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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 47 Cottages in Crestwood with updated reviews, rates, and availability.

2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub
Interior

2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub

10.0 out of 10, Exceptional, (23)
"The location is perfect for horse races and distillery tours. With it being located in between Lexington and Louisville, it was perfect for day trips to places of interest. "
2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub
Spacious Prospect Cottage w/ Deck & Scenic Views
Interior

Spacious Prospect Cottage w/ Deck & Scenic Views

9.2 out of 10, Wonderful, (17)
"Place just worked for us"
Spacious Prospect Cottage w/ Deck & Scenic Views
2 Mi to Churchill Downs: Louisville Home!
Fridge, microwave, stovetop, dishwasher

2 Mi to Churchill Downs: Louisville Home!

8.8 out of 10, Excellent, (12)
"The location and residence met the needs of 4 adults. "
2 Mi to Churchill Downs: Louisville Home!
Beautiful restored Victorian farmhouse
Fridge, microwave, oven, stovetop

Beautiful restored Victorian farmhouse

9.2 out of 10, Wonderful, (11)
"This property was just as described. Communication with the host was excellent. We’ll stay here again!"
The price is AED 900
AED 1,753 total
includes taxes & fees
11 Jun - 12 Jun
Beautiful restored Victorian farmhouse
KY Bourbon Trail Home, King Bed, FirePit, Near Louisville
Fridge, microwave, oven, stovetop

KY Bourbon Trail Home, King Bed, FirePit, Near Louisville

9.8 out of 10, Exceptional, (7)
"The perfect location for a quick stop on the bourbon trail. Ten minutes from Bulleit, down the road from Jeptha Creed, and a short hop over to Buffalo Trace and downtown Louisville!"
The price is AED 492
AED 1,169 total
includes taxes & fees
3 Jun - 4 Jun
KY Bourbon Trail Home, King Bed, FirePit, Near Louisville
Pet-friendly Clarksville Home w/ Central A/C
House (3 Bedrooms) | Interior

Pet-friendly Clarksville Home w/ Central A/C

3.0 star property
Pet-friendly Clarksville Home w/ Central A/C
Cozy Home in Louisville: Near Bardstown Road!
House (3 Bedrooms) | Interior

Cozy Home in Louisville: Near Bardstown Road!

3.0 star property
Cozy Home in Louisville: Near Bardstown Road!
Pet-friendly Emerald Lake Retreat in Charlestown!
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Pet-friendly Emerald Lake Retreat in Charlestown!

3.0 star property
Pet-friendly Emerald Lake Retreat in Charlestown!
Pond-view Cabin Near Louisville on Racehorse Farm!
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Pond-view Cabin Near Louisville on Racehorse Farm!

3.0 star property
Pond-view Cabin Near Louisville on Racehorse Farm!
Shelbyville Home - On to the Bourbon Trail!
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Shelbyville Home - On to the Bourbon Trail!

3.0 star property
6.0 out of 10, (1)
Shelbyville Home - On to the Bourbon Trail!
La Grange Cabin on a Racehorse Farm w/ Pond Views!
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La Grange Cabin on a Racehorse Farm w/ Pond Views!

3.0 star property
La Grange Cabin on a Racehorse Farm w/ Pond Views!
Central & Dog-friendly Home in Louisville w/ Yard!
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Central & Dog-friendly Home in Louisville w/ Yard!

3.0 star property
Central & Dog-friendly Home in Louisville w/ Yard!
Spacious Prospect Cottage w/ Deck & Scenic Views
Interior

Spacious Prospect Cottage w/ Deck & Scenic Views

3.0 star property
Spacious Prospect Cottage w/ Deck & Scenic Views
Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill
Microwave, oven, stovetop, dishwasher

Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill

3.0 star property
10.0 out of 10, Exceptional, (1)
"Went for the view of the eclipse with friends. The home was Beautiful! Just as pictures detailed it. Took the fur baby along since it was offered, however left over from last dog droppings in yard and not enclosed yard. The home was perfect for the gathering of friends to mingle and share time/space. The fire pit was a plus factor for the day(chilly) but no fire wood was available without us having to cut our own from a falling tree on property or purchase it. The dishwasher hadn't been...
Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill
1 Mi to Downtown: New Albany Home w/ Yard
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1 Mi to Downtown: New Albany Home w/ Yard

3.0 star property
1 Mi to Downtown: New Albany Home w/ Yard
Contemporary Cottage with 2 HUGE COVERED PORCHES!
Private kitchen

Contemporary Cottage with 2 HUGE COVERED PORCHES!

Contemporary Cottage with 2 HUGE COVERED PORCHES!
Indiana Vacation Rental Near Downtown Louisville!
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Indiana Vacation Rental Near Downtown Louisville!

3.0 star property
Indiana Vacation Rental Near Downtown Louisville!
8 Mi to Louisville: New Albany Home w/ Grill!
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8 Mi to Louisville: New Albany Home w/ Grill!

3.0 star property
8 Mi to Louisville: New Albany Home w/ Grill!
Walk to Boat Ramp: Fenced Home in Jeffersonville!
House (4 Bedrooms) | Interior

Walk to Boat Ramp: Fenced Home in Jeffersonville!

3.0 star property
Walk to Boat Ramp: Fenced Home in Jeffersonville!
Louisville Area Home: Deck, Fire Pit, Creek!
Outdoor dining

Louisville Area Home: Deck, Fire Pit, Creek!

3.0 star property
Louisville Area Home: Deck, Fire Pit, Creek!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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