Vacation rentals in Crestwood

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Top-rated vacation rentals in Crestwood

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite

Guest suite in Jeffersonville

4.93 out of 5 average rating, 149 reviews

RIView 103. Modern Waterfront Suite Kentucky Derby

Guests can enjoy scenic views of the mighty Ohio River from any room in their private suite. Catch a beautiful sunrise or relax while sitting on the porch watching the boats and barges cruise the river. Close drive to interstate to get you to downtown Louisville to enjoy a dinner, museum, basketball game or concert in the KFC YUM Center and the world famous Churchill Downs! 1 mile away from River Ridge. We do offer a Tesla only charger or you can bring your own standard attachment for a charge.

Dec. 7 – 14

$234 CAD per night
Guest favourite

Guest suite in Louisville

4.93 out of 5 average rating, 205 reviews

Hide away close to everything

Recently remodeled in law suite. We just upgraded the bed to a queen size. Very private, detached garage getaway. A cozy sitting area 60" CableTV with HBO SHOWTIME and STARZ. Wet bar with fridge, ice maker, coffee maker, microwave, hot plate, dishes and some cookware. Private bath has shower and a walk in closet. This private apt. is above the garage. Outside has fenced in yard for your furry friend, outdoor fire pit and sitting area. Close to the interstate and minutes from downtown.

Aug. 28 – Sep. 4

$130 CAD per night
Guest favourite

Guest suite in Louisville

4.97 out of 5 average rating, 113 reviews

Derby City Hideaway

Whiskey Hollow offers you a unique stay with our Bourbon-themed space. Your stay in Kentucky is sure to be memorable and cozy. Our newly renovated space offers a full kitchen, cozy living area, bedroom and full bath with a private patio. Local attractions include Churchill Downs, home of the Kentucky Derby, Kentucky Derby Museum. Louisville Slugger Museum, Kentucky Bourbon Trail, local city eats, 4th Street Live, horse farms, hiking, waterfalls, parks, shopping, local arts, and much more!

Dec. 27 – Jan. 3

$170 CAD per night

Popular amenities for Crestwood vacation rentals

Stay near Crestwood's top sights

Yew Dell Botanical Gardens22 locals recommend
The Maples Park4 locals recommend
Cravings Byanca3 locals recommend
Rikishi4 locals recommend
3rd Turn Oldham Gardens10 locals recommend
Kentucky Artisan Distillery12 locals recommend

Other great vacation rentals in Crestwood

Guest favourite

Home in Bedford

4.99 out of 5 average rating, 185 reviews

Atoka Farms

Aug. 28 – Sep. 4

$224 CAD per night
Guest favourite

Cottage in Prospect

4.99 out of 5 average rating, 95 reviews

Cozy Cottage on Famous Kentucky Farm

Apr. 13 – 20

$348 CAD per night
Superhost

Loft in La Grange

4.92 out of 5 average rating, 36 reviews

Lagrange Loft - Small Town USA - Bourbon Trail

Feb. 20 – 27

$169 CAD per night
Guest favourite

Home in Crestwood

4.87 out of 5 average rating, 47 reviews

12 Guest/Top Area /Families/Park

Nov. 7 – 14

$447 CAD per night
Guest favourite

Farm stay in Shelbyville

5.0 out of 5 average rating, 30 reviews

Cozy Apartment at Red Gate Farm

Jun. 1 – 8

$150 CAD per night
Guest favourite

Condo in La Grange

5.0 out of 5 average rating, 48 reviews

The Beje (‘bay-hay’)-King Bed-Coffee Bar

Aug. 3 – 10

$235 CAD per night
Guest favourite

Guest suite in Louisville

4.88 out of 5 average rating, 33 reviews

Spacious one bedroom first floor suite

Sep. 9 – 16

$156 CAD per night
Guest favourite

Home in La Grange

4.9 out of 5 average rating, 80 reviews

Little Blue Cottage on Main Street, La Grange KY

Jul. 11 – 18

$256 CAD per night
Guest favourite

Home in Jeffersonville

5.0 out of 5 average rating, 33 reviews

Beachfront River Cottage

Nov. 28 – Dec. 5

$245 CAD per night
Guest favourite

Cottage in Jeffersonville

4.92 out of 5 average rating, 38 reviews

Peaceful Easy Feeling

Aug. 26 – Sep. 2

$206 CAD per night
Guest favourite

Guest suite in Shelbyville

4.97 out of 5 average rating, 33 reviews

Spacious suite, country views, pool table, firepit

Nov. 2 – 9

$192 CAD per night
Guest favourite

Home in La Grange

4.91 out of 5 average rating, 44 reviews

Caboose Cottage

Sep. 11 – 18

$233 CAD per night

Quick stats about vacation rentals in Crestwood

Total rentals

10 properties

Popular amenities

Gym, BBQ grill, and Laptop-friendly workspace

Wifi availability

10 properties include access to wifi

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

160 reviews

Nightly prices starting at

$68 CAD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Kentucky
  4. Oldham County
  5. Crestwood