Holiday houses in Kentucky

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Top-rated holiday rentals in Kentucky

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Guest favourite

Cottage in Wilmore

4.98 out of 5 average rating, 162 reviews

River House - Cottage with KY River View & Access

Come relax at the peaceful river house. It feels like a retreat right on the Kentucky River with a party-sized dock for easy river access. It’s a cozy cottage on stilts with a breakfast bar on the porch and swing on the patio. Be surrounded by nature and beautiful views of the river and palisades. Tuck away in seclusion just minutes away from downtown Wilmore, Asbury University & Seminary. 35 minutes or less from LEX Bluegrass Airport, Keeneland and Shaker Village. See guidebook for more info.

29 Aug – 5 Sep

$235 NZD per night

Guest favourite

Home in Stamping Ground

4.97 out of 5 average rating, 604 reviews

Buffalo Springs Distilling Company

On the Bourbon Trail The Buffalo Springs Distilling Company got it's start in 1868. It closed and it's warehouses were emptied out by the 1970's. This building is one of the last structures left on the site. This historic building was the main office and gatehouse for visitors to the distillery, so we can offer one bedroom due to the size of the structure. Queen size bed in the bedroom. There’s also a Queen Air Mattress that can be utilized in a pinch for folks that are staying at least a week

22–29 Mar

$292 NZD per night

Guest favourite

Train in Lawrenceburg

4.98 out of 5 average rating, 260 reviews

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

2–9 Sep

$310 NZD per night

Guest favourite

Cabin in Bowling Green

4.94 out of 5 average rating, 708 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 nestled in a canopy of trees along the beautiful Barren River. This is a wonderful location for a romantic get-away, or for serenity seekers. We don't have WiFi, and cell service is sparse, so prepare for an unplugged experience, 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!

12–19 Nov

$350 NZD per night

Guest favourite

Barn in Campbellsville

4.95 out of 5 average rating, 99 reviews

Peaceful Getaway in the Country

Enjoy this rustic, yet cozy, two-story barnhouse located near bourbon country. Perfect for a couple's getaway, it has open lofts with a comfy king-sized bed, a kitchen stocked with all the essentials, laundry room, wood burning stove & two bathrooms: one with a walk-in shower & one with a soaker tub. This listing's interior is ready, however the exterior is still a work in progress as we continue to create comfortable outdoor spaces. Must see all pictures to appreciate what this place offers.

1–8 Oct

$159 NZD per night

Guest favourite

Cabin in Pine Ridge

4.98 out of 5 average rating, 124 reviews

Cliffside Romantic Retreat LOVE

Fall in love at the unique and tranquil getaway of the "Tis So Sweet Cliffside Cabin". The space is designed for a lovers retreat with luxuries of a spa bathroom, massage chair, fire table, recliner seat hot tub, and much more! This newly built cabin is peacefully secluded, yet still only a few miles away from the Natural Bridge State Park, Red River Gorge, Daniel Boone National Forest, underground kayaking, zip lines, rock climbing, swimming, delicious food and many other local attractions.

12–19 Dec

$469 NZD per night

Guest favourite

Cabin in McKee

4.99 out of 5 average rating, 135 reviews

The Cabin on Panther Branch

Drive down Kentucky scenic highway 89 South just 9 miles south of McKee. The cabin is newly built and set back in a secluded area with a small creek running right beside the cabin and a larger creek just across the road. The Cabin on Panther Branch is a perfect place to come fish and kayak on the creek. Bring your ATV’s, side by side or dirt bikes and enjoy miles and miles of riding in S-Tree Tower in the Daniel Boone National Forest. We don’t think you will be disappointed with your stay.

1–8 Apr

$200 NZD per night

Guest favourite

Tiny home in Corbin

4.98 out of 5 average rating, 239 reviews

Pet Friendly True Tiny Home

This is a great stay for outdoor enthusiasts, pet lovers, or those travelling and want a homey and private place to stay for the night. The house is located in the country, but approximately 5 minutes from 1-75, 5 from Laurel Lake, 15 from Corbin, and 30 from London. Huge outdoor space which includes 1 acre private lot, large screened in porch with dinning area, a fire pit with chairs and picnic table, and fenced in back yard. Sleeps 3: upstairs loft bed is a full, downstairs is a twin.

11–18 May

$145 NZD per night

Guest favourite

Treehouse in Georgetown

4.94 out of 5 average rating, 168 reviews

★Escape & Relax ~ Breathtaking Creekside Getaway★

Escape the everyday hustle and bustle by immersing in the stunning glamping experience on a secluded creekside property. Enjoy solitude, romance or family time inspired by nature. Tucked away on our 13 acre residence, this spacious 16' tent offers a unique stay in a breathtaking ambiance. ✔ Queen Bed + 2 Full-Size Mattresses ✔ Outdoor Deck with Seating ✔ Bathtub + Separate Shower ✔ Composting Toilet ✔ Creek Access + Kayaks ✔ Cooking Station Learn more about this glamping haven below!

12–19 May

$332 NZD per night

Guest favourite

Cabin in Berea

4.92 out of 5 average rating, 168 reviews

A Happy Place Cabin with magical views!

A cabin and experience like no other in Berea. Enjoy the smell of cedar, sounds of the country, amazing views of the mountains and magical sunsets! Relax in our cozy all cedar cabin that sits on a 37 acre property. Fish in the large pond, swing on the porch, and cook dinner outside on the Blackstone griddle. Located just 5 miles from town, it is close enough to find great dining options and visit all that Berea has to offer, yet far enough away to provide serene tranquility and peace.

3–10 Aug

$245 NZD per night

Guest favourite

Tiny home in Franklin

4.98 out of 5 average rating, 398 reviews

Couple’s Getaway! *Tiny House Country Retreat

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).

27 Jul – 3 Aug

$174 NZD per night

Guest favourite

Cabin in McKee

4.99 out of 5 average rating, 217 reviews

Peaceful getaway for couples - Hemlock Haven LLC

*Please read entire listing and rules* Step away from fast paced life to experience true relaxation at our tiny cabin, situated in the one stop light town with some of the country's best internet! Located in the heart of the Daniel Boone National Forest, Hemlock Haven LLC has been customized to be a nature lovers paradise. Our cabin is in a fairly remote area, but we do have a few local convenience stores and restaurants where you'll find plenty of hospitality and country cooking!

7–14 Aug

$283 NZD per night