Holiday rentals in Oakland

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Top-rated holiday rentals in Oakland

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

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Top guest favourite
A newly constructed cottage is nestled among trees, featuring a blue exterior and a sloped metal roof. A covered porch with a rocking chair invites relaxation. A gravel path leads to the entrance, surrounded by lush greenery.
Cottage in Mammoth Cave
4.97 out of 5 average rating, 199 reviews

Serene Cottage for Outdoor Enthusiasts #2

Keep it simple at this peaceful and centrally-located place. Newly constructed Cottage in wooded area adjacent to Nolin River Lake. Less than a mile to boat ramp. Within 5 minutes of MCNP boundary. 30 minute drive to the MCNP Visitor Center. 5 minute drive to Nolin Lake State Park. 5 minutes from Blue Holler Off-road Park, Hiking And Horse back riding trails. Within 1 mile of the Nolin River, which is designated as Kentucky s first National Water Trail. 15 minutes from Shady Hollow Golf Course.

Top guest favourite
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, 141 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.

Top guest favourite
A newly constructed private home is visible, featuring a gray exterior with a pitched roof. The front porch is partially shaded, and a gravel driveway leads up to the house. Surrounding grassy areas and trees are seen in the backyard.
Home in Cave City
4.91 out of 5 average rating, 186 reviews

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.

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, 371 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 dark cabinetry, white subway tile backsplash, and stainless steel appliances. A spacious wooden island provides seating for four with woven stools. Natural light floods in through large windows, highlighting the warm reclaimed wood flooring and vaulted ceiling with rustic beams.
Farm stay in Scottsville
4.98 out of 5 average rating, 261 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.

Top guest favourite
The exterior of a rustic cabin features a combination of log siding and a green metal roof. A spacious covered porch welcomes guests, with large columns supporting the overhang. Surrounding trees provide shade and natural beauty, enhancing the serene rural setting.
Cabin in Russellville
4.96 out of 5 average rating, 154 reviews

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.

Top guest favourite
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.
Guest house in Scottsville
4.96 out of 5 average rating, 187 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
Tiny home in Franklin
4.98 out of 5 average rating, 561 reviews

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).

Top guest favourite
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, 191 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
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, 512 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

Guest favourite
A cozy seating area features a dark gray sofa adorned with two decorative pillows displaying farm-themed images. A small side table with a lamp provides soft lighting. A 'gather' sign hangs above, and a window with blinds offers natural light, complemented by a framed picture on the wall.
Cottage in Smiths Grove
4.94 out of 5 average rating, 469 reviews

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

Top guest favourite
A cozy living area features a soft leather sofa with yellow accent pillows and a textured ottoman. A plush throw is draped over the ottoman. The background reveals a sleeping area with a white bed adorned with a yellow blanket, illuminated by natural light from a nearby window.
Tiny home in Brownsville
4.93 out of 5 average rating, 310 reviews

Cute and Cozy tiny home

You won’t forget your time in this romantic, memorable place. It is newly renovated. Perfect for a short getaway or a long stay. Peaceful Country setting but close to many attractions. Enjoy hiking and sightseeing at Mammoth Cave. Short drive to Bowling green for Corvette museum…and many other options for sightseeing/shopping. Has full kitchen with all the essentials. Fireplace. Outdoor patio/porch.

Popular amenities for Oakland holiday rentals

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