Gaylord Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 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

Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street Middleburg VA
The price is ￥97,479 per night from Aug 19 to Aug 20
￥97,479
￥120,277 total
Aug 19 - Aug 20
includes taxes & fees
9.2/10 Wonderful! (410 reviews)
"The property and staff are amazing. Lots to do if you bring the kiddos, the kids camp let's adults relax and enjoy amenities. The one thing the property can work on is the food menu; more variety is needed. The Red Horse Tavern is a 5-minute walk into town and has the best food!!"

Reviewed on Jul 21, 2026

Salamander Resort And Spa
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike Winchester VA
Fully refundable
The price is ￥13,608 per night from Aug 16 to Aug 17
￥13,608
￥15,637 total
Aug 16 - Aug 17
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
"Check in was quick and easy. Clerk was wonderful and knowledgeable about the area. Over all a pleasant stay."

Reviewed on Jul 27, 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
The price is ￥17,330 per night from Aug 10 to Aug 11
￥17,330
￥19,289 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (1,025 reviews)
"Très bien!"

Reviewed on Jul 27, 2026

TRU By Hilton Winchester
See all 690 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?
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 can usually find lower rates and better availability in January, February and March. Check out our cheap Gaylord vacation packages and you could get some great off-season deals.
How many days is enough for Gaylord?
With a well-organized schedule, you can easily tick off the main Gaylord attractions in a handful of days. But if you'd like to discover lesser-known spots or go on day tours, consider booking your Gaylord vacation for longer.
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.
How to plan a trip to Gaylord?

  1. Choose when to go: Check your calendar and get your bags packed. Your favorite time of year and the activities available will also help you decide when to escape to Gaylord.
  2. Plan your budget wisely: Besides the price of your hotel, you should factor in other expenses. These include food, flights and transportation. Also, set aside a little extra for unexpected costs that may crop up during your trip to Gaylord.
  3. Determine how many days away: Start by compiling a list of the attractions you want to experience in Gaylord. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalized Gaylord vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.