Cottage holiday rentals in Shelbyville

River House - Cottage with KY River View & Access

Come relax at the peaceful river house. It feels like a retreat right on the Kentucky River with a party-sized dock for easy river access. It’s a cozy cottage on stilts with a breakfast bar on the porch and swing on the patio. Be surrounded by nature and beautiful views of the river and palisades. Tuck away in seclusion just minutes away from downtown Wilmore, Asbury University & Seminary. 35 minutes or less from LEX Bluegrass Airport, Keeneland and Shaker Village. See guidebook for more info.

Luxury Retreat with Hot Tub

Welcome to Four Seasons Cottage on the Bourbon Trail! This charming property is located in a peaceful vacation community, just a short walk from the seasonal pool. Featuring 2 bedrooms, a fully equipped kitchen, and cozy living room with a fireplace, this cottage is perfect for a family getaway or a couples retreat. Enjoy the large deck with a hot tub and BBQ, as well as access to nearby hiking trails and attractions. Cottage 37 sits on a ridge that overlooks the 3,050-acre Taylorsville Lake.

Tyler Park Cottage in the Highlands

Adorable, light-filled cottage in the beloved Highlands neighborhood. An easy ten minute walk in one direction will put you on Bardstown Road, full of dining and bars, while a 15 minute walk in the other will land you in the hip Germantown-Schnitzelburg neighborhood. A short (6 minute) drive to downtown, 11 minutes to Churchill Downs. You'll find wireless internet, clean towels and sheets, basic kitchen and bathroom amenities, coffee maker, a flat screen TV with Apple TV, and keyless entry.

ArTisTs CoTTaGe

Enjoy peaceful privacy with center city convenience! Bright, open ambiance. Art and music supplies, books, toys, games, CD's, movies. Two decks and a covered patio. Found art gardens and galleries. Fully equipped kitchen with granite counters. Large windows in downstairs bedroom with queen bed and gas fireplace. Ladder access to queen bed in skylit loft. A perfect getaway for artists/writers on retreat, solo adventurers, couples, business travelers and small families with well behaved kids.

Bourbon Barrel Cottages 2 Ky Bourbon Trail HOT TUB

Leave the Cleaning to Us – Your Bourbon Country Escape Awaits! Kick back, relax, and unwind in a stylish, serene retreat nestled in the heart of Kentucky’s Bourbon Country. Welcome to Bourbon Barrel Cottages, where nature, comfort, and convenience come together. Each of our five private two-bedroom cottages sits on its own two-acre lot, surrounded by wildlife and natural beauty—perfect for couples, friends traveling together, or anyone seeking peace and privacy. You'll Love Staying with Us!

The Cottage Circa 1898 Downtown Location

Charming 1800's cottage listed on the National Register of Historic Places in Bardstown. Voted Most Beautiful Small Town in America. Walking distance from downtown shopping, nightlife, dining, and local attractions. Located along the Kentucky Bourbon Trail. I love Bardstown and wanted my cottage to look and feel like what is best about the town- historical charm mixed with modern amenities. Clean, cozy and comfortable; it is a space that I hope you find enjoyable while visiting Bardstown.

The Gathering Place

The Gathering Place is the perfect place to get away and gather with family and friends. The resort is located conveniently between Bardstown, Louisville, and Frankfort on the Bourbon Trail. Offseason hiking, fireplace, and hot tub make a great peaceful getaway or work from "home" experience. Enjoy fishing, boating, kayaking, hiking, bird/deer watching and relaxing. The owners have been Resort guests for years and now own a cottage to enjoy and share with family, friends, and guests.

Lake Livin' & Bourbon Sippin'

Edgewater Resort, 20 minutes from Louisville, is Taylorsville Lake's premier vacation spot, tucked away in a gated community with over 163 acres that overlooks the marina. Within walking distance you'll find a community pool (seasonal) with a sand volleyball court and a fire pit. This two-story cottage sleeps up to 10 guests and showcases a master suite with two private balconies and a jetted soaking tub. You can also hang out on the private deck out back equipped with a 4-person hot tub.

Lakeside Cottage -upgraded hot tub- Bourbon Trail!

Welcome KY visitors, horse lovers, Bourbon Trail guests, or anyone looking for a getaway! This is a somewhat rustic, homey, comfortable 20 year old cottage. It's not perfect, but our guests find it charming and sufficient. You'll find the home exactly as described with the offerings and expectations. Rest, relax, and recharge in a gated community overlooking Taylorsville Lake. Don’t be another hotel's customer when you can stay in a spacious home with a Jacuzzi J-235 hot tub.

Charming South Frankfort Cottage!

Great private guest house in the heart of South Frankfort! Only a 5-10 minute walk to all the Historic Downtown Frankfort and the Kentucky Capitol. Great location for the Bouron Trail (especially Buffalo Trace and Woodford Reserve) and the KY River. We are also close to Keeneland and the Horse Park. Come enjoy what our community has to offer! We pride ourselves in hosting families and friends who want an affordable place to stay!

2 BD 1 BA Serene Setting Retreat House

Carriage home is located on beautiful Arnoldtown Rd. 15 min. from Churchill Downs and 20 min. from downtown Lou. We are 15 minutes from Freedom Hall or the Fairgrounds and 22 miles from Fort Knox. It sits in a natural setting on 5 beautifully landscaped acres. There is a large parking area for those who may need to bring a trailer. Bathroom and bedrooms are on the 2nd floor. Peaceful..in a rural setting but inside the city.

Cozy Cottage on Famous Kentucky Farm

Charming renovated cottage on Foxhollow Farm - a biodynamic grassfed beef farm near Crestwood, KY. Enjoy horse views, private nature trail access, and peaceful countryside living. Fully equipped kitchen, WiFi, Smart TV. Featured on Bravo's Top Chef Kentucky. Minutes from bourbon distilleries, upscale dining, and Louisville attractions. Perfect weekend escape!