Holiday rentals in Oakland

Country setting near Mammoth cave , Barren River

Keep it simple and peaceful at the Dossey place! Our farm is centrally-located, just minutes from I-65. The house sits at the end of a 400 foot long driveway on a 90 acre farm. The corvette museum, beech bend park, WKU, shopping, restaurants, mammoth cave national Park, Nolan lake, cave city, and Kentucky down under are only a short drive away from the farm! Unique features include: a fire-pit, a barn that can house horses, and a front porch that provides a perfect view of the sunset daily!

Vineyard House At Bluegrass Vineyard & Winery

Tuscan-inspired Airbnb connected to the Bluegrass Vineyard tasting room and winery. The home is easily accessible to I-65, yet is quietly nestled in the countryside among rolling hills. This listing includes 3 bedrooms with a King and two Queen beds, 2 bathrooms, kitchen, living room, dining room, and outside patio areas. We have a large 80 gallon hot water heater, so you don't run out! This home is connected to the winery via a door that remains locked unless cleaning. License No: WC0038

Bungalow In The River Bend

Private, Quiet, Clean. Located off I-65 Exit 28 w/in 1/2 mile of Corvette Factory & National Corvette Museum & NCM Motorsports Park. Note: Traveling professionals we are 7 min (2.7 mi) to Medical Center & 14 min (5.4 mi) to TriStar Greenview Regional Medical Center. Mammoth Cave, Beech Bend Raceway, WKU, Lost River Cave, Bowling Green Hot Rods, Southern KY Performing Arts, Historic Riverview at Hobson Grove, KY Museum. We are 109 miles south of Louisville & 67 miles north of Nashville.

Liberty Hills Cabin | Hot Tub | Fire Pit

Welcome to our cozy cabin on our picturesque 146-acre farm! Escape to a beautifully remodeled cabin that is nestled within the rolling hills of a cattle farm. It boasts panoramic views from its front and back porches. Whether you just want to relax and enjoy the quaint, peaceful, country setting or explore nearby attractions, this 2023 renovated cabin is your perfect retreat. Conveniently located just 10 min from Scottsville, 15 min from Bowling Green, and 15 min from Barren River Lake.

Adorable Guesthouse #2 Close to Barren River Lake

We are excited to present our tiny guest home #2. Perfect for the fisherman or couple wanting to stay close to Barren River Lake or Mammoth Cave. This unit is centrally located between several towns and less that four miles from Port Oliver Boat Ramp and Dam. It is close to the main house so we will be available if you need anything. Peaceful surroundings, comfortable queen bed, refrigerator, microwave and coffee bar. 55" smart tv to kick back & relax with. Exterior outlet for boat.

1830s Log Cabin • 5 Acres Near Mammoth Cave

Experience a one-of-a-kind 1830s historic log cabin just 7 miles from Mammoth Cave National Park. On 5 secluded acres, this pre-Civil War home blends original hand-hewn wood beams & antique charm with modern comforts like WiFi, a smart TV, & a full kitchen. Perfect for romantic getaways, family vacations, & nature escapes, it offers access to local attractions, hiking trails, & Kentucky’s cave country. Enjoy peaceful mornings on the porch, nights by the fire pit, & year-round beauty.

The Loft off Main I

Enjoy the center of the antique district of Smiths Grove centrally located to Mammoth Cave NP and Bowling Green. Stroll around Main Street visiting the unique local shops, treat yourself to an ice cream cone from the Flavor Isle or jump right on I65 and head to Bowling Green or Mammoth Cave for a day of adventure! This great loft apartment is in a building over 100 years old and the character is cozy and gorgeous. Please note this apartment is on the second floor of the building.

Gorgeous Log Cabin close to Cave and Lakes!!

Private 3 bed 2 bath Log Cabin retreat close to Barren River Lake/Mammoth Cave with amazing shops if you love antiques! Enjoy the country side while close to any amenities you may need. Large Front and Back porch along with an outdoor kitchen and hot tub to accommodate you and your guests. Come relax, grill, enjoy the country whether you are here looking for a place to reside or wanting to get away from the city! Coffee, wifi and games provided.

Tiny Cabin in the woods!

Tiny cabin in the woods about 30 minutes from Mammoth Cave, and 20 minutes from WKU, Historic Downtown Bowling Green, Beech Bend Raceway and the National Corvette Museum! You will enjoy a peaceful setting hidden in the trees, a fully-stocked kitchen, Fiber Wi-Fi, hot tub and fire pit. Enjoy picking blackberries late June and July! Need more space? Check out our other listing with additional sleep space: https://www.airbnb.com/slink/Cor5Q5Gm

Cozy Farmhouse Cottage

Cozy, open studio (one room/all open) 400 square foot house quietly tucked away on our farm. Enjoy the farm view from the front porch or the screened in back porch. -Minutes from I-65. -A short drive to Mammoth Cave, Barren River, Corvette museum, Beech Bend or downtown Smiths Grove antique district. -Plenty for parking for boats or trailers. Friendly reminder: this is a working farm with cattle and horses. WC0006

Cute Farmhouse close to Mammoth Cave/Bowling Green

Adorable farmhouse centrally located between Mammoth Cave, National Corvette & Barrren River Lake! This house is stocked with everything you will need for a getaway or just a break from city life. Relax in the country or enjoy all the nearby attractions! The kitchen is stocked with essentials, the beds are comfy and the views are beautiful and relaxing! We can’t wait for you to visit! WC0033

Nonna’s Place Pole Barn Dwelling Near Mammoth Cave

This is a renovated Dairy Barn transformed into a two bedroom home away from home located in Oakland, KY on a 150+ acre farm. It is 2 mins from I-65 south, 5 mins from 1-65 north, 10 mins from the Corvette Museum, and 20 mins from Mammoth Cave National Park, Nolin Lake, Beech Bend Raceway, and Western Kentucky University. It is located between Nashville, TN and Louisville, KY.