Gaylord Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AEDĀ 5,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Gaylord Vacation Packages

Gaylord Hotel Deals

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
The price is AEDĀ 257 per night from Dec 1 to Dec 2
AEDĀ 257
AEDĀ 284 total
1 Dec - 2 Dec
includes taxes & fees
Travelodge by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza Winchester VA
Fully refundableReserve now, pay when you stay
The price is AEDĀ 291 per night from Nov 15 to Nov 16
AEDĀ 291
AEDĀ 324 total
15 Nov - 16 Nov
includes taxes & fees
Microtel Inn & Suites by Wyndham Winchester
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
The price is AEDĀ 479 per night from Nov 19 to Nov 20
AEDĀ 479
AEDĀ 543 total
19 Nov - 20 Nov
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"Nice and comfortable for a get away weekend."

Reviewed on 11 November 2026

The George Washington Hotel, A Wyndham Grand Hotel
See all 680 properties in Gaylord
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.

Frequently asked questions

How much does a Gaylord vacation package cost?
You can grab a vacation package to this popular destination on Expedia. However, how much your vacation to Gaylord costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Gaylord?
If you're hoping to book a cheap Gaylord vacation package, consider visiting in January, February and March. You'll usually find better prices on airfares and hotels during these months ā€” ideal for a budget-friendly break.
How to find the best Gaylord package deals?
Landing a cheap Gaylord package deal is a breeze with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and see what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Gaylord package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Gaylord vacation as a package?
You can enjoy significant savings on your next Gaylord retreat by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to browse some great flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Gaylord?
Score incredible discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Gaylord break.
How to plan a trip to Gaylord?

  1. Pick your dates: What you'd like to do in Gaylord and your favorite season will help you decide when to travel.
  2. Calculate your budget: Make sure you have enough money to pay for everything from dining out and transportation to activities and airfares. Your accommodations will likely be the biggest expense during your trip to Gaylord.
  3. Determine how many days away: Start by listing all the attractions you'd like to get to in Gaylord. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your accommodations and airfare: Once you've settled on your trip dates and duration, book the perfect Gaylord vacation package for you.