Holiday rentals near Chuckleberry Farm & Winery
We found 189 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:8 Aug - 15 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$3,659
NZ$3,659
NZ$523 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$3,327
NZ$3,327
NZ$475 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$4,830
NZ$4,830
NZ$690 per night
includes taxes & fees
Image gallery for CABIN GET AWAY SECLUDED bourbon trail! Kentucky at its best !
1010 out of 10 rating
Exceptional
(13 reviews)
CABIN GET AWAY SECLUDED bourbon trail! Kentucky at its best !
Willisburg, KY
8% off
Price is NZ$2,965
NZ$2,965
NZ$424 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$2,750
NZ$2,750
NZ$393 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$4,045
NZ$4,045
NZ$578 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$2,076
NZ$2,076
NZ$297 per night
includes taxes & fees
Image gallery for Classic Kentucky Farm: Bluegrass - Bourbon - PGA -Firepit-Horse Country-WiFi
1010 out of 10 rating
Exceptional
(46 reviews)
Classic Kentucky Farm: Bluegrass - Bourbon - PGA -Firepit-Horse Country-WiFi
Taylorsville, KY
12% off
Price is NZ$6,546
NZ$6,546
NZ$935 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$3,106
NZ$3,106
NZ$444 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$2,234
NZ$2,234
NZ$319 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$2,855
NZ$2,855
NZ$408 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$3,804
NZ$3,804
NZ$543 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$1,528
NZ$1,528
NZ$218 per night
includes taxes & fees
Image gallery for John Fitch Cottage, 1BR - Patio - Downtown
9.89.8 out of 10 rating
Exceptional
(99 reviews)
John Fitch Cottage, 1BR - Patio - Downtown
Bardstown, KY
8% off
Price is NZ$2,356
NZ$2,356
NZ$337 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
(34 reviews)
Unique Woodland Haven: Peaceful Historic Cabin with Modern Comforts
Shepherdsville, KY
16% off
Price is NZ$2,274
NZ$2,274
NZ$325 per night
includes taxes & fees
Image gallery for Stay downtown within walking distance of restaurants, shopping, and breweries!
9.69.6 out of 10 rating
Exceptional
(68 reviews)
Stay downtown within walking distance of restaurants, shopping, and breweries!
Bardstown, KY
8% off
Price is NZ$1,917
NZ$1,917
NZ$274 per night
includes taxes & fees
Image gallery for LARGE BARN WITH LIVING AREA Bourbon trail Keenland close,
1010 out of 10 rating
Exceptional
(11 reviews)
LARGE BARN WITH LIVING AREA Bourbon trail Keenland close,
Willisburg, KY
8% off
Price is NZ$3,319
NZ$3,319
NZ$474 per night
includes taxes & fees
Image gallery for Newly remodeled, Grigsby House in Historic Bardstown
1010 out of 10 rating
Exceptional
(77 reviews)
Newly remodeled, Grigsby House in Historic Bardstown
Bardstown, KY
8% off
Price is NZ$3,779
NZ$3,779
NZ$540 per night
includes taxes & fees
Image gallery for Bourbon, Bonfires& Bad Decisions-Book Your Getaway
1010 out of 10 rating
Exceptional
(23 reviews)
Bourbon, Bonfires& Bad Decisions-Book Your Getaway
Springfield, KY
9% off
Price is NZ$3,056
NZ$3,056
NZ$437 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$2,750
NZ$2,750
NZ$393 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$2,690
NZ$2,690
NZ$384 per night
includes taxes & fees
Image gallery for Country Cottage on the Bourbon Trail, near Bardstown, Peaceful, Family, Couples
1010 out of 10 rating
Exceptional
(7 reviews)
Country Cottage on the Bourbon Trail, near Bardstown, Peaceful, Family, Couples
Springfield, KY
12% off
Price is NZ$3,570
NZ$3,570
NZ$510 per night
includes taxes & fees
Image gallery for NEW “ Sweet SouthernComfort” 3 bd 2+bth. IN TOWN
1010 out of 10 rating
Exceptional
(5 reviews)
NEW “ Sweet SouthernComfort” 3 bd 2+bth. IN TOWN
Bardstown, KY
8% off
Price is NZ$3,713
NZ$3,713
NZ$530 per night
includes taxes & fees
Image gallery for A Romantic Getaway on the Bourbon Trail
1010 out of 10 rating
Exceptional
(47 reviews)
A Romantic Getaway on the Bourbon Trail
Willisburg, KY
22% off
Price is NZ$2,386
NZ$2,386
NZ$341 per night
includes taxes & fees
Find spaces that suit your style
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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
46 reviews(46 reviews)
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
211 reviews(211 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)
LogCabin-15 min Bardstown Pool
Sleeps 12 · 6 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
12 reviews(12 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