Rolling Fields Vacation Packages

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Your Rolling Fields Vacation

Say bye-bye to the worries of planning and hello to a Rolling Fields vacation package. With everything organized before you take off, you can focus on discovering the best of this city, starting with East Market District, which is good for nightlife, distilleries and craft breweries and shopping. If your trip to Rolling Fields includes a little sightseeing, drop by renowned attractions like E.P. Tom Sawyer State Park, Mall St. Matthews and Paddock Shops. Check out Expedia's extensive range of travel options and start organizing your perfect vacation to Rolling Fields now.

Top Holiday Package Deals in Rolling Fields

Price found within the past 48 hours. Click for updated prices.
Derby City Gaming & Hotel - A Churchill Downs Property

Derby City Gaming & Hotel - A Churchill Downs Property

4 out of 5
per person
Sep 7 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
9.4/10 Exceptional! (1,265 reviews)
The housekeepers need a raise. This is the CLEANEST place we’ve stayed in all the states we’ve visited. Comfortable, clean, safe.

Reviewed on Jul. 15, 2025

The Brown Hotel

The Brown Hotel

4.5 out of 5
Downtown Louisville
per person
Sep 18 - Sep 22
found 14 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Louisville (SDF)
9.4/10 Exceptional! (1,018 reviews)
The sense of history enhanced the stay, and the classic hotel appointments were appreciated.

Reviewed on Jul. 15, 2025

Hancock House

Hancock House

3 out of 5
Downtown Louisville
per person
Sep 18 - Sep 22
found 14 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Louisville (SDF)
8/10 Very Good! (237 reviews)
Excellent location, great parking, well equipped apartment with a comfortable bed. I’d highly recommend to anyone wanting to explore Louisville, and will definitely stay again!

Reviewed on Jul. 3, 2025

21c Museum Hotel Louisville

21c Museum Hotel Louisville

4.5 out of 5
Downtown Louisville
per person
Sep 7 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
9.2/10 Wonderful! (1,000 reviews)
Great Location. Great hotel. Great team members.

Reviewed on Jul. 14, 2025

Pillow and Paddock B&B

Pillow and Paddock B&B

3.5 out of 5
per person
Sep 18 - Sep 22
found 14 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Louisville (SDF)
10/10 Exceptional! (48 reviews)
This has been our second time staying here and we will continue to come back. Beautiful home, amazing breakfasts, and wonderful hosts, not much else we could ask for.

Reviewed on Apr. 27, 2025

Where to stay in Rolling Fields

Find the best Rolling Fields areas and neighborhoods for the activities you enjoy most. Learn more about Rolling Fields
Louisville showing signage and street scenes as well as a small group of people

Downtown Louisville

4 out of top 10 points of interest in this area
4/5(37 area reviews)

Explore "Museum Row" in the West Main District, catch a game at Louisville Slugger Field, or stroll across the pedestrian-only Big Four Bridge. Enjoy diverse attractions, restaurants, and the Louie Link skywalk.

Find hotels in Downtown Louisville

Rolling Fields Hotel Deals

Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

4 out of 5
140 North Fourth Street, Louisville, KY
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from Aug 16 to Aug 17
CA $191
CA $225 total
Aug 16 - Aug 17
includes taxes & fees
8.8/10 Excellent! (3,445 reviews)
"Downtown location. Beautiful room!"

Reviewed on Jul. 12, 2025

Galt House Hotel Trademark Collection by Wyndham
Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
830 Phillips Lane, Louisville, KY
Fully refundableReserve now, pay when you stay
The price is CA $129 per night from Jul 21 to Jul 22
CA $129
CA $152 total
Jul 21 - Jul 22
includes taxes & fees
8.6/10 Excellent! (654 reviews)
"Would recommend"

Reviewed on Jul. 14, 2025

Crowne Plaza Louisville Airport Expo Ctr by IHG
Omni Louisville Hotel

Omni Louisville Hotel

4 out of 5
400 S. 2nd Street, Louisville, KY
Fully refundableReserve now, pay when you stay
The price is CA $218 per night from Aug 8 to Aug 9
CA $218
CA $257 total
Aug 8 - Aug 9
includes taxes & fees
9/10 Wonderful! (1,508 reviews)
"The staff at the hotel were wonderful, very welcoming and friendly. The room was a bit dated and there was a large stain on the side of one of the beds mattress covers. I slept in the other bed so I did not bring it to anyone's attention. The banquet food was not the best, and the carpet in the meeting ..."

Reviewed on Jul. 15, 2025

Omni Louisville Hotel
See all 2,006 properties in Rolling Fields
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

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Family Vacations

Frequently asked questions

How much does a Rolling Fields vacation package cost?
Starting from as low as CA $1,007, a package is your ticket to inexpensive travel. Custom make your Rolling Fields trip by selecting from our great range of flights, hotels and rental cars.
How do I get a cheap travel package to Rolling Fields?
Search for flights that fit your schedule, add a hotel room to your booking and watch the savings rack up with a Rolling Fields vacation package. It's that easy! From hotels and flights to rental cars and tours, Expedia is where your cheap getaway begins. And with over 550 partner airlines and 1,000,000 hotel options globally to select from, you won't be short of choice.
Where should I stay in Rolling Fields?
With popular attractions like Mall St. Matthews and Baptist Hospital Louisville in this neighborhood, see if you can find a hotel near either of them. Historic Frankfort Avenue is another Rolling Fields hot spot that lures the crowds.
How far in advance should I book my Rolling Fields vacation?
It's hard to pick the perfect time for airfares, but we usually say the earlier, the better. Most international flights on Expedia become available up to a year in advance. If you're booking late, fear not. Bargain prices occasionally appear within a few weeks of departure dates.
What does an Expedia Rolling Fields travel package include?
It all boils down to what kind of escape you're contemplating. Rolling Fields travel deals can include car rentals, flights and hotels. You can mix and match to find the bundle that fits your needs. You can also add on experiences and activities after you've booked to pick up even bigger discounts.
What should I know before booking a Rolling Fields travel package?
A travel package can be customized for your circumstances and is a simple way to stretch your hard-earned dollars. How little or much you include is your call. Hotels, rental cars and flights --- choose any combination that suits your style.
Can I choose my airline with a Rolling Fields Expedia vacation package?
Yes --- and it's easy too. Expedia has access to more than 550 partner airlines worldwide. Our packages give you the flexibility to take your pick of available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Rolling Fields vacation package?
Yes, you can cancel your Rolling Fields booking if your plans have been upended. Whether you'll incur a penalty or not depends on your hotel, airline or car rental company. It may be possible to cancel or change your booking free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.

Discover the most popular places to visit in Rolling Fields

Kentucky Exposition Center

Kentucky Exposition Center

4.5/5(14 reviews)

Learn about the events happening at Kentucky Exposition Center during your trip to Louisville. Experience the area's lively festivals and great live music.

Kentucky Exposition Center
Churchill Downs showing land animals and horse riding as well as a small group of people

Churchill Downs

4.5/5(22 reviews)

Find more than mint juleps to enjoy at this iconic racetrack, best known as the annual host of the Kentucky Derby.

Churchill Downs
Louisville Slugger Museum featuring interior views

Louisville Slugger Museum

4.5/5(18 reviews)

Baseball is part of the American fabric. See where one important tool for this sport is produced in the factory that makes ball games possible.

Louisville Slugger Museum

Things to do

Derby City Ghosts: Louisville Hauntings Tour

Derby City Ghosts: Louisville Hauntings Tour

CA $36
per adult
Derby City Ghosts: Louisville Hauntings Tour
Where every day is Derby Day!

Kentucky Derby Museum General Admission Ticket

CA $30
per adult
90% of travellers recommend
Kentucky Derby Museum General Admission Ticket
Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

CA $41
per traveller
Self Guided Driving Tour to Four Kentucky Bourbon Distilleries
See all activities in Louisville
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.