Holiday houses 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 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, 173 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 modern cabin is surrounded by lush greenery, featuring a dark exterior and a sloped metal roof. A wooden deck leads to the entrance, while stone walls create a landscaped area. Natural light filters through large windows, enhancing the inviting appearance of the cabin.
Cabin in Bowling Green
4.94 out of 5 average rating, 790 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
Home in Smiths Grove
4.93 out of 5 average rating, 342 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!

Guest favourite
Home in Smiths Grove
4.94 out of 5 average rating, 388 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
An inviting outdoor space is featured, illuminated by soft lights. A hot tub sits next to a fire pit, surrounded by chairs, providing a cozy atmosphere for evening relaxation. A tree adds height to the background, enhancing the connection with nature.
Cabin in Scottsville
5 out of 5 average rating, 122 reviews

Liberty Hills Cabin | Hot Tub | Fire Pit

Welcome to our cozy cabin on our picturesque 146-acre farm! Escape to a beautifully remodeled cabin that is nestled within the rolling hills of a cattle farm. It boasts panoramic views from its front and back porches. Whether you just want to relax and enjoy the quaint, peaceful, country setting or explore nearby attractions, this 2023 renovated cabin is your perfect retreat. Conveniently located just 10 min from Scottsville, 15 min from Bowling Green, and 15 min from Barren River Lake.

Top Guest favourite
Guesthouse in Scottsville
4.96 out of 5 average rating, 208 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, 213 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
Apartment in Smiths Grove
4.88 out of 5 average rating, 113 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.

Top Guest favourite
The townhouse features a well-maintained brick facade with multiple large windows. A prominent tree is centrally located in the front yard, surrounded by neatly trimmed grass and landscaping. Sidewalks provide clear pathways to the entrance, enhancing accessibility to the unit.
Townhouse in Bowling Green
4.99 out of 5 average rating, 141 reviews

Roomy 3BR/2.5ba WKU, Mammoth Cave, Corvette Museum

Townhouse getaway features lots of amenities for up to six guests. Perfect for couples or family travelers and located in a residential area close to Western Kentucky campus, all major retail stores and a variety of dining establishments. One hour north of Nashville and two hours south of Louisville, and 33 miles from Mammoth Cave. Close to multiple recreational lake facilities, the National Corvette Museum and a vast array of recreational activities.

Guest favourite
An outdoor hot tub is illuminated with red lights, creating a relaxing ambiance. In the background, a wooden porch is visible, featuring a front door and a glimpse of the cabin structure. The space is designed for evening enjoyment and leisure.
Cabin in Smiths Grove
4.91 out of 5 average rating, 220 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
Cabin in Bowling Green
4.99 out of 5 average rating, 243 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

Guest favourite
Cottage in Smiths Grove
4.94 out of 5 average rating, 479 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

Popular amenities for Oakland holiday rentals

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