Holiday rentals near Chuckleberry Farm & Winery
We found 192 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals near Chuckleberry Farm & Winery that provide the perfect home base for your trip. Whether you're travelling with your children or with friends, holiday homes have the amenities that you expect for your stay, which might include Wi-Fi and a washer and dryer. No matter what you're looking for, you're sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Chuckleberry Farm & Winery
Showing deals for:1 Aug - 8 Aug
Image gallery for Bourbon Country Cabin with HOT TUB and Fire Pit on Brashears Creek
9.89.8 out of 10 rating
Exceptional
(30 reviews)
Bourbon Country Cabin with HOT TUB and Fire Pit on Brashears Creek
Shelbyville, KY
8% off
Price is NZ$3,738
NZ$3,738
NZ$534 per night
includes taxes & fees
Image gallery for Call Me Old Fashioned! *Heart of Bardstown Square*
1010 out of 10 rating
Exceptional
(39 reviews)
Call Me Old Fashioned! *Heart of Bardstown Square*
Bardstown, KY
12% off
Price is NZ$5,150
NZ$5,150
NZ$736 per night
includes taxes & fees
Image gallery for Relaxing 2800sf Countryside Bourbon Trail Home w/Game Room
1010 out of 10 rating
Exceptional
(16 reviews)
Relaxing 2800sf Countryside Bourbon Trail Home w/Game Room
Bloomfield, KY
8% off
Price is NZ$3,355
NZ$3,355
NZ$479 per night
includes taxes & fees
Image gallery for Luxurious Suite w/Garden on Court Square Downtown
1010 out of 10 rating
Exceptional
(116 reviews)
Luxurious Suite w/Garden on Court Square Downtown
Bardstown, KY
8% off
Price is NZ$2,094
NZ$2,094
NZ$299 per night
includes taxes & fees
Image gallery for Cozy 3 bedroom in country , close to town
1010 out of 10 rating
Exceptional
(12 reviews)
Cozy 3 bedroom in country , close to town
Bardstown, KY
8% off
Price is NZ$4,079
NZ$4,079
NZ$583 per night
includes taxes & fees
Image gallery for Bourbon Cottage, 2 BR, Downtown Historic Bardstown next to Bakery!
1010 out of 10 rating
Exceptional
(80 reviews)
Bourbon Cottage, 2 BR, Downtown Historic Bardstown next to Bakery!
Bardstown, KY
8% off
Price is NZ$2,773
NZ$2,773
NZ$396 per night
includes taxes & fees
Image gallery for Classic Kentucky Farm: Bluegrass - Bourbon - PGA -Firepit-Horse Country-WiFi
1010 out of 10 rating
Exceptional
(45 reviews)
Classic Kentucky Farm: Bluegrass - Bourbon - PGA -Firepit-Horse Country-WiFi
Taylorsville, KY
12% off
Price is NZ$7,212
NZ$7,212
NZ$1,030 per night
includes taxes & fees
Image gallery for Welcome to your home away from home at my Bardstown’s Sweet Retreat!
1010 out of 10 rating
Exceptional
(73 reviews)
Welcome to your home away from home at my Bardstown’s Sweet Retreat!
Bardstown, KY
15% off
Price is NZ$2,253
NZ$2,253
NZ$322 per night
includes taxes & fees
Image gallery for ⭐Lake side cottage✦Gated community✦community pool✦private hot tub✦nearby golf course✦nearby frisbee golf course✦nearby Marina✦nearby liquor stores⭐
9.69.6 out of 10 rating
Exceptional
(44 reviews)
⭐Lake side cottage✦Gated community✦community pool✦private hot tub✦nearby golf course✦nearby frisbee golf course✦nearby Marina✦nearby liquor stores⭐
Taylorsville, KY
8% off
Price is NZ$3,149
NZ$3,149
NZ$450 per night
includes taxes & fees
Image gallery for CABIN GET AWAY SECLUDED bourbon trail! Kentucky at its best !
1010 out of 10 rating
Exceptional
(12 reviews)
CABIN GET AWAY SECLUDED bourbon trail! Kentucky at its best !
Willisburg, KY
8% off
Price is NZ$2,991
NZ$2,991
NZ$427 per night
includes taxes & fees
Image gallery for KY Derby - Fire pit - Foosball - KY Bourbon Trail
1010 out of 10 rating
Exceptional
(29 reviews)
KY Derby - Fire pit - Foosball - KY Bourbon Trail
Bardstown, KY
8% off
Price is NZ$3,786
NZ$3,786
NZ$541 per night
includes taxes & fees
Image gallery for McIntyre’s Country Getaway
1010 out of 10 rating
Exceptional
(6 reviews)
McIntyre’s Country Getaway
Bardstown, KY
8% off
Price is NZ$3,836
NZ$3,836
NZ$548 per night
includes taxes & fees
Image gallery for John Fitch Cottage, 1BR - Patio - Downtown
9.89.8 out of 10 rating
Exceptional
(98 reviews)
John Fitch Cottage, 1BR - Patio - Downtown
Bardstown, KY
8% off
Price is NZ$2,376
NZ$2,376
NZ$339 per night
includes taxes & fees
Image gallery for Belle Beam Room-easy walk to downtown & 10mins to distilleries-NO Cleaning Fee!
1010 out of 10 rating
Exceptional
(5 reviews)
Belle Beam Room-easy walk to downtown & 10mins to distilleries-NO Cleaning Fee!
Bardstown, KY
8% off
Price is NZ$1,541
NZ$1,541
NZ$220 per night
includes taxes & fees
Image gallery for Unique Woodland Haven: Peaceful Historic Cabin with Modern Comforts
9.89.8 out of 10 rating
Exceptional
(33 reviews)
Unique Woodland Haven: Peaceful Historic Cabin with Modern Comforts
Shepherdsville, KY
16% off
Price is NZ$2,439
NZ$2,439
NZ$348 per night
includes taxes & fees
Image gallery for Pioneer Park Cottage, 2 BR/2 BA Downtown Historic Bardstown
1010 out of 10 rating
Exceptional
(110 reviews)
Pioneer Park Cottage, 2 BR/2 BA Downtown Historic Bardstown
Bardstown, KY
8% off
Price is NZ$2,952
NZ$2,952
NZ$422 per night
includes taxes & fees
Image gallery for Seabiscuit 5- Relax And Kick Back
9.69.6 out of 10 rating
Exceptional
(50 reviews)
Seabiscuit 5- Relax And Kick Back
Taylorsville, KY
8% off
Price is NZ$2,625
NZ$2,625
NZ$375 per night
includes taxes & fees
Image gallery for Foster & 5th / 3 BDRM Downtown Historical Colonial
9.89.8 out of 10 rating
Exceptional
(41 reviews)
Foster & 5th / 3 BDRM Downtown Historical Colonial
Bardstown, KY
8% off
Price is NZ$3,928
NZ$3,928
NZ$561 per night
includes taxes & fees
Image gallery for Bardstown Bourbon Trail House
9.89.8 out of 10 rating
Exceptional
(79 reviews)
Bardstown Bourbon Trail House
Bardstown, KY
8% off
Price is NZ$2,545
NZ$2,545
NZ$364 per night
includes taxes & fees
Image gallery for Bourbon Belle of Bardstown - Charming home just a 9 minute walk into downtown!
1010 out of 10 rating
Exceptional
(25 reviews)
Bourbon Belle of Bardstown - Charming home just a 9 minute walk into downtown!
Bardstown, KY
9% off
Price is NZ$2,630
NZ$2,630
NZ$376 per night
includes taxes & fees
Image gallery for Millstone Cottage, 2 BR/1 BA/Patio- Downtown
1010 out of 10 rating
Exceptional
(68 reviews)
Millstone Cottage, 2 BR/1 BA/Patio- Downtown
Bardstown, KY
8% off
Price is NZ$2,773
NZ$2,773
NZ$396 per night
includes taxes & fees
Image gallery for Kentucky Nights, Bourbon Flights/ Hot Tub+Firepit Fun
1010 out of 10 rating
Exceptional
(23 reviews)
Kentucky Nights, Bourbon Flights/ Hot Tub+Firepit Fun
Springfield, KY
9% off
Price is NZ$2,895
NZ$2,895
NZ$414 per night
includes taxes & fees
Image gallery for *NEW* Bourbon on Broadway- 3 King Bed- Downtown Bardstown
1010 out of 10 rating
Exceptional
(32 reviews)
*NEW* Bourbon on Broadway- 3 King Bed- Downtown Bardstown
Bardstown, KY
8% off
Price is NZ$4,611
NZ$4,611
NZ$659 per night
includes taxes & fees
Image gallery for "Cottage In The Rye" in the Bourbon Capital of the World
9.89.8 out of 10 rating
Exceptional
(98 reviews)
"Cottage In The Rye" in the Bourbon Capital of the World
Bardstown, KY
8% off
Price is NZ$3,288
NZ$3,288
NZ$470 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Chuckleberry Farm & Winery
Classic Kentucky Farm: Bluegrass - Bourbon - PGA -Firepit-Horse Country-WiFi
Sleeps 8 · 4 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
45 reviews(45 reviews)
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
209 reviews(209 reviews)
3B/3B; Single Family Lakeside Retreat W/Hot Tub
Sleeps 10 · 3 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
45 reviews(45 reviews)
Best View of Taylorville Lake My Perfect Place
Sleeps 7 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
59 reviews(59 reviews)
⭐Lake side cottage✦Gated community✦community pool✦private hot tub✦nearby golf course✦nearby frisbee golf course✦nearby Marina✦nearby liquor stores⭐
Sleeps 7 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
44 reviews(44 reviews)
Southern Lights 56- Brand NEW hot tub and deck!
Sleeps 9 · 3 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
28 reviews(28 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value