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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Top guest favorite
A spacious outdoor area features a stone fire pit surrounded by four Adirondack chairs. A gravel path leads up to a large deck, providing ample space for relaxing and enjoying nature. The natural surroundings are dotted with greenery and stones.
Yurt in Smiths Grove
4.99 out of 5 average rating, 176 reviews

Mammoth Cave Yurt Paradise!

Just 11 miles from the world's longest cave system, Mammoth Cave National Park, our yurt provides a unique glamping experience with many modern amenities. Inside, cook in the full kitchen or snuggle up and enjoy your favorite show on our smart TV. Outside, sit on our large private deck or around a stone fire pit where you can relax and enjoy the sounds of nature. Whether you're looking for a quiet retreat or an adventure-filled getaway, our yurt is the perfect choice for your next vacation.

Guest favorite
A serene view of the Barren River is captured from a wood deck, surrounded by lush trees and misty landscapes. The gentle light of dawn reflects on the water, creating a tranquil atmosphere. The cabin's modern structure is visible on the left, enhancing the natural setting.
Cabin in Bowling Green
4.94 out of 5 average rating, 792 reviews

Riverside Cabin | Mammoth Cave | Bowling Green, KY

Our cozy Riverside Cabin is a place of peace, 15 minutes from downtown Bowling Green. Our retreat is located uniquely, between the beautiful Barren & Gasper Rivers. This is a unique, unplugged experience for a romantic get-away. We don't have WiFi, and cell service is sparse. Prepare for an experience with your favorite person, with nature flourishing all around you. We insist our guests enjoy a 5 star experience, so if there's anything you'd like provided, ask, and we'll do everything we can.

Top guest favorite
Home in Smiths Grove
4.93 out of 5 average rating, 345 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
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, 389 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 spacious living room features warm wood paneling and high ceilings, complemented by a large, plush sofa and loveseat. A coffee table centers the area, while a smart TV and decorative accents enhance the cozy ambiance. Natural light enters through multiple windows with simple coverings.
Cabin in Scottsville
5 out of 5 average rating, 125 reviews

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.

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, 211 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
Cabin in Smiths Grove
4.97 out of 5 average rating, 216 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, 116 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 single-story house is presented with a green exterior and a welcoming front porch. The porch is furnished with two chairs, while a grassy yard leads to the entrance. Large windows allow natural light to stream inside, highlighting the home’s charm.
Cottage in Bowling Green
4.95 out of 5 average rating, 212 reviews

The Sweet Pea

This newly decorated house is close to everything, less than a mile from interstate making it easy to plan your visit. Do you love racing, the Sweet Pea is located .4 miles from The National Corvette Motorsports Park, .8 miles from The National Corvette Museum, and 6.7 miles to Beech Bend Park. The Sweat Pea has a large circle drive that should accommodate any of your parking needs. 20 miles from Mammoth Cave, 14 to Lost River Cave, and 4.7 miles to WKU campus.

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
4.91 out of 5 average rating, 220 reviews

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.

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, 247 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
Apartment in Bowling Green
4.92 out of 5 average rating, 140 reviews

Live Like a Local ~ Downtown BG @ Armory Lofts

Located in the heart of downtown Bowling Green, this loft style 625 square feet apartment is everything you need. Within walking distance to many local restaurants and venues, you'll be sure to find something of interest. Near the Corvette Museum, Beech Bend Park and Raceway, Lost River Cave, and a short drive to Mammoth Cave National Park.

Popular amenities for Oakland vacation rentals

  1. Airbnb
  2. United States
  3. Kentucky
  4. Warren County
  5. Oakland