Vacation rentals in Oakland

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Oakland

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Home in Smiths Grove
4.93 out of 5 average rating, 366 reviews

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!

Guest favorite
A spacious brick home is set against a backdrop of lush greenery. The front porch is adorned with potted plants, and a stone walkway leads to a well-maintained lawn. Large windows and a welcoming entrance reflect the serene country setting.
Home in Smiths Grove
4.93 out of 5 average rating, 100 reviews

Texie’s Treasure on the Hill

Forget your worries and feel like you’re at grandmas house again ,in this spacious and serene space.A Victorian home located in a beautiful country area . Located beside Tayvin Gardens Venue..approximately 17 miles from Beach Bend Raceway , 7.5 Miles from Mammoth Cave National Park , 14 miles to the Mammoth Cave Visitor Center, 10 miles from National Corvette Museum, 25 miles from Nolin Lake State Park, 6 miles to the New Buc-ee’s Smiths Grove, Ky, 15 miles Medical Center for traveling Nurses

Guest favorite
The beautifully crafted exterior of the Tuscan-inspired home is featured, showcasing cream-colored walls and multiple large windows. Lush greenery, including manicured bushes, surrounds the house, while a well-maintained lawn extends to the front steps, providing an inviting entrance.
Home in Smiths Grove
4.94 out of 5 average rating, 399 reviews

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

Top guest favorite
The exterior of the tiny guest home is shown, featuring a welcoming porch with two gray chairs positioned beside the entrance. A simple wreath adorns the white door, while neatly arranged stone steps lead to a landscaped area with fresh greenery.
Guesthouse in Scottsville
4.96 out of 5 average rating, 229 reviews

Adorable Guesthouse close to Barren River Lake #1

Tiny guest home is beautifully decorated & extremely comfortable. We provide snacks including chocolate, 2 bottles of water, coffee pods, high quality linens & thick mattress toppers. Peaceful surroundings, kitchen is equipped w/ refrigerator, microwave, hot plate, coffee bar & 55”television. Exterior outlet for boat hookup. Spacious parking. 20 minute drive to Mammoth Cave, 4 miles to Barren River Dam & Dock. Unit is close to main house, so if you forget something, we have you covered.

Top guest favorite
The historic log cabin features a welcoming front porch with four rocking chairs, inviting relaxation amidst the surrounding greenery. The exterior showcases traditional wooden beams and a rustic charm, while a small garden area is visible, enhancing the tranquil atmosphere of the property.
Cabin in Smiths Grove
4.97 out of 5 average rating, 230 reviews

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.

Guest favorite
A cozy living area features a rich blue sofa with decorative cushions. Exposed brick walls add texture, complemented by framed artwork of guitars and a horse. Large windows allow natural light to fill the space, with a dining area visible through the archway.
Apartment in Smiths Grove
4.89 out of 5 average rating, 121 reviews

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.

Top guest favorite
A circular firepit area is surrounded by several dark wooden Adirondack chairs, providing ample seating. Two suspended hanging chairs add comfort. The landscape features lush greenery and smooth stones, while warm light strings create a cozy atmosphere for gatherings.
Home in Brownsville
4.99 out of 5 average rating, 201 reviews

The Cave Retreat - 4 Minutes from Mammoth Cave!

Escape to nature and book your stay at our serene Mammoth Cave retreat! Our spacious and modern home is located just minutes from the national park and offers stunning views of the surrounding wilderness. Enjoy the cozy fireplace, prepare a meal in our fully equipped kitchen, or roast some marshmallows under the stars. With comfortable bedrooms and ample living space, our home is perfect for families or groups of friends. Book now and experience the tranquility of Mammoth Cave!

Top guest favorite
A well-equipped kitchen features wooden cabinetry and modern appliances. A dining table made of natural wood is set in the center, surrounded by chairs. A cozy sitting area is positioned along the wall, with a staircase leading to a loft space above, under wooden beams.
Cabin in Bowling Green
4.99 out of 5 average rating, 263 reviews

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

Top guest favorite
A cozy living area features a soft leather sofa with yellow accent pillows and a textured ottoman. A plush throw is draped over the ottoman. The background reveals a sleeping area with a white bed adorned with a yellow blanket, illuminated by natural light from a nearby window.
Tiny home in Brownsville
4.93 out of 5 average rating, 402 reviews

Cute and Cozy tiny home

You won’t forget your time in this romantic, memorable place. It is newly renovated. Perfect for a short getaway or a long stay. Peaceful Country setting but close to many attractions. Enjoy hiking and sightseeing at Mammoth Cave. Short drive to Bowling green for Corvette museum…and many other options for sightseeing/shopping. Has full kitchen with all the essentials. Fireplace. Outdoor patio/porch.

Top guest favorite
A charming farmhouse exterior is shown, featuring a white façade, red shutters, and a welcoming porch with seating. The property is surrounded by green grass and trees, under a clear blue sky, creating a peaceful rural setting.
Farm stay in Smiths Grove
4.96 out of 5 average rating, 190 reviews

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

Top guest favorite
A rustic welcome sign is displayed against a brick wall. The sign features the text 'WELCOME TO NONNA'S PLACE' in bold green letters, accompanied by a bright sunflower illustration. The phrase 'WEEKENDS WEEKDAYS WHENEVER' is included in a smaller font below.
Barn in Oakland
4.99 out of 5 average rating, 146 reviews

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.

Top guest favorite
Cabin in Brownsville
4.95 out of 5 average rating, 238 reviews

Cozy Cabin near Mammoth Cave

A place in the country you’ve always wanted to visit. Only 10 minutes from Mammoth Cave National Park! We also have a fire pit for your enjoyment. Complete with firewood! In addition to Mammoth Cave, there are so many things to do in this area. Feel free to reach out for more information! And now with 100Mbs fiber internet!

Popular amenities for Oakland vacation rentals