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Compare 790 Vacation Homes in Crestwood with updated reviews, rates, and availability.

☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT

☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT

9.0 out of 10, Wonderful, (20)
"Wonderful set up for our ladies weekend. Tyler was easy to work with and very responsive. Jeffersonville is a hidden gem!"
☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT
Historic District Townhouse in City's BEST Location
Interior

Historic District Townhouse in City's BEST Location

9.8 out of 10, Exceptional, (185)
"This was a great stay and the property was so well-managed! Super easy to check in, everything was in great condition. Comfortable beds, and pretty much anything you need in the kitchen. The property was spotless. They provide white noise machines to mask outdoor noises, since it's on a commercial strip, but we didn't need them. Just note that you do need to climb stairs to get to the bedrooms. Deirdre was super-responsive to questions. Highly recommend."
Historic District Townhouse in City's BEST Location
River City Retreat near Zoo/Expo/Airport/Churchill + Arcade
Interior detail

River City Retreat near Zoo/Expo/Airport/Churchill + Arcade

9.8 out of 10, Exceptional, (50)
"Close to the Expo for the livestock show stay. House was clean. Beds were comfortably. "
River City Retreat near Zoo/Expo/Airport/Churchill + Arcade
The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands
Original stained glass windows adorn your expansive living area!

The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands

10.0 out of 10, Exceptional, (137)
"Stayed for a few nights with family over Thanksgiving. Communication with James was outstanding. The house is exactly as pictured, which means it is interesting and beautiful, combining modern comforts with original beauty. Neighborhood could not have been better - quiet but with extremely easy walking access to a ton of stuff. Highly recommend!"
The price is AED 687
AED 1,441 total
includes taxes & fees
30 Dec - 31 Dec
The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands
Near Highways and a 20 Min Drive to Louisville's Main Attractions
Open floor plan with lots of light.

Near Highways and a 20 Min Drive to Louisville's Main Attractions

10.0 out of 10, Exceptional, (33)
"The house was a great location for doing a lot of the distilleries. With my big group we had no problems with places to sleep and hang out. A+++"
Near Highways and a 20 Min Drive to Louisville's Main Attractions
Newly Renovated Studio! Ideal location for walking to restaurants & shops
1,000 sq foot studio. Fully renovated with new furniture, appliances, etc

Newly Renovated Studio! Ideal location for walking to restaurants & shops

9.8 out of 10, Exceptional, (23)
"Place was very clean and cozy. Easy to get in and out and owner was very responsive. "
Newly Renovated Studio! Ideal location for walking to restaurants & shops
Luxurious home in centrally located Phoenix Hill. Mins to NULU & Bourbon Trail
Enjoy a meal on the deck or play games in the massive backyard. There's plenty of room to get a game of Cornhole going.

Luxurious home in centrally located Phoenix Hill. Mins to NULU & Bourbon Trail

9.8 out of 10, Exceptional, (26)
"Property was clean and had amenities we needed. Great place to stay as a starting point to other points of interest. Needed to be careful where you went in some surrounding neighborhoods."
The price is AED 279
AED 999 total
includes taxes & fees
7 Jan - 8 January 2025
Luxurious home in centrally located Phoenix Hill. Mins to NULU & Bourbon Trail
Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill
Shelbyville Vacation Rental | 3BR | 2BA | 1,700 Sq Ft | Steps Required to Access

Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill

9.8 out of 10, Exceptional, (11)
"There are a few issues with the listing and the property. Very happy overall with our stay. However, second bathroom door does not latch. No heat register in the second bathroom which makes it very cold. Master bedroom door does not latch. Grounds were not kept up very well. Extensions cords laying across the back sidewalk. Yard is NOT fenced in like the description indicates. We loved the location and the overall layout of the house, just needs some attention. "
Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill
Derby Cigar & Bourbon Lounge Group Stays in charming Louisville
Exterior detail

Derby Cigar & Bourbon Lounge Group Stays in charming Louisville

The price is AED 694
AED 2,004 total
includes taxes & fees
29 Dec - 30 Dec
Derby Cigar & Bourbon Lounge Group Stays in charming Louisville
10 Min to Louisville, Huge Hot Tub, Awesome Backyard
Terrace/patio

10 Min to Louisville, Huge Hot Tub, Awesome Backyard

10.0 out of 10, Exceptional, (25)
"Quality family time. Spacious space. inviting "
10 Min to Louisville, Huge Hot Tub, Awesome Backyard
The Trifecta in Old Louisville
Historic Victorian Home circa 1890s

The Trifecta in Old Louisville

10.0 out of 10, Exceptional, (109)
"House is exactly as advertised. Host very responsive and accommodating. Nice location. We had a great stay, thank you!"
The Trifecta in Old Louisville
Cozy Louisville Home w/ Spacious Yard & Parking
Living area

Cozy Louisville Home w/ Spacious Yard & Parking

10.0 out of 10, Exceptional, (8)
"This little house is a hidden gem! I booked it as it was close to the U of L hospital where my husband was to have major surgery. It was absolutely perfect for my needs. I didn’t get to enjoy it much as I was mainly just there to shower and catch a little sleep. The houses along this street are cute and well maintained. I felt safe there even tho I was alone. There are some homes a few blocks away that are a little questionable, but the homes near here are adorable. I would definitely stay...
Cozy Louisville Home w/ Spacious Yard & Parking
7Br/4Ba - 4k Ft - Updated Gorgeous Historic Home

7Br/4Ba - 4k Ft - Updated Gorgeous Historic Home

10.0 out of 10, Exceptional, (15)
"Was in Louisville for a bachelor party (20 of us). The house was amazing! Plenty of space, very clean, great location. Would definitely recommend for larger groups."
7Br/4Ba - 4k Ft - Updated Gorgeous Historic Home
Stay at Bourbon Belle in Germantown for the Bourbon Trail, Churchill Downs! WiFi
Private kitchen

Stay at Bourbon Belle in Germantown for the Bourbon Trail, Churchill Downs! WiFi

10.0 out of 10, Exceptional, (59)
"Very nice. Beautifully decorated "
The price is AED 279
AED 746 total
includes taxes & fees
6 Jan - 7 January 2025
Stay at Bourbon Belle in Germantown for the Bourbon Trail, Churchill Downs! WiFi
5BR Very Spacious Home! Perfect for Family!
012

5BR Very Spacious Home! Perfect for Family!

8.8 out of 10, Excellent, (9)
"We had a great stay! Beautiful home in a safe and quiet neighborhood. Great communication with host. Comfortable accommodations for 10 adults. Easy access to Freedom Hall where our event was hosted."
The price is AED 327
AED 1,399 total
includes taxes & fees
30 Dec - 31 Dec
5BR Very Spacious Home! Perfect for Family!
Cozy, historic, pet-friendly home!
Living area

Cozy, historic, pet-friendly home!

9.8 out of 10, Exceptional, (14)
"The home is just as it appears in the photos....very charming and entertaining with seasonal decorations. The home was clean and comfortable. We enjoyed the gas firepit outside after touring the town. We will return during this season as the decorations for walking tours and historical site visits were amazing. Great location."
The price is AED 900
AED 1,432 total
includes taxes & fees
31 Dec - 1 January 2025
Cozy, historic, pet-friendly home!
Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City
Exterior

Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City

9.8 out of 10, Exceptional, (61)
"Really enjoyed the house, very spacious. Great host as well, would recommend staying here!"
The price is AED 2,384
AED 4,617 total
includes taxes & fees
1 Jan - 2 January 2025
Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City
Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!
Spring blooms!

Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!

9.8 out of 10, Exceptional, (80)
"The host of this property is great. She communicates well and was easily accessible. The property is clean and in a great location if you are looking for things south of Louisville. Great layout for families with kids and in-laws. "
The price is AED 551
AED 1,627 total
includes taxes & fees
6 Jan - 7 January 2025
Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!
The Orange Door ~ Prime Germantown 4BR/2BA Luxury
The Orange Door welcomes you to Louisville

The Orange Door ~ Prime Germantown 4BR/2BA Luxury

10.0 out of 10, Exceptional, (19)
"It was pretty solid no real complaints."
The price is AED 584
AED 1,457 total
includes taxes & fees
8 Jan - 9 January 2025
The Orange Door ~ Prime Germantown 4BR/2BA Luxury
The Curated Chateau—Minutes from Louisville
Exterior detail

The Curated Chateau—Minutes from Louisville

10.0 out of 10, Exceptional, (24)
"Wish it was warm enough to enjoy the backyard. Our daughter lives in Louisville. We came to visit her, and watch our 10 yo grandson swim at uofl. Also enjoyed lights under Louisville "
The Curated Chateau—Minutes from Louisville
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

Stellar Suites
Front of property

Stellar Suites

4.5 star property
9.6 out of 10, Exceptional, (89)
"Outstanding!"
The price is AED 490
AED 760 total
includes taxes & fees
10 Jan - 11 January 2025
Stellar Suites
Hancock House
Exterior

Hancock House

3.0 star property
8.0 out of 10, Very Good, (197)
"I was impressed with the room. It smelled nice, it was clean, and I really liked the design. They programmed a set of codes for me and they were easy to follow. I also felt like the parking was safe. I would definitely stay there again. "
The price is AED 312
AED 576 total
includes taxes & fees
5 Jan - 6 January 2025
Hancock House
A Cozy Cottage Near the Heart of All Louisville Attractions!
Outside view of Americas Barn

A Cozy Cottage Near the Heart of All Louisville Attractions!

10.0 out of 10, Exceptional, (341)
"Clean, sweet, comfortable with 🐔 chickens, deer 🦌in the back. Fresh eggs, along with other breakfast items were delicious. I’ll do it again if available. ☺️"
A Cozy Cottage Near the Heart of All Louisville Attractions!
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.