Bespoke Usa Travel - Vacation Rentals in Crestwood

Enchanting, energizing, and enjoyable! From US $280
         

10.0 (92 Reviews)
House
  • Air Conditioner
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  • TV
Pet-Friendly Louisville Escape about 15 Mi to Downtown From US $214
         

Residence Inn by Marriott Louisville Old Henry From US $200
         

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9.6 (284 Reviews)
Hotel
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  • Pool
The Persimmon Ridge Lodge - Golf Room & Pickleball! From US $729
         

NYE Getaway! Hot Tub, Game Rooms, 20 min to Lou From US $995
         

10.0 (18 Reviews)
House
  • Air Conditioner
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  • Pet Friendly
The Sweet Retreat Wheelchair Accessible Historic Home From US $277
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Crestwood

Over 81+ Luxury Places to Stay in or Near Crestwood
Luxury Living, Derby Thrills From US $11,617
         

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Kentucky Derby Entertainer's Paradise. From US $3,529
         

10.0 (1 Review)
House
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  • Pool
Derby Getaway: Spacious 6 Bed, Walkout Basement From US $3,322
         

Attention Derby visitors . 5,000 Sq Ft, 5 Bedroom, 41/2 baths. From US $2,913
         

Beautiful home with pool & home gym! Just 20 min to KY Derby! From US $1,999
         

10.0 (1 Review)
House
  • Air Conditioner
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  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Crestwood

Over 19+ Top-Rated Vacation Rentals with a Pool in or Near Crestwood
Derby 6 Bedroom House Rental with Private Pool From US $1,587
         

10.0 (18 Reviews)
House
  • Air Conditioner
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  • Pool
Holiday Inn Express & Suites La Grange by IHG From US $111
         

9.0 (766 Reviews)
Hotel
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  • Pool
Holiday Inn Express & Suites - La Grange by IHG From US $112
         

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8.7 (222 Reviews)
Hotel
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Holiday Inn Express Louisville Northeast by IHG From US $103
         

8.6 (613 Reviews)
Hotel
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  • Pool
La Quinta Inn & Suites by Wyndham Louisville NE/Old Henry Rd From US $98
         

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8.4 (917 Reviews)
Hotel
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  • Pet Friendly
Holiday Inn Express Louisville Northeast by IHG From US $108
         

8.3 (85 Reviews)
Hotel
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  • Pool
La Quinta Inn & Suites by Wyndham Louisville NE - Old Henry Rd From US $140
         

8.1 (300 Reviews)
Hotel
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  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Crestwood

Over 16+ Pet-Friendly Vacation Rentals in or Near Crestwood
Holiday Getaway ~ Hot Tub + Family-Friendly From US $340
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Sweet Retreat Accessible Historic Home From US $207
         

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9.8 (6 Reviews)
House
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  • Pet Friendly
12 Guest/Top Area/Families/Park From US $327
         

9.0 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Family & Dog Friendly Stay 15 mins to St. Matthews From US $316
         

7.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
NEW- 2Kings+HotTub+FirePit From US $769
         

10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • TV
Remodeled 50s Home in Quaint Downtown LaGrange From US $265
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Crestwood

Over 23+ Large Vacation Homes & Villas in or Near Crestwood
Spacious 5-bedroom house with pool! Sleeps 11 From US $943
         

New
House
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety
Relax and enjoy Golden Retreat while in town for the Kentucky Derby Festivities. From US $2,032
         

Wheelchair Accessible Vacation Homes in Crestwood

Over 5+ Wheelchair Accessible Vacation Homes in or Near Crestwood
Comfort Inn & Suites La Grange - Louisville Area From US $89
         

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7.0 (175 Reviews)
Hotel
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  • Pet Friendly
Best Western Ashbury Inn From US $91
         

8.2 (991 Reviews)
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  • Parking
  • TV
Super 8 by Wyndham La Grange KY From US $73
         

6.9 (258 Reviews)
Hotel
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  • Parking
  • Pet Friendly
Super 8 by Wyndham La Grange KY From US $84
         

7.0 (663 Reviews)
Hotel
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  • Parking
  • Wheelchair Accessible
Spark by Hilton La Grange From US $81
         

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7.6 (11 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Crestwood Varoom and Airbnb Places to Stay Under $200

Over 12+ Crestwood Varoom and Airbnb Places to Stay Under $200
Lagrange Loft - Small Town USA - Bourbon Trail From US $149
         

9.8 (26 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Residence Inn by Marriott Louisville Old Henry From US $143
         

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9.3 (100 Reviews)
Hotel
  • Security/Safety
  • Child Friendly
Derby City Hideaway From US $145
         

8.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • TV
Back Room Bungalow - Lagrange From US $149
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Crestwood Apartment w/Pool Table! From US $165
         

8.8 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Cozy, 2 story townhouse Putting green and playroom. From US $180
         

Cozy Louisville Apt w/ Patio, Fire Pit & Game Room From US $98
         

Instantly Bookable Vacation Homes in Crestwood

Over 14+ Instantly Bookable Vacation Homes in or Near Crestwood
Briar Creek Cottage From US $250
         

New
Cottage
  • Air Conditioner
  • Parking
  • TV
5-acre Estate Home w/Swimming Pool, 10 minutes to Valhalla! From US $2,500
         

2024 KY Derby Golf Community Home From US $2,000
         

New
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Spacious Home with Scenic Views Near Valhalla & Churchill Downs From US $1,900
         

About Crestwood Vacation Rentals

With more than 90 Crestwood vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Bespokeusatravel and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Crestwood.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Bespokeusatravel Crestwood, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Crestwood. Places to stay near Crestwood are 1336.54 ft² on average, with prices averaging $1,231 a night.

Bespokeusatravel makes it easy and safe to find and compare vacation rentals in Crestwood with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Crestwood

Type Count
Vacation Homes 61
Hotels with Suites 16
Holiday Apartments 4
Cottages 3
Others 3
Cabin Rentals 2

Use these Quick Filters to Find a Vacation Rental in Crestwood

Pro Tip: Bespokeusatravel makes it easy to compare the best listings on Bespokeusatravel homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Bespokeusatravel homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Crestwood.

Weather in Crestwood

View the weather forecast for Crestwood before booking your Crestwood Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F