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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 45 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, (21)
"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
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!
La Grange Cabin on a Racehorse Farm w/ Pond Views!
Interior

La Grange Cabin on a Racehorse Farm w/ Pond Views!

3.0 star property
La Grange Cabin on a Racehorse Farm w/ Pond Views!
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!"
KY Bourbon Trail Home, King Bed, FirePit, Near Louisville
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
5 May - 6 May
Beautiful restored Victorian farmhouse
Spacious Prospect Cottage w/ Deck & Scenic Views
Interior

Spacious Prospect Cottage w/ Deck & Scenic Views

9.2 out of 10, Wonderful, (16)
"Place just worked for us"
Spacious Prospect Cottage w/ Deck & Scenic Views
Central & Dog-friendly Home in Louisville w/ Yard!
Interior

Central & Dog-friendly Home in Louisville w/ Yard!

3.0 star property
Central & Dog-friendly Home in Louisville w/ Yard!
Bright New Albany Home: 12 Mi to Churchill Downs!
Interior

Bright New Albany Home: 12 Mi to Churchill Downs!

3.0 star property
Bright New Albany Home: 12 Mi to Churchill Downs!
8 Mi to Louisville: New Albany Home w/ Grill!
Interior

8 Mi to Louisville: New Albany Home w/ Grill!

3.0 star property
8 Mi to Louisville: New Albany Home w/ Grill!
Shelbyville Home - On to the Bourbon Trail!
Interior

Shelbyville Home - On to the Bourbon Trail!

3.0 star property
6.0 out of 10, (1)
Shelbyville Home - On to the Bourbon Trail!
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!
Interior

Indiana Vacation Rental Near Downtown Louisville!

3.0 star property
Indiana Vacation Rental Near Downtown Louisville!
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 Clarksville Home w/ Central A/C
Terrace/patio

Pet-friendly Clarksville Home w/ Central A/C

3.0 star property
Pet-friendly Clarksville Home w/ Central A/C
1 Mi to Downtown: New Albany Home w/ Yard
Interior

1 Mi to Downtown: New Albany Home w/ Yard

3.0 star property
1 Mi to Downtown: New Albany Home 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
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!
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
Pet-friendly Emerald Lake Retreat in Charlestown!
Interior

Pet-friendly Emerald Lake Retreat in Charlestown!

3.0 star property
Pet-friendly Emerald Lake Retreat in Charlestown!
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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Other property types in Crestwood

Hancock House
Executive Room | View from room

Hancock House

3.0 star property
8.0 out of 10, Very Good, (232)
"Great stay!"
The price is AED 364
AED 764 total
includes taxes & fees
6 May - 7 May
Hancock House
Stellar Suites
Front of property

Stellar Suites

4.5 star property
9.6 out of 10, Exceptional, (93)
"Great location! Excellent dining options nearby!"
The price is AED 430
AED 691 total
includes taxes & fees
5 May - 6 May
Stellar Suites
The Bellwether Hotel
Highland Station Penthouse Suite | Private kitchen | Microwave, coffee/tea maker, paper towels

The Bellwether Hotel

2.0 star property
8.4 out of 10, Very Good, (13)
"The boutique Bellwether Hotel is so beautiful and a step back in time. The art deco design, the second floor lounge, and the rooms all beautifully decorated and comfortable. Walk to restaurants, grocery, bars and antique shops. "
The price is AED 537
AED 624 total
includes taxes & fees
27 May - 28 May
The Bellwether Hotel
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.