Gaylord Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Gaylord Vacation
When you choose a Gaylord vacation 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 vacation is a few clicks away with Expedia.
Ready to book your vacation to Gaylord?
Gaylord Hotel Deals
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
Fully refundableReserve now, pay when you stay
CA $123
CA $137 total
Nov 8 - Nov 9
includes taxes & fees
9.2/10 Wonderful! (1,436 reviews)
"Very clean room. Well-lit parking lot."
Reviewed on Oct 8, 2026
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
CA $185
CA $210 total
Oct 29 - Oct 30
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"The staff was just not welcoming or helpful."
Reviewed on Oct 7, 2026
Quality Inn Harpers Ferry - Charles Town
25 Union St Harpers Ferry WV
Fully refundable
CA $127
CA $142 total
Oct 26 - Oct 27
includes taxes & fees
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 vacation package cost?
You can grab a vacation package to this popular destination on Expedia. However, how much your vacation to Gaylord costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Gaylord?
If you're hoping to book a cheap Gaylord vacation package, consider visiting in January, February and March. You'll usually find better prices on airfares and hotels during these months — ideal for a budget-friendly break.
How many days is enough for Gaylord?
With a well-planned itinerary, you can easily hit the top Gaylord sights in a few days. But if you prefer to discover hidden spots or go on day tours, consider booking your Gaylord vacation for longer.
How to find the best Gaylord package deals?
Landing a cheap Gaylord package deal is a breeze with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and see what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Gaylord package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Gaylord vacation as a package?
You can enjoy significant savings on your next Gaylord retreat by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to browse some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Gaylord?
Score incredible discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Gaylord break.
How to plan a trip to Gaylord?
- Pick your dates: What you'd like to do in Gaylord and your favourite season will help you decide when to travel.
- Calculate your budget: Make sure you have enough money to pay for everything from dining out and transportation to activities and airfares. Your accommodations will likely be the biggest expense during your trip to Gaylord.
- Determine how many days away: Start by listing all the attractions you'd like to get to in Gaylord. Then, estimate how long you'll need for each, as well as any travel time.
- Bundle your accommodations and airfare: Once you've settled on your trip dates and duration, book the perfect Gaylord vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
