Vacation rentals in Oakland

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Top-rated vacation rentals in Oakland

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

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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

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

4.93 out of 5 average rating, 106 reviews

Top guest favorite

Home in Smiths Grove

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!

4.93 out of 5 average rating, 378 reviews

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

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

4.94 out of 5 average rating, 401 reviews

Guest favorite

A bungalow with a covered porch is depicted, featuring a welcoming red door and white siding. Four light green chairs are arranged on a grassy area in front of the house, surrounded by trees. The carport is visible to the right, providing additional outdoor space.

Bungalow in Bowling Green

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.

4.92 out of 5 average rating, 414 reviews

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

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.

4.97 out of 5 average rating, 238 reviews

Top 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

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.

4.9 out of 5 average rating, 129 reviews

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

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!

4.99 out of 5 average rating, 207 reviews

Guest favorite

A log cabin with a red metal roof is situated on a grassy area, framed by trees. The spacious front porch features wooden railings and steps leading to the entrance. Natural light from the windows enhances the warm wood tones of the exterior.

Cabin in Smiths Grove

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.

4.92 out of 5 average rating, 233 reviews

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

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

4.99 out of 5 average rating, 272 reviews

Guest favorite

A dining area is showcased, featuring a round wooden table surrounded by two chairs. Natural light streams through a window above the table, with a vintage cupboard and decorative items lining the walls. The ceiling displays corrugated metal, adding character to the space.

Place to stay in Alvaton

studio apt w/bridge o/gorge, deck, view of woods

750 sq ft studio apt with covered breakfast deck with steps to a swinging bridge and woods. Mown paths meander thru this 230-acre farm for exploring by foot or driving the 4-seater golf cart provided. Private yet accessible. Loft has king bed. Main floor living area queen sofa bed. Barn loft/party room at entry is complete with piano and double futon for the hardy campers. Covid19 cleaning standards; CCPC license #WC0026

4.98 out of 5 average rating, 537 reviews

Top guest favorite

The exterior of the single-story home is shown, featuring a light yellow siding and a covered porch. A gravel pathway leads to the entrance, surrounded by landscaped areas with small plants. The roof is dark, contrasting with the siding, and greenery is visible in the background.

Home in Brownsville

Havenly Homestead at Mammoth Cave

This Havenly Homestead is very quiet and private. We think you will find our house very relaxing and comfortable. It is surrounded by a small working farm. Only 10 minutes from Mammoth Cave National Park. There is also a fire pit for your enjoyment. Complete with some firewood! And even though the govt is shutdown, there are so many other wonderful things to do in the area. Feel free to reach out for more information!

5.0 out of 5 average rating, 157 reviews

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

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

4.96 out of 5 average rating, 193 reviews