Gaylord Holidays

  • Plan, book, travel with confidence

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Gaylord

La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is S$145 per night from 6 Jul to 7 Jul
S$145
6 Jul - 7 Jul
includes taxes & fees
9/10 Wonderful! (2,046 reviews)
"Needed a place to sleep for the night with two kids. Room was spacious, clean, comfy. Kids enjoyed the pool (even though it’s not heated) I was able to blast the AC - and use the black out shades. That’s my favorite part of hotels! La Quinta doesn’t disappoint"

Reviewed on 12 Jun, 2025

La Quinta Inn & Suites by Wyndham Winchester
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 S$96 per night from 14 Jul to 15 Jul
S$96
14 Jul - 15 Jul
includes taxes & fees
8.2/10 Very Good! (1,105 reviews)
"Nice"

Reviewed on 9 Jun, 2025

Travelodge by Wyndham Winchester
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 S$134 per night from 15 Jun to 16 Jun
S$134
15 Jun - 16 Jun
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"Excellent stay"

Reviewed on 11 Jun, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 611 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 holiday package cost?
Offering excellent value package deals on Expedia, you’ll be thrilled with how little a holiday to Gaylord costs! Expedia’s packages simplify travel planning and maximise 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 holiday packages and you could get some great off-season deals.
How many days is enough for Gaylord?
With a well-organised 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 holiday 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 holiday package as soon as possible.
Is it cheaper to book a Gaylord holiday as a package?
An Expedia holiday 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 holiday 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 favourite 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 personalised Gaylord holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.