Vacation rentals in Crestwood

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Top-rated vacation rentals in Crestwood

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Guest favorite

Guest suite in Jeffersonville

4.93 out of 5 average rating, 150 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.

Feb 26 – Mar 5

$128 per night

Guest favorite

Guesthouse in Prospect

5.0 out of 5 average rating, 29 reviews

Prospect Guest House

Take it easy at this unique and tranquil getaway. Newly remodeled, new bathroom and kitchenette. We live in the house next door, but guest house is private and very quiet. Nestled in horse country - neighboring horses graze in adjacent fields. Queen bed upstairs, brand new sofas/pull out beds upstairs and downstairs. Lots of closet space, extra large bathtub, internet and streaming TV. Great location whether you are touring the Bourbon Trail or attending any of the The Kentucky Derby events!

Oct 14 – 21

$104 per night

Guest favorite

Guest suite in Louisville

4.93 out of 5 average rating, 209 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.

Dec 26 – Jan 2

$65 per night

Guest favorite

Home in Bedford

4.99 out of 5 average rating, 187 reviews

Atoka Farms

If you are looking to get away in seclusion and be with Mother Nature, this is the home. Very quiet, with a running creek beside the home. Walking distance to the Ohio river, two outdoor decks, one with a grill. A car port, full kitchen, two full baths, paved driveway, trees all around. The home sits between two hill ridges surrounded by 160 acres. It is a park like setting. 30 minutes from Gene Snyder and I-71 (Louisville). Historic Lagrange Ky and Madison In, are a must see and close by.

Dec 17 – 24

$119 per night

Guest favorite

Guest suite in Louisville

4.97 out of 5 average rating, 117 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!

Nov 6 – 13

$93 per night

Guest favorite

Tiny home in La Grange

4.97 out of 5 average rating, 158 reviews

Brakeman's Cottage

"All Aboard the Brakeman's Cottage! Experience the charm of this tiny house listed on the National Register of Historic Buildings in LaGrange, Kentucky. Nestled just feet from the train tracks in the heart of downtown, it offers a unique experience. Situated across from the train observation tower and within walking distance of the best restaurants and quaint shops, our newly remodeled property features private off-street parking. Step into history with modern comforts at Brakeman's

Nov 19 – 26

$85 per night

Superhost

Apartment in Pewee Valley

5.0 out of 5 average rating, 22 reviews

Loft in Pewee Valley

Welcome to our charming Pewee Valley loft! This tastefully decorated 2-bedroom, 1 bathroom space is an inviting retreat for your next getaway. Nestled in a peaceful town, it offers a perfect blend of comfort and serenity. Lounge in the cozy living area or enjoy a cup of coffee on the private balcony. Conveniently located near local attractions and with easy access to nearby cities, this hidden gem is ready to make your stay unforgettable. Book now and experience the charm firsthand!

Jun 10 – 17

$101 per night

Guest favorite

Home in Louisville

4.85 out of 5 average rating, 164 reviews

Private EAST END gem, minutes from everything!

Cozy, East End cottage just minutes from Top Golf, shopping malls, restaurants, entertainment, and other amenities. Easy access to the expressway. Home is well appointed with granite countertops, stainless appliances, hardwood floors, and more. A seasonal creek across from the house can be heard giving the impression of a cabin in the woods with privacy and seclusion, with the convenience of city living at your fingertips. There is also a beautiful park steps away from the house.

Jul 7 – 14

$68 per night

Guest favorite

Guest suite in Crestwood

4.95 out of 5 average rating, 61 reviews

Charming suite in Bourbon Country

A great base for bourbon tours, the Derby, Louisville and Central KY attractions. Easy access to I-71, 25 minutes from downtown Louisville. 5 minutes from distillery, brewery, and botanical gardens in scenic Oldham County. A beautiful spot off the beaten path to relax and recharge. Private two bedroom basement suite with natural light, dedicated entrance, and privacy. Shared outside covered deck and yard with mature trees. 1 queen, 2 twin beds, 1 queen air mattress.

Mar 17 – 24

$77 per night

Guest favorite

Guest suite in Prospect

4.97 out of 5 average rating, 169 reviews

Private Prospect Flat

Two bedroom apartment located on picturesque Covered Bridge Road in Prospect, KY. There is a separate entrance with plenty of parking. Beautiful views of Kentucky landscape from every window. Our property is four acres with a meandering stream, forest, and fields. There is a fully stocked kitchen including a dishwasher. The main bedroom includes a work space area and two closets. Feel free to grab a few eggs for breakfast if there are eggs in the nesting boxes.

May 30 – Jun 6

$123 per night

Guest favorite

Guesthouse in Louisville

4.97 out of 5 average rating, 112 reviews

The City Cottage…quiet, peaceful, and convenient!

A quaint, cozy, and private space close to everything Louisville has to offer. Located on the Northeast side of Louisville, The City Cottage is near the highways for quick access to destinations in and around Louisville. This newly completed space is fresh, clean and created for guests in mind. Are you a couple traveling or a business person wanting more room and comfort than a typical hotel? The City Cottage is for you! (Three night minimum during Derby time.)

May 25 – Jun 1

$119 per night

Guest favorite

Farm stay in Goshen

4.98 out of 5 average rating, 286 reviews

The Coop

This 2 bedroom house is a renovated old farmhouse located on the site of a small vegetable farm and native plant nursery. The back deck overlooks the woods, where you can watch the wild birds and keep an eye on the free range chickens. This is a quiet spot for a retreat, but also 25 minutes from downtown Louisville. The Coop has a fully stocked kitchen and comes with eggs right from our flock....

Nov 10 – 17

$99 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Crestwood vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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 favorite

Condo in La Grange

5.0 out of 5 average rating, 50 reviews

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

Aug 20 – 27

$121 per night

Guest favorite

Guest suite in Louisville

4.97 out of 5 average rating, 30 reviews

Middletown Private Guest House

Jun 21 – 28

$80 per night

Guest favorite

Guest suite in Shelbyville

4.97 out of 5 average rating, 33 reviews

Spacious suite, country views, pool table, firepit

Feb 14 – 21

$113 per night

Guest favorite

Home in La Grange

4.9 out of 5 average rating, 83 reviews

Little Blue Cottage on Main Street, La Grange KY

Jun 16 – 23

$133 per night

Guest favorite

Cottage in Jeffersonville

4.93 out of 5 average rating, 43 reviews

Peaceful Easy Feeling

Jul 23 – 30

$107 per night

Guest favorite

Guest suite in Louisville

4.88 out of 5 average rating, 34 reviews

Spacious one bedroom first floor suite

Sep 3 – 10

$83 per night

Guest favorite

Apartment in Charlestown

4.93 out of 5 average rating, 41 reviews

Cozy hideaway on Yankee creek.

Feb 22 – Mar 1

$96 per night

Guest favorite

Home in Jeffersonville

5.0 out of 5 average rating, 36 reviews

Beachfront River Cottage

Dec 15 – 22

$134 per night

Show all

Quick stats about vacation rentals in Crestwood

Total rentals	20 properties
Popular amenities	Gym, BBQ grill, and Laptop-friendly workspace
Wifi availability	20 properties include access to wifi
Family-friendly rentals	10 properties are a good fit for families
Total number of reviews	200 reviews
Nightly prices starting at	$50 before taxes and fees

Frequently Asked Questions

What are the most popular amenities for House Rentals in Crestwood?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in house rentals in Crestwood?
Experience the best of Crestwood with our house rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Crestwood have wireless internet?
Absolutely! We offer over 10 house rentals with wireless internet in Crestwood. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Crestwood?
Crestwood has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Vacation rentals in Crestwood

Top-rated vacation rentals in Crestwood

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Crestwood vacation rentals

Stay near Crestwood's top sights

Other great vacation rentals in Crestwood

Condo in La Grange

Guest suite in Louisville

Guest suite in Shelbyville

Home in La Grange

Cottage in Jeffersonville

Guest suite in Louisville

Apartment in Charlestown

Home in Jeffersonville

Quick stats about vacation rentals in Crestwood

Total rentals

Popular amenities

Wifi availability

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

What are the most popular amenities for House Rentals in Crestwood?

How much does it cost to stay in house rentals in Crestwood?

Do house rentals in Crestwood have wireless internet?

Are there family-friendly vacation rentals in Crestwood?

Destinations to explore