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Check prices for these dates

In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23

Browse Select Crestwood Vacation Homes

Our top choices for Crestwood vacation homes

Putt Putt House by Louisville Walking Bridge
Private kitchen

Putt Putt House by Louisville Walking Bridge

2.0 star property
10.0 out of 10, Exceptional, (8)
"Property was clean, well lit and very pretty. Location was near food, drink and activities, parking very accessible. Owner communicated promptly too. "
The price is CA $138
CA $407 total
includes taxes & fees
Sep 1 - Sep 2
Putt Putt House by Louisville Walking Bridge
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.
Fridge, microwave, oven, stovetop

Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.

10.0 out of 10, Exceptional, (26)
"We stopped for one night traveling through. The place was clean, easy to find, and close to a charming downtown. It was also close to many Louisville attractions. Rebecca was very quick to respond and was very communicative. "
The price is CA $99
CA $275 total
includes taxes & fees
Sep 2 - Sep 3
Relax, min from Louisville, Pet friendly, Entire house- fenced in backyard.
Charming 2br Hot Tub Getaway 2 Bedroom Home
House, 2 Bedrooms | Private kitchen

Charming 2br Hot Tub Getaway 2 Bedroom Home

3.5 star property
10.0 out of 10, Exceptional, (1)
"This is a quiet and cozy house with a gorgeous hot tub. It was close enough to Bowman Field without the hassle of traffic in Louisville. Highly recommend!"
The price is CA $253
CA $454 total
includes taxes & fees
Sep 14 - Sep 15
Charming 2br Hot Tub Getaway 2 Bedroom Home
"Oak & Barrel" #1 LOCATION in Louisville. Bourbon & Derby theme. Firepit.
Terrace/patio

"Oak & Barrel" #1 LOCATION in Louisville. Bourbon & Derby theme. Firepit.

10.0 out of 10, Exceptional, (7)
"Oak & Barrel was a great place to stay for a weekend on the Bourbon Trail. Close to downtown and well located for heading south to bourbon country. Rebecca was very responsive and the house was neat & tidy and well stocked. "
The price is CA $195
CA $485 total
includes taxes & fees
Sep 1 - Sep 2
"Oak & Barrel" #1 LOCATION in Louisville. Bourbon & Derby theme. Firepit.
Cozy Home | Just Steps Away from Churchill Downs!
Fridge, microwave, oven, stovetop

Cozy Home | Just Steps Away from Churchill Downs!

2.0 star property
7.4 out of 10, Good, (3)
"Very nice "
The price is CA $85
CA $305 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Home | Just Steps Away from Churchill Downs!
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
3 bedrooms, travel crib, free WiFi, bed sheets

Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

9.4 out of 10, Exceptional, (30)
"This location was great. House worked for us for the week we were in KY for the bourbon trail. Any issue we had while we were there the property owner corrected. "
The price is CA $172
CA $346 total
includes taxes & fees
Sep 1 - Sep 2
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
Outdoor spa tub

Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

10.0 out of 10, Exceptional, (16)
"While property is a bit off the beaten path, an absolute lovely property and host was ultra responsive!! We will be going back!"
The price is CA $253
CA $684 total
includes taxes & fees
Sep 1 - Sep 2
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
DerbyCity Getaway | Hot Tub | Near Churchill Downs
Terrace/patio

DerbyCity Getaway | Hot Tub | Near Churchill Downs

8.4 out of 10, Very good, (6)
"Loved the backyard "
The price is CA $114
CA $281 total
includes taxes & fees
Sep 8 - Sep 9
DerbyCity Getaway | Hot Tub | Near Churchill Downs
+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
Fridge, microwave, oven, stovetop

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

9.6 out of 10, Exceptional, (74)
"Great location, 10-15 minute Uber ride to Louisville."
The price is CA $265
CA $559 total
includes taxes & fees
Sep 1 - Sep 2
+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
Cozy open floor plan
Fridge, microwave, oven, stovetop

Cozy open floor plan

2.0 star property
The price is CA $191
CA $445 total
includes taxes & fees
Aug 31 - Sep 1
Cozy open floor plan
The Chestnut - Nulu
Terrace/patio

The Chestnut - Nulu

2.0 star property
9.8 out of 10, Exceptional, (22)
"We stayed here for a "
The price is CA $109
CA $278 total
includes taxes & fees
Sep 15 - Sep 16
The Chestnut - Nulu
NEW Hot Tub, Expo, King Beds, Downtown, Churchill
Terrace/patio

NEW Hot Tub, Expo, King Beds, Downtown, Churchill

9.8 out of 10, Exceptional, (77)
"Great property! Perfect for the five couples! House was very cute and relaxing! Plenty of space for all 10 of us!"
The price is CA $327
CA $955 total
includes taxes & fees
Sep 1 - Sep 2
NEW Hot Tub, Expo, King Beds, Downtown, Churchill
Charming 1920’s shotgun in southern Indiana, minutes from downtown Louisville
Property grounds

Charming 1920’s shotgun in southern Indiana, minutes from downtown Louisville

9.6 out of 10, Exceptional, (18)
"Enjoyed this quiet and comfortable spot in New Albany. Very tranquil and clean home. "
The price is CA $121
CA $269 total
includes taxes & fees
Sep 1 - Sep 2
Charming 1920’s shotgun in southern Indiana, minutes from downtown Louisville
Bourbon Trail Getaway ~ Hot Tub + Dogs Welcome + Game Room + Cornhole + KY Fun
Fridge, microwave, oven, stovetop

Bourbon Trail Getaway ~ Hot Tub + Dogs Welcome + Game Room + Cornhole + KY Fun

9.8 out of 10, Exceptional, (13)
"Very convenient to Louisville, Frankfort and Lexington. "
The price is CA $243
CA $608 total
includes taxes & fees
Sep 2 - Sep 3
Bourbon Trail Getaway ~ Hot Tub + Dogs Welcome + Game Room + Cornhole + KY Fun
Close to Expo Ctr, UofL, Walk to bars, shops!
Fridge, microwave, oven, stovetop

Close to Expo Ctr, UofL, Walk to bars, shops!

10.0 out of 10, Exceptional, (65)
"Lovely property in a nice neighborhood that reminded us of Soulard in STL"
The price is CA $111
CA $273 total
includes taxes & fees
Sep 1 - Sep 2
Close to Expo Ctr, UofL, Walk to bars, shops!
Historic 4 BR 3-1/2 BA Brick Home Old Louisville | Near Downtown Expo Derby UL
Terrace/patio

Historic 4 BR 3-1/2 BA Brick Home Old Louisville | Near Downtown Expo Derby UL

2.0 star property
10.0 out of 10, Exceptional, (1)
"It's a lovely, spacious house in a good location. On street parking isn't an issue as it's at the end of a dead-end (gated actually) street. But take note of the orange street sweeping signs. They aren't kidding about cars being towed on Thursdays.Everything we needed and a short walk to 610 Magnolia. Edward Lee is a genius with food."
The price is CA $182
CA $684 total
includes taxes & fees
Sep 1 - Sep 2
Historic 4 BR 3-1/2 BA Brick Home Old Louisville | Near Downtown Expo Derby UL
Chic Downtown King Suite~Free Parking~A+ Location
Living area

Chic Downtown King Suite~Free Parking~A+ Location

9.0 out of 10, Wonderful, (2)
"This place was absolutely perfect for us. It was within a few blocks of several distilleries. "
The price is CA $117
CA $287 total
includes taxes & fees
Sep 1 - Sep 2
Chic Downtown King Suite~Free Parking~A+ Location
3-BR First Floor Home Near Louisville Attractions
Game room

3-BR First Floor Home Near Louisville Attractions

2.0 star property
8.0 out of 10, Very good, (1)
"Excellent property, quiet and enjoyable"
The price is CA $172
CA $412 total
includes taxes & fees
Sep 1 - Sep 2
3-BR First Floor Home Near Louisville Attractions
The Caldwell - Germantown Highlands
Fridge, microwave, oven, stovetop

The Caldwell - Germantown Highlands

10.0 out of 10, Exceptional, (30)
"Nice house for our weekend stay. We would book again! "
The price is CA $98
CA $265 total
includes taxes & fees
Sep 1 - Sep 2
The Caldwell - Germantown Highlands
*Fun for All *LUX Hot Tub *Fire Pit *Games Galore
Terrace/patio

*Fun for All *LUX Hot Tub *Fire Pit *Games Galore

10.0 out of 10, Exceptional, (18)
"This is a very remote property, but it was comfortable and a fun place to relax after visiting distilleries. If you're looking to be away from everything, this is the place for you."
The price is CA $303
CA $885 total
includes taxes & fees
Sep 23 - Sep 24
*Fun for All *LUX Hot Tub *Fire Pit *Games Galore
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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Top Crestwood Hotel Reviews

Find out more about Crestwood

Find out more about Crestwood

Crestwood Vacation Homes information

Number of reviews
23
Accommodation
1026 Vacation Homes
Lowest Price
CA $98
Highest Price
CA $279

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