Waddy Vacations from $332
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The Latest Waddy vacation packages
Price found within the past 48 hours. Click for updated prices.
Regina's Country Livin'
$332
per person
Dec 11 - Dec 14
found 10 hours ago
Roundtrip flight included
Miami (MIA) to Louisville (SDF)
9.6/10 Exceptional! (14 reviews)
If I am ever doing something between Louisville and Lexington, I will be visiting Regina. This house was well-designed as a true BNB with excellent access/security, thoughtful decor, and an extremely welcoming atmosphere. The reviews praising the breakfast are true - but don't just go for the biscuits and gravy, go for the full experience.
Reviewed on Sep 28, 2026
Pillow and Paddock B&B
$721
per person
Dec 11 - Dec 14
found 7 hours ago
Roundtrip flight included
Miami (MIA) to Louisville (SDF)
10/10 Exceptional! (52 reviews)
Courteous staff and the room was outstanding. It was our second stay at the inn. Everything is first class. We highly recommend it.
Reviewed on Dec 22, 2025
Waddy Hotel Deals
✨Luxe Farmhouse✨Bourbon Trail✨ 4 king Beds ✨Hot Tub Games Trails sleeps 16
Waddy KY
10/10 Exceptional! (50 reviews)
"Extremely clean house. It was perfect for 4 couples doing the bourbon tour. The hot tub and fire pit were used almost every day. The property does back up onto I64 so there is some freeway noise outside. We would stay here again without hesitation."
Reviewed on Oct 16, 2026
The Delegate
106 E. Broadway Street Frankfort KY
$135 nightly
$158 total
Nov 15 - Nov 16
Total with taxes and fees
9.2/10 Wonderful! (571 reviews)
"Very clean, helpful staff, attached restaurant has the best food in town."
Reviewed on Oct 17, 2026
Bluegrass Inn
635 Versailles Road Frankfort KY
Fully refundableReserve now, pay when you stay
$78 nightly
$92 total
Nov 18 - Nov 19
Total with taxes and fees
8/10 Very Good! (1,005 reviews)
"It was clean and comfortable. We only stayed one night but would stay again."
Reviewed on Oct 18, 2026
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 $332 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.
