Orlofseignir í Shelbyville

Chalet 638 - state park, golf & The Caverns

Short walk to a state park with golfing. This first floor living space has a kitchen, walk-in closet, large wood fireplace, workout equipment, washer/dryer, grill, fire pit and lots of space. Old Stone Fort Archeological Park with multiple hiking trails, fishing, canoeing and a $9 a round golf course are seconds away. Close to I-24 this centrally located Tennessee property gives equal access from Nashville to Chattanooga. Explore parks, vineyards, distilleries and Tennessee history from here.

The Whiskey at Glass Hollow | Whiskey Retreat

Stay inside the Glass Hollow experience — The Whiskey is a bold and inviting one-bedroom suite above our downtown steakhouse in the heart of Tennessee’s Whiskey Triangle. Designed with warm, rich tones and local character, it’s the perfect home base for distillery tours, dining just downstairs, and relaxed evenings. With a king bed and additional sleeping space, including a trundle, it’s ideal for couples, friends, or families looking to gather, explore, and enjoy Tennessee whiskey country.

Sycamore House

Sycamore House has three large bedrooms and three baths with plenty of room to spread out. Located in a quiet neighborhood just off Hwy. 41A (Madison Street). Great for horse shows at the Celebration or Cooper Steel Arena, tours to Uncle Nearest and Jack Daniel distillery, Bonnaroo in Manchester, Tours of Music City, and many other local sites. If you are coming for a family event in Shelbyville, my Airbnb is not for hosting parties/events/weddings etc. Near Tims Ford and Normandy Lakes.

Alpaca Ridge Ranch and Retreat

Experience the serene luxury of Alpaca Ridge Ranch and Retreat, a private, gated hilltop estate spanning 21 scenic acres in Tennessee's rolling hills. While you'll feel miles away from it all, you're conveniently located just minutes from the charm of Tullahoma, Lynchburg, and downtown Shelbyville. For whiskey enthusiasts, the estate is a quick 15-minute drive from world-renowned distilleries, including Jack Daniels, George Dickel, and Uncle Nearest. Make this your home away from home!

Riverside - Enjoy the Quiet Life on the Duck River

Welcome to life on the Duck. This quiet retreat nestled against the Duck River is a haven for gathering with family, writing your book, enjoying a cup of coffee from the screened patio, watching the river flow by, grilling, fishing, lounging by the firepit, or taking one of our 4 kayaks out. This 3 bed/3 bath house has plenty of extra space, and the Duck River boasts being the most biologically diverse river in North America and perfect for enjoying from a lazy paddle down the river!

3 Bedroom, 2 Bath Home Near Cooper Steel Arena

Enjoy this three bedroom, two bath residential home within walking distance of the Cooper Steel Arena, Tennessee Walking Horse National Celebration show grounds and near downtown Shelbyville. Amenities include a spacious fenced backyard, deck and outdoor dining area, as well as a full-size kitchen, dining and living area. Local tourist attractions include Uncle Nearest Distillery in Shelbyville and Jack Daniels Distillery in Lynchburg with only an hour commute to downtown Nashville.

Quilters Haven Cabin

Nestled on 8 acres just ¾ mile from Main Street Bell Buckle, we offer a blend of country living and small-town charm. Start your morning with a warm cup of coffee on the front porch, and relax on the back deck after exploring the area's antique shops. You may be greeted each morning by our faithful large guardian pup Dolly, and our friendly roosters and chickens. 6-miles to Nearest Green, 12-miles to George Dickel, and 21-miles to Jack Daniel's Distilleries; 50-miles to Nashville.

Bunkhouse@Rolling ThunderRanch/Monthly Rates Avail

Monthly rental available through Airbnb. No outside leasing. Studio apartment w/ queen bed, twin futon, full bath and a kitchenette area. One hour + away from downtown Nashville. The Bunkhouse is available for monthly (short-term - 3 month max*) Pets ok per review. $50 per pet fee. Max 30 lbs dog. Space is small and suitable for two adults (ideal for solo traveler). We live in a rural area so you may occasionally hear farm noises. Most find it incredibly peaceful!

The Livery at Rainbows End

If you are passionate about Walking Horses, Tennessee Whiskey or Tennessee History this is the vacation spot for you. In the heart of the Whiskey Trail and walking distance from the main gate of the internationally famous home of the Tennessee Walking Horse National Celebration. The Livery makes a perfect basecamp for your Middle Tennessee vacation. Just minutes from Jack Daniels, George Dickle and Uncle Nearest. Less than 60 miles from Nashville and Huntsville.

Hilltop Cottage • Perfect for Couples & Pets

✨ New listing—enjoy a special introductory rate! Stay at a peaceful hilltop cottage just 50 minutes from Nashville and 25 minutes from Murfreesboro. This cozy retreat sits in a quiet rural setting with a serene koi pond and Japanese-style trees. Enjoy coffee on the porch, relax by the fire pit, or unwind indoors with WiFi. Located on shared property with nearby hosts, guests still have a private entrance, space, and parking for a comfortable, relaxing stay.

Thompson

Welcome to your cozy Shelbyville getaway! Just 1/4 mile from the Horse Show Grounds and Cooper Steel Arena, this quiet retreat is close to downtown, shops, and restaurants. Enjoy high-speed Wi-Fi, a smart TV, AC/heat, and free parking. The apartment offers two comfy bedrooms — one with a queen bed and one with a full twin — ideal for couples, families, or business travelers. Thoughtfully designed for comfort, relaxation, and a pleasant stay.

Bridle & Barrel | Shelbyville Retreat

Welcome to Bridle & Barrel, your modern farmhouse in Tennessee's Walking Horse Capital! This brand-new 3-bed, 2-bath home features a stylish equestrian theme, gourmet kitchen, spacious bedrooms, and a relaxing back deck. Perfect for horse show visitors, families, or anyone seeking a country getaway. You're minutes from showgrounds and local distilleries. Enjoy the perfect blend of modern luxury and southern charm at Bridle & Barrel!