Holiday rentals in Oakland

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Top-rated holiday rentals in Oakland

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Top guest favourite
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, 150 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 favourite
A covered front porch features two rocking chairs and a small table, surrounded by potted plants. The landscape includes a well-maintained yard with flowering shrubs and a view of rolling fields under a colorful sky at sunset.
Home in Smiths Grove
4.93 out of 5 average rating, 324 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 favourite
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 favourite
A modern kitchen features a spacious wooden island with seating for several guests. Stainless steel appliances and white tiled backsplash complement the rustic reclaimed wood beams overhead. Natural light floods the area through large windows, enhancing the inviting design.
Farm stay in Scottsville
4.98 out of 5 average rating, 265 reviews

Flower Farm Modern Loft Retreat - Mammoth Cave

Peaceful privacy on our 227 acre farm, convenient to Bowling Green, Mammoth Cave, and Barren River Lake. The 900 sq ft loft above our home’s garage has private exterior entrance to the finished modern farmhouse loft with completely separate ductwork and HVAC system. The loft features everything you need to stay at the farm and relax: high end, furnished kitchen to cook meals in & fiber optic internet to work or stream. Adirondack chairs and a propane fire pit make for wonderful stargazing.

Guest favourite
Guest house in Scottsville
4.96 out of 5 average rating, 191 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 favourite
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, 198 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 favourite
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.
Flat in Smiths Grove
4.88 out of 5 average rating, 104 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 favourite
Flat in Bowling Green
4.91 out of 5 average rating, 123 reviews

Satisfying 10th Street Studio Apartment

You will be close to everything when you stay at this centrally-located studio apartment. **This private apartment is attached to the back of a main house (another Airbnb).** Minutes from WKU and downtown BG this cute little apartment can accommodate visitors coming for a short weekend stay or a more long term visit! Furry friends are also welcome for a fee. (Note - Check your pets in on the same page that you tell us how many guests are staying). We can’t wait for your visit!

Top guest favourite
An open-concept dining area showcases a simple wooden table with four black chairs. A large area rug with stripes is laid beneath the table. The kitchen features dark cabinetry and stainless steel appliances, while a wall-mounted TV is positioned nearby for entertainment.
Flat in Bowling Green
4.92 out of 5 average rating, 325 reviews

Modern Industrial Loft @ Historic Armory Lofts

600 sq. ft. urban loft located in the heart of downtown BG, walkable to WKU and all downtown attractions. This recently renovated / newly furnished 1 bed, 1 bath apartment is packed with extras including free wifi, access controlled security, washer/dryer, Keurig and complimentary kcups, dedicated parking, sound deadening construction materials, next door to Mellow Mushroom, two blocks from historic Fountain Square Park and Spencers Coffee and many great restaurants.

Top guest favourite
A cozy outdoor space is illuminated by string lights, highlighting a circular fire pit surrounded by several chairs. A stone pathway leads to the area, with trees visible in the background underscored by the cabin's silhouette at night.
Cabin in Bowling Green
4.99 out of 5 average rating, 212 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 favourite
Place to stay in Alvaton
4.98 out of 5 average rating, 517 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 favourite
Home in Brownsville
5 out of 5 average rating, 104 reviews

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!

Popular amenities for Oakland holiday rentals

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