Gaylord Holidays

    Plan, book, travel with confidence
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    Better together
    Save up to S$120 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

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$102 per night from 1 Jul to 2 Jul
S$102
per night
1 Jul - 2 Jul
7.8/10 Good! (1,066 reviews)
Excellent stay
"Well maintain and friendly operate"

Reviewed on 30 May,2024

Travelodge by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is S$171 per night from 9 Jun to 10 Jun
S$171
per night
9 Jun - 10 Jun
8.8/10 Excellent! (1,357 reviews)
"Excellent stay"

Reviewed on 29 May,2024

La Quinta Inn & Suites 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 S$135 per night from 16 Jun to 17 Jun
S$135
per night
16 Jun - 17 Jun
8.8/10 Excellent! (788 reviews)
"you can always trust the integrity or this property and facility and the staff!"

Reviewed on 31 May,2024

Microtel Inn & Suites by Wyndham Winchester
See all 564 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?
From as little as . Yes, you read that right. Our Gaylord holiday packages are the easiest way to make your budget stretch further. Bundle your preferred hotels, flights and rental car and get out and explore this destination your way.
How do I get a cheap travel package to Gaylord?
Our Gaylord holiday packages mean plenty of savings for the savvy traveller. For the best deals, simply combine your hotel, flights and extras (including activities) into a budget-friendly package. But great bargains are only the start of your next unforgettable adventure. Book with Expedia and and you’ll have over 550 airlines and 1,000,000 hotel options around the globe to choose from. Whatever your budget or style, there’s a holiday package that’s perfect for you.
How far in advance should I book my Gaylord holiday?
Browse Expedia to compare airfares as soon as you know your travel dates. You can usually purchase a seat up to 12 months in advance. If it’s too early for your preferred air carrier, or you’ve left things to the last minute, fear not. The lowest prices to Gaylord occasionally appear a few weeks before the date of departure.
What does an Expedia Gaylord travel package include?
Packages include hotels, flights and rental cars, but you can mix and match them to create your ideal Gaylord holiday. You can also add on fun things like activities and experiences once you’ve made your booking. You’re in charge! When you combine your bookings with Expedia, you’ll get access to deals you won’t find anywhere else.
What should I know before booking a Gaylord travel package?
A travel package can be customized for your budget and is a simple way to make your hard-earned dollars stretch further. How little or much you include is completely up to you. Hotels, rental cars and flights — come up with a combination that suits your plans.
Can I choose my airline with a Gaylord Expedia holiday package?
Yes — and it’s easy too. Expedia has access to more than 550 partner airlines worldwide. Our holiday packages give you the freedom to take your pick of available flights, hotels and activities that fit your needs.
If I'm not able to travel, can I cancel my Gaylord holiday package?
Don’t stress if you’re rethinking your Gaylord holiday package — it’s possible to change or amend your booking. And if you’ve booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We realise life can throw the occasional spanner in the works, so look up our Customer Service Portal if that happens. When you’re ready to make changes, we’ll be here to help.

Popular places to visit

Image for Watermelon Park Campground

Watermelon Park Campground

You can take time to visit Watermelon Park Campground during your travels to Berryville. While in this trendy area, you can savour the wineries and cafes.

Watermelon Park Campground
Image for Mackintosh Fruit Farm

Mackintosh Fruit Farm

Commune with nature and explore the great outdoors at Mackintosh Fruit Farm during your travels in Berryville. While in this family-friendly area, you can savour the top-notch restaurants.

Mackintosh Fruit Farm
Image for The Fire House Gallery

The Fire House Gallery

You can spend time studying the exhibits at The Fire House Gallery during your travels in Berryville. While you're here, you can savour the top-notch restaurants.

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