Gaylord Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 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

    Packages with flights are ATOL protected

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

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 £58 per night from 1 Dec to 2 Dec
£58
1 Dec - 2 Dec
includes taxes & fees
Travelodge 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 £68 per night from 3 Nov to 4 Nov
£68
3 Nov - 4 Nov
includes taxes & fees
9.2/10 Wonderful! (1,432 reviews)
"Better pillows Also there was tv guide in room"

Reviewed on 31 Oct 2026

Microtel Inn & Suites by Wyndham Winchester
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
The price is £110 per night from 8 Nov to 9 Nov
£110
8 Nov - 9 Nov
includes taxes & fees
The George Washington Hotel, A Wyndham Grand Hotel
See all 689 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

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.