Dillard Vacations from $1,089
Book a Hotel + Flight or Car together to unlock savings
The Latest Dillard vacation packages
Price found within the past 48 hours. Click for updated prices.
Proximity Hotel
$1,154
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
9.8/10 Exceptional! (1,003 reviews)
Hotel was beautiful, room was immaculate. I loved the double doors that open to the bathroom that connected to the room!!! I will be staying there again! 10/10
Reviewed on Aug 30, 2026
O.Henry Hotel
$1,206
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
9.8/10 Exceptional! (849 reviews)
It's our third time staying, & the staff remains exemplary. They are the standout and the reason that we will always stay at the o henry. It was wonderful seeing Sherone again. Hannah, Lakiya,& other front desk goddesses are delightful. The tea & jazz staff are fantastic. Kate & Courtney improved our mornings dramatically, & Ashleigh was lovely for our dinner.
Tyler and the other porters are fantastic at their jobs, though it hurt my heart to see them dressed like it was 50 degrees out amidst the brutal heat & humidity. It would be lovely if they could lose the sweater vest and long sleeves and have more suitable summer attire.
The only downside was I had to use my cell as a Hotspot to access wifi for my tablet, my dad's laptop, and our Amazon fire.
Reviewed on Aug 31, 2026
Dillard Hotel Deals
DoubleTree by Hilton Winston Salem - University
5790 University Pkwy Winston-Salem NC
Fully refundableReserve now, pay when you stay
$98 nightly
$111 total
Sep 13 - Sep 14
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
"No business center, no restaurant or bar. Not usual DoubleTree standards!"
Reviewed on Aug 31, 2026
Spark by Hilton Winston-Salem University
200 Mercantile Dr Winston-Salem NC
Fully refundableReserve now, pay when you stay
$81 nightly
$92 total
Sep 20 - Sep 21
Total with taxes and fees
8.4/10 Very Good! (325 reviews)
"Everything especially the wonderful staff!!"
Reviewed on Aug 31, 2026
Hampton Inn & Suites Winston-Salem/University Area, NC
309 Summit Square Ct Winston-Salem NC
Fully refundableReserve now, pay when you stay
$98 nightly
$110 total
Sep 10 - Sep 11
Total with taxes and fees
9/10 Wonderful! (1,007 reviews)
"Easy check in and pet friendly"
Reviewed on Sep 1, 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 Dillard Vacation Packages
Dillard Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Piedmont Triad Intl. Airport (GSO) |
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Frequently asked questions
How much does a Dillard vacation package cost?
You'll find cheap prices from $1,089 on Expedia for your Dillard break. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Dillard costs.
What are the cheapest months to go to Dillard?
November, December and January are the best times to search for cheap Dillard vacation packages. Choosing to travel in quieter periods means you can typically find lower prices on hotels and flights.
How many days is enough for Dillard?
The ideal length for your Dillard vacation depends on what you'd like to see. Typically, a handful of days to a week will give you enough time to check out all the top sights and discover some hidden gems along the way.
How to find the best Dillard package deals?
Start your search for a Dillard package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Dillard package deal right away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Dillard adventure off to a flying start.
Is it cheaper to book a Dillard vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component separately. And you'll still get the flexibility to create a tailored Dillard vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Dillard?
Enjoy incredible bargains by booking your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Dillard getaway.
Does Expedia offer Book Now, Pay Later Dillard vacation packages?
Set off on your perfect escape to Dillard with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait until your next paycheck — we've teamed up with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no late payment fees or extra charges, you can easily budget for your trip and snap up travel deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.