Vacation rentals in Oakland

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Top-rated vacation rentals in Oakland

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Top guest favorite
The yurt is nestled among trees, featuring a large private deck that extends outward. Natural grassy areas surround the structure, and the exterior displays a neutral color contrasting with the greenery.
Yurt in Smiths Grove
4.99 out of 5 average rating, 158 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
The farmhouse is framed by a large tree and features a welcoming front porch with outdoor seating. A well-maintained lawn surrounds the home, with flower beds adding color. The exterior is light-colored with contrasting dark shutters, providing a charming rural appearance.
Home in Smiths Grove
4.93 out of 5 average rating, 331 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!

Top 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, 381 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 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, 204 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.

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
4.88 out of 5 average rating, 108 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.

Guest favorite
A cozy living area is presented with a brown sofa adorned with decorative cushions. A lamp stands beside the large window, allowing natural light to fill the space. A staircase leads to the upper level, while a welcoming door opens to the outside.
Cottage in Bowling Green
4.96 out of 5 average rating, 106 reviews

"Off the grid" 3 bedroom cottage in Bowling Green

Relax with the whole family at this peaceful place or have a romantic getaway. This cottage is very private located on 46 acres with 4 miles of hiking/biking trails and a fishing pond. You may see wildlife on property. It is in close proximity of the Corvette Museum, Lost River Cave, Barren River Lake, Mammoth Cave, and Nashville. You may just decide to stay in and enjoy the view and county side. Great for families and also traveling health care professionals.

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, 205 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.

Superhost
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, 212 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, 226 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 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
4.98 out of 5 average rating, 520 reviews

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

Top guest favorite
Cabin in Brownsville
4.95 out of 5 average rating, 205 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!

Guest favorite
A single-story home is showcased in a well-maintained yard, featuring a manicured lawn with striped grass patterns. The home is complemented by surrounding trees and flowers. A two-car garage is visible on the right side, along with a gravel driveway leading to the entrance.
Home in Smiths Grove
4.84 out of 5 average rating, 137 reviews

Smith's Station

Welcome to our charming vintage designed 2-bedroom home, located in the prime spot between Louisville and Nashville, just north of Bowling Green. This cozy abode is the perfect place for a relaxing getaway or a romantic retreat, and it's conveniently located near some of the area's top attractions. STR License No. SG-0007.

Popular amenities for Oakland vacation rentals

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