
Holiday rentals in Oakland
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Oakland
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

2 BR Beautiful new home near Mammoth Cave.
Relax with the whole family at this very pleasant place to stay. This is a fully furnished 2 bedroom & 1 bath private home. It's also a new build in 2024 and designed for family vacations. You'll have 2 Queen size beds in this country home. This house will sleep 4 easily. It is just 5-10 minutes away from Mammoth Cave and all of the featured attractions. Plenty of closet space, your own kitchen and a television in every room. We will allow 5 people and the couch and recliners will also recline.

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!

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

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.

Cozy Cabin with Private Walking Trail
Relax and retreat to this peaceful rural cabin with modern amenities and charming outdoor spaces situated on a working farm. Enjoy the walking trail through 10 acres of woods or swing while enjoying beautiful country views. Experience the best of both worlds in the historic 19th century cabin with a modern addition. A short drive to quaint downtown Russellville, Auburn, or Franklin KY each with plenty of shopping. The nearby Red River provides opportunities for kayaking, tubing or fishing.

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.

Tiny Living! Trails, Fishing *No Cleaning Fees
Our beautiful rustic tiny house cabin is the perfect couples getaway or just a great place to stop in for the night. Our tiny house sits down by our pond tucked away into the woods and is very private and secluded. Sit out on the front porch and watch the deer. Play games, read a book, go fishing or just rest and relax. Located just off of I65 outside the historical little town of Franklin, KY. We are located between Nashville (45min), Bowling Green (35min) and Mammoth Cave (55 min).

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.

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.

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

Cozy Farmhouse Cottage
Cozy, open studio (one room/all open) 400 square foot house quietly tucked away on our farm. Enjoy the farm view from the front porch or the screened in back porch. -Minutes from I-65. -A short drive to Mammoth Cave, Barren River, Corvette museum, Beech Bend or downtown Smiths Grove antique district. -Plenty for parking for boats or trailers. Friendly reminder: this is a working farm with cattle and horses. WC0006
Popular amenities for Oakland holiday rentals
Other great holiday rentals in Oakland

Meadow Lane Cabin

Spring Break National Park Trip | Hot Tub + Games

Tiny Loft #1

Cute Farmhouse close to Mammoth Cave/Bowling Green

Cozy Cottage in Scottsville KY

Texie’s Treasure on the Hill

The Cottage at Black Lick Creek

Spend Your Nights on Broadway -License No. SG0001
Destinations to explore
- Western North Carolina Holiday rentals
- Nashville Holiday rentals
- Atlanta Holiday rentals
- Gatlinburg Holiday rentals
- Pigeon Forge Holiday rentals
- Asheville Holiday rentals
- Indianapolis Holiday rentals
- Southern Indiana Holiday rentals
- St. Louis Holiday rentals
- Columbus Holiday rentals
- Louisville Holiday rentals
- Cincinnati Holiday rentals




