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 1 Sept to 2 Sept
S$145
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (2,123 reviews)
"One of our fave places to stay when we visit Winchester."

Reviewed on 10 Aug, 2025

La Quinta Inn & Suites 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 17 Aug to 18 Aug
S$134
17 Aug - 18 Aug
includes taxes & fees
9/10 Wonderful! (1,011 reviews)
"Very nice staff, clean. Restaurant on premises with good bkfst"

Reviewed on 11 Aug, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
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 S$111 per night from 2 Sept to 3 Sept
S$111
2 Sept - 3 Sept
includes taxes & fees
9/10 Wonderful! (1,324 reviews)
Economical, spotless
"Great price , spotlessly clean. Have stayed here several times for one night, will stay again!"

Reviewed on 10 Aug, 2025

Microtel Inn & Suites by Wyndham Winchester
See all 621 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.