Vacation rentals with outdoor seating in Georgetown

Man O'War @ The HoM- KY Horse Park, Ark, Historic

Welcome to Man O War! A 1500 sq ft luxury 1st floor condo located inside the Historic House on Main. This 2-bedroom, 2 bath condo offers a perfect blend of modern luxury & style coupled with the elegant charm of a Historic Kentucky home. Originally built in 1872, The House on Main functions as a charming boutique hotel property with 4 units: Secretariat - 1st floor 2bed/2ba Man O’ War - 1st floor 2bed/2ba Sir Barton - 2nd floor 1bed/1ba (w/sleeper) War Admiral - 2nd floor 1bed/1ba (w/sleeper)

Cozy, cute 2BR townhouse near downtown, businesses

Registration#15019537-1 Comfy, cozy Five Squared is tucked in a quiet neighborhood near downtown's restaurants, bars and arts; Rupp Arena and UK basketball games and concerts; the hip Distillery District's restaurants; and Meadowthorpe's antique shops. For business travelers, it's also convenient to New Circle Road and local industry. Our place is great for couples, solo travelers, families with kids, and anyone who likes cotton sheets, exposed brick and the gentle rumble of passing trains.

KY & Bourbon & Horses, Oh My! Close to Keeneland

This home has been completely renovated with flawless finishes and top of the line appliances. This is for the UPSTAIRS only. (No one else lives at the residence & is solely for Airbnb) 10 minutes from Keeneland & a few miles from hospitals. Convenient location to shopping and restaurants. Clean and comfortable living spaces. This is a chefs kitchen, that has double doors to a walk out patio. The bathroom has a Bluetooth fan. I’ve provided everything to make your trip enjoyable as possible.

Distillery District Diamond-pet friendly

This 1948 bungalow in an up-and-coming neighborhood has two bedrooms/one bath. This house has all the updates you could ask of modern living including internet access, TVs with Roku, and keyless entry. Each bedroom has blackout curtains, ceiling fan and bedside power station. The bath is fully stocked with essential personal care items. The fenced-in back yard has a deck and a fire pit. STR Reg #15075605-1. Maximum occupants 4-Guests are prohibited from allowing more than maximum occupancy

Buffalo Springs Distilling Company

It’s recently been brought to our attention about Airbnb scams! Please reserve with us or someone else that has a history! The Bourbon Trail The Buffalo Springs Distilling Company got it's start in 1868. It closed and it's warehouses were emptied out by the 1970's. This building is one of the last structures left on the site. This historic building was the main office and gatehouse for visitors to the distillery, so we can offer one Queen sized bedroom due to the size of the structure.

*Unique Country Cabin *1BR 20 min from The Ark!

No neighbors! It’s not a big or fancy place but it’s clean, simple, and relaxing. The stars are brightest in the country when enjoying the fire pit. Our two story cabin has 1BR with two double beds, full kitchen, full bathroom, recliners, and grills. It's perfect for couples, friends, or small families. The Ark Encounter, Kentucky Horse Park, Keeneland, and several distilleries are all within an hour of the cabin. This is a great place to relax between visits to these attractions.

★Escape & Relax ~ Breathtaking Creekside Getaway★

Escape the everyday hustle and bustle by immersing in the stunning glamping experience on a secluded creekside property. Enjoy solitude, romance or family time inspired by nature. Tucked away on our 13 acre residence, this spacious 16' tent offers a unique stay in a breathtaking ambiance. ✔ Queen Bed + 2 Full-Size Mattresses ✔ Outdoor Deck with Seating ✔ Bathtub + Separate Shower ✔ Composting Toilet ✔ Creek Access + Kayaks ✔ Cooking Station Learn more about this glamping haven below!

Carriage House on the Park

Enjoy the tranquility of this Upstairs Apartment (over 400 sq ft) suite, located across from Winchester's College Park. Executive amenities include heated bathroom floor tile, additional sink and vanity and large flat screen Roku Smart TV. Carriage house is located just steps from public gym and recreational center and historic downtown Winchester. Centrally located with easy access to Lexington, Paris, Versailles, Georgetown, Kentucky Horse Park, Natural Bridge and Red River Gorge.

Creekside Kentucky Cottage

2 bedroom, 1 bathroom creek side cottage located minutes away from many attractions. Whether you are in town for a bourbon tour or two, to visit your kids at college, or a stroll along horse country, Central Kentucky does not disappoint! Located on Elkhorn creek, enjoy fishing and wildlife with creek side living. Across the creek there is a walking trail that leads to a dog park. Watch kayakers and boaters launch across the creek from you, or bring your own and join in!

Sleeps 8. Cozy Bungalow in Downtown Georgetown

Brand new, 4-bedroom home minutes from I-75, this is a central location to all things Ky has to offer! 15 mins to Ky Horse Park. 30 mins to ARK & Bourbon Trail. Our guests will enjoy comfy beds, luxury bedding, a pack & play, a well-stocked kitchen w/ granite countertops & stainless appliances, Smart TVs in every bedroom, high-speed wifi, 2 full baths, laundry, off-street parking, a deck & spacious backyard w/ charcoal grill & firepit.

Uptown Retreat- Fireplace, Sauna -Romantic Getaway

Welcome to Uptown Retreat, a cozy Lexington hideaway perfect for couples, solo travelers, and business guests. Relax by the fireplace or in your private sauna, cook in the efficient kitchenette, or enjoy the covered patio with Adirondack chairs. With fast Wi‑Fi, Smart TV, and a dedicated workspace, this stylish, comfortable retreat blends relaxation, convenience, and premium location in one guest-favorite space.

Horse Central-Be our Guest!

Comfortable, easily accessible home! Convenience at it's best! Only 5 minutes to the Kentucky Horse Park, 10 minutes to Keeneland or Fasig-Tipton, 1 mile to Kearney Creek Golf Course, 10 minutes to downtown Lexington and Rupp Arena. 15 minutes to Georgetown. Easy access to the Bourbon Trail and beautiful drives past many famous horse farms as well as access to I-64 and I-75.