Holiday houses in Oakland

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Top-rated holiday rentals in Oakland

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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, 151 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 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, 773 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 favourite
Treehouse in Franklin
4.99 out of 5 average rating, 164 reviews

Treetop Views *Trails, Fishing *No Cleaning Fee

Amazing two-story house nestled high up in the trees. A true treehouse! This treehouse sits amongst a forest of poplar trees and feels very secluded and private. It has spectacular views of Kentucky’s rolling hills as it looks out across the valley. This treehouse was hand built and handcrafted with love and attention to detail. 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).

Guest favourite
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, 326 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
A tiny house is depicted, featuring a dark exterior with red accents around the windows and door. A wooden deck surrounds the entryway, complemented by a railing. Open countryside is visible in the background, with expansive fields and a clear blue sky.
Tiny home in Rockfield
4.97 out of 5 average rating, 100 reviews

Private, Tranquil Tiny Home With Countryside Veiws

Just 20 minutes from downtown Bowling Green and one hour from Mammoth Cave, Nolan Lake, Barren River Lake and other outdoor attractions. Our Tiny Home is a private, cozy, tranquil retreat nestled on 5 acres in the Rockfield, KY countryside. We hope you enjoy all the thoughtful elements we put into our tiny home! So read a book, play a board game, sit on the porch, or back deck and soak in the views while allowing yourself to relax, and unwind from the stresses of the world. License # WC00

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

Guest favourite
A bungalow with a covered porch is depicted, featuring a welcoming red door and white siding. Four light green chairs are arranged on a grassy area in front of the house, surrounded by trees. The carport is visible to the right, providing additional outdoor space.
Bungalow in Bowling Green
4.92 out of 5 average rating, 390 reviews

Bungalow In The River Bend

Private, Quiet, Clean. Located off I-65 Exit 28 w/in 1/2 mile of Corvette Factory & National Corvette Museum & NCM Motorsports Park. Note: Traveling professionals we are 7 min (2.7 mi) to Medical Center & 14 min (5.4 mi) to TriStar Greenview Regional Medical Center. Mammoth Cave, Beech Bend Raceway, WKU, Lost River Cave, Bowling Green Hot Rods, Southern KY Performing Arts, Historic Riverview at Hobson Grove, KY Museum. We are 109 miles south of Louisville & 67 miles north of Nashville.

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.
Guesthouse in Scottsville
4.96 out of 5 average rating, 193 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, 199 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 favourite
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
4.92 out of 5 average rating, 208 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 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, 218 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, 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

Popular amenities for Oakland holiday rentals

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