Gaylord Holidays
Book a Hotel + Flight or Car together to unlock savings
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
Salamander Resort And Spa
500 North Pendleton Street Middleburg VA
Fully refundableReserve now, pay when you stay
£620
14 Sept - 15 Sept
includes taxes & fees
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
£65
28 Sept - 29 Sept
includes taxes & fees
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
£102
7 Sept - 8 Sept
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"Really love this hotel. A bit more luxury with reasonable rates. The rooms are clean, comfortable and well maintained. Onsite bar and restaurant but also many other restaurants, cafes and pubs within walking distance. Ritual Spa onsite is awesome. You have to pay daily for parking but worth the convenience ..."
Reviewed on 31 Aug 2026
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 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.