Waddy Vacations from $612

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The Latest Waddy vacation packages

Price found within the past 48 hours. Click for updated prices.
Best Western Premier Airport/Expo Center Hotel

Best Western Premier Airport/Expo Center Hotel

3.5 out of 5
Shively
Price was $785, price is now $612 per person
$612
per person
May 7 - May 10
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
8.6/10 Excellent! (959 reviews)
The room was clean and staff were very friendly and helpful, but i do wish the restaurant and bar were open in the evenings.

Reviewed on Jan 5, 2026

Derby City Gaming & Hotel - A Churchill Downs Property

Derby City Gaming & Hotel - A Churchill Downs Property

4 out of 5
Save 100% on your flight
Price was $3,990, price is now $2,888 per person
$2,888
per person
Apr 29 - May 4
found 18 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
9.4/10 Exceptional! (1,606 reviews)
They were very accommodating. I had failed to book my room correctly and they were more than understanding and helpful with making sure we got everything squared away.

Reviewed on Feb 16, 2026

Staybridge Suites - Louisville - East by IHG

Staybridge Suites - Louisville - East by IHG

3 out of 5
Middletown
Save 100% on your flight
Price was $1,538, price is now $1,171 per person
$1,171
per person
Apr 29 - May 4
found 18 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
8.2/10 Very Good! (658 reviews)
Denise, the manager was great!

Reviewed on Feb 7, 2026

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was $1,156, price is now $905 per person
$905
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
8.8/10 Excellent! (1,002 reviews)
Great hotel in great location. Clean, modern, and artsy. Room was very comfortable and the shower was great, which is big for me. It had good water pressure with hot water. Check in and out was quick and easy.

Reviewed on Jan 20, 2026

Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Price was $817, price is now $644 per person
$644
per person
May 7 - May 10
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
8.8/10 Excellent! (1,005 reviews)
Very clean room, the staff was friendly as well. Looking forward to our stay again next year.

Reviewed on Feb 7, 2026

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Waddy Hotel Deals

Private 7 Acre Estate 6-Bdrm Home+Putting Green+Theatre+Hot Tub+Game Rm+Fire Pit

Private 7 Acre Estate 6-Bdrm Home+Putting Green+Theatre+Hot Tub+Game Rm+Fire Pit

Frankfort KY
$627 nightly
The price is $711 total per night from Feb 17 to Feb 18
$711 total
Feb 17 - Feb 18
Total with taxes and fees
10/10 Exceptional! (3 reviews)
Wonderful location and fantastic space for our family!

Reviewed on Jan 21, 2026

Private 7 Acre Estate 6-Bdrm Home+Putting Green+Theatre+Hot Tub+Game Rm+Fire Pit
✨Luxe Farmhouse✨Bourbon Trail✨ 4 king Beds ✨Hot Tub Games Trails sleeps 16

✨Luxe Farmhouse✨Bourbon Trail✨ 4 king Beds ✨Hot Tub Games Trails sleeps 16

Waddy KY
9.8/10 Exceptional! (32 reviews)
Great hosts!

Reviewed on Jan 31, 2026

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✨Luxe Farmhouse✨Bourbon Trail✨ 4 king Beds ✨Hot Tub Games Trails sleeps 16
Private A-frame Cabin - Hot tub, Firepit & Views

Private A-frame Cabin - Hot tub, Firepit & Views

Waddy KY
10/10 Exceptional! (1 review)
Loved our stay, very clean in a peaceful country setting. Communication with owner was great and very accommodating!!

Reviewed on Nov 9, 2025

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Private A-frame Cabin - Hot tub, Firepit & Views
See all 518 properties in Waddy
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 Waddy Vacation Packages

Waddy Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Blue Grass Airport (LEX)

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Frequently asked questions

How much does a Waddy vacation package cost?
You'll find cheap prices from $612 on Expedia for your Waddy escape. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Waddy costs.
What are the cheapest months to go to Waddy?
November, December and January are the best times to search for cheap Waddy vacation packages. Traveling in less busy periods means you'll typically find reduced prices on flights and hotels.
How many days is enough for Waddy?
The ideal length of your Waddy vacation depends on what you'd like to see and do. Generally, a few days to a week will give you time to tick off all the leading sights and discover some hidden spots along the way.
How to find the best Waddy package deals?
Use Expedia's filters to find some fabulous Waddy package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Waddy package deals in the off-season. Switch up 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 a Waddy vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging accommodations and flights individually. Better still, you can tailor your Waddy getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Waddy?
If you're considering a spur-of-the-moment Waddy adventure, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find amazing deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Waddy vacation packages?
Your Waddy getaway is meant to be a relaxing escape from your busy life, not a reason for money worries. So to give you extra flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.