fun in peaceful modern cottage

A family-friendly farm that offers opportunities for couples, families or small groups to create special memories. Our farm is also the perfect place for unique family adventures, family reunions, retreats, parties of any type and intimate weddings - all in an idyllic country setting (events charged separately). We offer educational tours and introductions to our animals for guests that are interested.