Chicago\92s Best Vacation Rentals - Vacation Rentals in Chickasaw

Stylish Home Close to Derby & Bourbon Trail Fun From US $1,380
         

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10.0 (1 Review)
House
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The Pepin Mansion Historic B&B From US $106
         

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9.8 (693 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Family Friendly, Historic Mansion Row, *5 min from Louisville!* From US $1,209
         

10.0 (50 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
The Curated Chateau—Minutes from Louisville From US $239
         

Chic & Historic Apartment ~ 6 Mi to Louisville! From US $150
         

10.0 (14 Reviews)
Apartment
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Luxury Places to Stay in Chickasaw

Over 127+ Luxury Places to Stay in or Near Chickasaw
Spacious 8-BR Home Near Bourbon Trail Attractions! From US $1,254
         

9.6 (4 Reviews)
House
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Pink Pink Pink Brides&Besties From US $1,129
         

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New
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  • View
Classic & elegant Victorian home in Old Louisville From US $597
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • TV
  • Security/Safety

Top-Rated Vacation Rentals with a Pool in Chickasaw

Over 5+ Top-Rated Vacation Rentals with a Pool in or Near Chickasaw
Hampton Inn New Albany Louisville West From US $87
         

8.8 (814 Reviews)
Hotel
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  • Pool
Hampton Inn New Albany Louisville West From US $138
         

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8.7 (204 Reviews)
Hotel
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  • Pet Friendly
Holiday Inn Express - New Albany From US $120
         

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8.4 (489 Reviews)
Hotel
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  • Parking
  • Pool
Holiday Inn Express New Albany - Louisville NW by IHG From US $105
         

Elegant Room Near Local Attractions Free Wi-Fi From US $148
         

New
House
  • Pool
  • Wheelchair Accessible
  • Child Friendly

Pet-Friendly Vacation Rentals in Chickasaw

Over 19+ Pet-Friendly Vacation Rentals in or Near Chickasaw
The Perfect Spot in Downtown From US $157
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Derby City Getaway From US $204
         

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7.5 (59 Reviews)
Apartment
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  • Parking
  • Pet Friendly
Great for Derby & Events in Louisville/So Ind From US $150
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Dolphins Cove | Hot Tub | Near Churchill Downs 2 Bedroom From US $230
         

Deep Sea Diver | Hot Tub | Near Churchill Downs 3 Bedroom From US $313
         

Downtown Spot for Both Long & Short Term Stays From US $202
         

Large Vacation Homes & Villas in Chickasaw

Over 14+ Large Vacation Homes & Villas in or Near Chickasaw
The Pepin Mansion B&B on Mansion Row - 10 min to start of the Bourbon Trail From US $233
         

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9.4 (64 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Spacious brick home close to dining and nightlife! From US $285
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • TV
  • Security/Safety
Luxury Bourbon Trail & Derby Stay.n From US $377
         

10.0 (16 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Park View, Near Downtown, Attractions, WiFi From US $395
         

8.8 (6 Reviews)
House
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  • TV
  • Security/Safety
Shawnee Vacation Estate From US $221
         

6.0 (2 Reviews)
House
  • Air Conditioner
  • Designated Smoking Area
  • Bedding/Linens

Wheelchair Accessible Vacation Homes in Chickasaw

Over 4+ Wheelchair Accessible Vacation Homes in or Near Chickasaw
Museum Row’s Executive Loft From US $251
         

10.0 (3 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Days Inn & Suites by Wyndham Louisville SW From US $119
         

7.9 (285 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Days Inn & Suites by Wyndham Louisville SW From US $83
         

8.0 (444 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
The Derby (Downtown Louisville) From US $281
         

Chickasaw Vacation Rentals and Airbnb Places to Stay Under $200

Over 51+ Chickasaw Vacation Rentals and Airbnb Places to Stay Under $200
Cozy hideaway on Mason Row Main St. New Albany 10 minutes to downtown Louisville From US $114
         

Historic New Albany Apartment ~ 6 Mi to Louisville From US $174
         

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10.0 (1 Review)
Apartment
  • Parking
  • Security/Safety
  • Sports/Activities
Spacious unit close to Downtown business centers From US $161
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Historic New Albany Apartment ~ 6 Mi to Louisville From US $146
         

Modern Condo in Louisville From US $168
         

Instantly Bookable Vacation Homes in Chickasaw

Over 44+ Instantly Bookable Vacation Homes in or Near Chickasaw
Urban Gem From US $538
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
The White House on Oak - Minutes from Louisville From US $236
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Security/Safety
Welcome to Cheerful House From US $284
         

8.6 (13 Reviews)
House
  • TV
  • Balcony/Terrace
  • Security/Safety

About Chickasaw Vacation Rentals

With more than 136 Chickasaw vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Chicagosbestvacationrentals 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 Chickasaw.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Chicagosbestvacationrentals Chickasaw, 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 Chickasaw. Places to stay near Chickasaw are 744.43 ft² on average, with prices averaging US $309 a night.

Chicagosbestvacationrentals makes it easy and safe to find and compare vacation rentals in Chickasaw 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 Chickasaw

Type Count
Vacation Homes 87
Holiday Apartments 32
Hotels 6
B&B 2

Use these Quick Filters to Find a Vacation Rental in Chickasaw

Pro Tip: Chicagosbestvacationrentals makes it easy to compare the best listings on Chicagosbestvacationrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Chicagosbestvacationrentals 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 Chickasaw.

Weather in Chickasaw

View the weather forecast for Chickasaw before booking your Chickasaw 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

Other Places to Stay Near Chickasaw, KY


Chickasaw Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Chickasaw?
How many vacation rentals are available in Chickasaw?

Currently, the total number of properties listed in 2026 is over 136 in the Chickasaw area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chickasaw.