Gaylord Holidays

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Your Gaylord Holiday

When you choose a Gaylord holiday package, it's all about enjoying your escape to the fullest. Delve into the best things about this fascinating city knowing that all the travel planning has been worked out in advance. Mackintosh Fruit Farm, Veramar Vineyard and Barns of Rose Hill are just some of the sights worth visiting during your trip to Gaylord. Don't put off visiting this city any longer. Your dream Gaylord holiday is a few clicks away with Expedia.

Gaylord Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Washington Dulles Intl. Airport (IAD)
Max Temp Winter
4ºC
Max Temp Summer
29ºC
Top Sights
Veramar Vineyard, 612 Vineyard and The Fire House Gallery

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 £83 per night from 1 Sept to 2 Sept
£83
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (2,133 reviews)
"Just a suggestion. I am disabled and was placed in a lovely room on the 6th floor. The fire alarm went off and my concern is how is someone in a wheelchair going to evacuate without the elevator. Maybe all ada rooms shou"

Reviewed on 19 Aug 2025

La Quinta Inn & Suites by Wyndham Winchester
Quality Inn

Quality Inn

2.5 out of 5
25 Union St, Harpers Ferry, WV
Fully refundableReserve now, pay when you stay
The price is £67 per night from 1 Sept to 2 Sept
£67
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
"We found the motel comfortable and convenient."

Reviewed on 13 Aug 2025

Quality Inn
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 £68 per night from 31 Aug to 1 Sept
£68
31 Aug - 1 Sept
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"Bed comfort"

Reviewed on 12 Aug 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 618 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

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

Barns of Rose Hill

After visiting Barns of Rose Hill, make a plan to see the other sights and activities in Berryville. While you're here, you can savour the top-notch restaurants.

Barns of Rose Hill

Frequently asked questions

How much does a Gaylord travel package cost?
The most affordable Gaylord package is , so your dream escape can become a reality — without a hefty price tag. Combine flights, hotels and car rentals to build a package suited to your travel style.
If I'm not able to travel, can I cancel my Gaylord travel package?
Whether it's your hotel, flight or rental car, yes, you can cancel or amend it. Booked your Gaylord travel package in the last 24 hours? You may be able to make changes at no cost. For bookings made more than 24 hours ago, you may incur a charge from your hotel, airline or car rental company. For more details, head to our Customer Service Portal. We'll help you every step of the way.
How do I get a cheap travel package to Gaylord?
Our Gaylord travel packages promise plenty of savings for the savvy wanderer. For the best deals, simply bundle your hotel, flights and rental cars into an affordable package. But low prices are just the beginning of your next memorable adventure. When you book with Expedia, you'll have more than 550 air carriers and 1,000,000 hotels all over the world to select from. Whatever your budget or style, there's a package with your name on it.
Does Expedia offer Book Now, Pay Later Gaylord holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has devised a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book an incredible getaway without making a dent in your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your escape. Consider one of these flexible payment options:

  • Pay monthly holidays: Klarna has manageable monthly payment plans that fit all budgets, so you can escape on that well-deserved holiday now.
  • Pay in instalments holidays: Into the idea of paying off your holiday in multiple transactions? Then select this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: Clicking on the "book now" button is easier with this payment option. Simply put down a small deposit on your escape and then start packing your bags.

What are the top hotels in Gaylord?
Lock in a room at Smithfield Farm B&B. It's one of the area's most popular properties. Another well-known option in Gaylord is The Outpost Suite 3 - Whimsical Farmhouse Retreat.
How far in advance should I book my Gaylord holiday?
Reserving your tickets early with Expedia means one less thing to have to worry about. A number of air carriers advertise prices up to 12 months in advance. Usually, this is the cheapest time to book. If circumstances have left you booking late, last-minute deals to Gaylord sometimes become available in the weeks leading up to departure.
What does an Expedia Gaylord travel package include?
Hotels, car rentals and flights — we bring you the very best bargains. All you have to do is select your preferred combination. Once you've made your booking, you can add on the exciting stuff like tours and experiences. Our travel packages make it simple to put together an awesome Gaylord holiday.
What should I know before booking a Gaylord travel package?
Whether it's adventure or relaxation you're craving, a Gaylord travel package lets you plan your escape your way. Plus, you'll get access to great discounts when you combine your accommodation with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with a Gaylord Expedia travel package?
Yes — that's the beauty of an Expedia travel package. You get to decide. We have access to more than 550 partner airlines globally, so you have lots of choice when arranging your Gaylord escape.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.