Gaylord Vacations
Book a Hotel + Flight or Car together to unlock savings
Your Gaylord Vacation
When you choose a Gaylord vacation package, it's all about enjoying your escape to the fullest. Delve into the best things about this fascinating city knowing that all the travel planning has been worked out in advance. Mackintosh Fruit Farm, Veramar Vineyard and Barns of Rose Hill are just some of the sights worth visiting during your trip to Gaylord. Don't put off visiting this city any longer. Your dream Gaylord vacation is a few clicks away with Expedia.
Gaylord Hotel Deals
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
Fully refundableReserve now, pay when you stay
$86 nightly
$96 total
Nov 8 - Nov 9
Total with taxes and fees
9.2/10 Wonderful! (1,436 reviews)
"Very clean room. Well-lit parking lot."
Reviewed on Oct 8, 2026
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
$130 nightly
$148 total
Oct 28 - Oct 29
Total with taxes and fees
9.4/10 Exceptional! (1,001 reviews)
"The staff was just not welcoming or helpful."
Reviewed on Oct 7, 2026
Quality Inn Harpers Ferry - Charles Town
25 Union St Harpers Ferry WV
Fully refundable
$89 nightly
$100 total
Oct 26 - Oct 27
Total with taxes and fees
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 Gaylord Vacation Packages
Gaylord Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Washington Dulles Intl. Airport (IAD) |
Top Sights | Veramar Vineyard, 612 Vineyard and The Fire House Gallery |
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Frequently asked questions
How much does a Gaylord vacation package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a vacation to Gaylord costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Gaylord?
You're likely to find lower prices and better availability in January, May and July. Take a look at our cheap Gaylord vacation packages and you could land some excellent off-season deals.
How many days is enough for Gaylord?
Typically, a handful of days is enough to explore the top attractions during your Gaylord vacation. But if you'd like to have time to rest or take day trips, consider extending your trip.
How to find the best Gaylord package deals?
Use Expedia's handy filters to find some tempting Gaylord package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Gaylord package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Gaylord vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and hotels individually. Better still, you can tailor your Gaylord getaway to match 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 Gaylord?
Land amazing discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Gaylord break.
Does Expedia offer Book Now, Pay Later Gaylord vacation packages?
If you're like us, you love traveling the world but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Gaylord vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.