Eastwood Vacations from $482

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Your Eastwood Vacation

The exciting city of Eastwood is calling your name. Uncover both its hidden gems and highlights with a Eastwood vacation package that's tailored to you. Fill your spare time with tours of The Outlet Shoppes of the Bluegrass, Southeast Christian Church and Beckley Creek Park, some of the top attractions you shouldn't miss during a trip to Eastwood. Check out Expedia's wide range of travel options and start planning your ideal vacation to Eastwood now.

The Latest Eastwood vacation packages

Price found within the past 48 hours. Click for updated prices.
Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Shively
Price was $583, price is now $482 per person
$482
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
8.8/10 Excellent! (1,012 reviews)
Decent place to stay. Staff helpful and nice.

Reviewed on Nov 2, 2026

Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
Fairgrounds
Price was $686, price is now $553 per person
$553
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
8.8/10 Excellent! (1,902 reviews)
The staff was great. The bar and restaurant top notch. The hotel is wonderful. This was my second stay there and I will stay there again.

Reviewed on Nov 3, 2026

Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

4 out of 5
Downtown Louisville
Price was $1,638, price is now $1,332 per person
$1,332
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9.6/10 Exceptional! (511 reviews)

The Brown Hotel

The Brown Hotel

4.5 out of 5
Downtown Louisville
Price was $681, price is now $563 per person
$563
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
9.4/10 Exceptional! (1,397 reviews)

The Grady

The Grady

4 out of 5
Downtown Louisville
Price was $1,519, price is now $1,265 per person
$1,265
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9.4/10 Exceptional! (1,003 reviews)
It’s a nice hotel but definitely not 5⭐️the bed was not comfortable,the hotel was not busy and the room they gave us was mediocre@best ans being a Hilton platinum member an upgrade would’ve been appreciated,our room was freezing,not exactly the most hospitable staff member that booked us in,otherwise staff was nice,but again not 5 stars.

Reviewed on Nov 2, 2026

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What to do in Eastwood

Kentucky Derby Museum

Kentucky Derby Museum - General Admission and Guided Track Visit

$24
per adult
94% of travellers recommend
Kentucky Derby Museum - General Admission and Guided Track Visit
Old Louisville Ghost Tour as Recommended by The New York Times @ 4th and Ormsby

Old Louisville Ghost Tour as Recommended by The New York Times @ 4th and Ormsby

$29
per adult
92% of travellers recommend
Old Louisville Ghost Tour as Recommended by The New York Times @ 4th and Ormsby
See all activities in Eastwood

Eastwood 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
$134 nightly
The price is $158 total per night from Nov 16 to Nov 17
$158 total
Nov 16 - Nov 17
Total with taxes and fees
9/10 Wonderful! (4,442 reviews)
"Walkable to 4th st live"

Reviewed on Nov 4, 2026

Galt House Hotel Trademark Collection by Wyndham
The Brown Hotel

The Brown Hotel

4.5 out of 5
335 W Broadway Louisville KY
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $153 total per night from Nov 25 to Nov 26
$153 total
Nov 25 - Nov 26
Total with taxes and fees
The Brown Hotel
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

4 out of 5
4520 Poplar Level Rd Louisville KY
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $107 total per night from Nov 8 to Nov 9
$107 total
Nov 8 - Nov 9
Total with taxes and fees
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)
See all 2,084 properties in Eastwood
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.

Find the Best Eastwood Vacation Packages

Eastwood Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Louisville Intl. Airport (SDF)
Top Sights
Kentucky Artisan Distillery, Locust Grove Historic Home and Talon Winery

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Frequently asked questions

How much does an Eastwood vacation package cost?
Offering great value package deals from $482 on Expedia, you'll be thrilled with how little a vacation to Eastwood costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Eastwood?
November, December and January are the best times to search for cheap Eastwood vacation packages. Opting to travel in quieter months means you'll typically find lower prices on hotels and flights.
How many days is enough for Eastwood?
The ideal length for your Eastwood vacation depends on what you'd like to see. Typically, a few days to a week will give you enough time to check out all the major sights and discover some hidden treasures along the way.
How to find the best Eastwood package deals?
Use Expedia's handy filters to help you find some fabulous Eastwood package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Eastwood package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book an Eastwood vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and hotels separately. Better still, you can personalize your Eastwood getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Eastwood?
If you've got your Eastwood travel dates confirmed, book early to bag some terrific deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Eastwood vacation packages?
Your Eastwood trip should be an escape from your busy life, not a source of money-related stress. So to allow you extra flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.