Winfield Vacations from $298
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Your Winfield Vacation
Take away the hard part of organizing your next big adventure with a Winfield vacation package. Whether you're in town for its history, food or other highlights, you'll find countless exciting experiences to delve into. There's plenty to put on your itinerary during your trip to Winfield, starting with top attractions such as Old Westminster Winery and Serpent Ridge Vineyard. No matter your travel plans or the size of your budget, organizing a tailored Winfield vacation is a breeze with Expedia.
The Latest Winfield vacation packages
Price found within the past 48 hours. Click for updated prices.
Winfield Hotel Deals
DoubleTree by Hilton Baltimore North - Pikesville
1726 Reisterstown Rd Pikesville MD
Fully refundableReserve now, pay when you stay
$130 nightly
$151 total
Oct 30 - Oct 31
Total with taxes and fees
8/10 Very Good! (1,007 reviews)
"Great service. Enjoyed my stay."
Reviewed on Oct 12, 2026
Hyatt Place Baltimore/Owings Mills
4730 Painters Mill Rd Owings Mills MD
Fully refundableReserve now, pay when you stay
$98 nightly
$113 total
Oct 20 - Oct 21
Total with taxes and fees
8.2/10 Very Good! (1,402 reviews)
"Stay away if you can. Very dirty. Sofa cover was super dirty and never been cleaned. We can’t even seat. You can see the dirty cover then the bedsheets are dirty. First they give us room 511 once I opened the sofa bed I see used water bottle and lotion bottle etc. they don’t even change the bed cover. ..."
Reviewed on Oct 12, 2026
Marriott Owings Mills Metro Centre
10101 Grand Central Avenue Owings Mills MD
Fully refundableReserve now, pay when you stay
$166 nightly
$192 total
Oct 18 - Oct 19
Total with taxes and 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.
Find the Best Winfield Vacation Packages
Winfield Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Baltimore Washington Intl. Thurgood Marshall Airport (BWI) |
Top Sights | Serpent Ridge Vineyard, McDaniel College and Carroll County Farm Museum |
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Frequently asked questions
How much does a Winfield vacation package cost?
Offering excellent value package deals from $298 on Expedia, you'll be thrilled with how little a vacation to Winfield costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Winfield?
November, December and January are great times to look for cheap Winfield vacation packages. Traveling in less busy periods means you'll typically find better prices on flights and accommodations.
How many days is enough for Winfield?
Generally, a handful of days is enough to go to the top sights during your Winfield vacation. But if you want to have time to kick back or take day trips, consider extending your trip.
How to find the best Winfield package deals?
Use Expedia's filter tool to find some terrific Winfield package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Winfield package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Winfield vacation as a package?
You can enjoy significant savings on your next Winfield escape by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to see the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Winfield?
If you're considering a spur-of-the-moment Winfield trip, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land awesome deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Winfield vacation packages?
Set off on your ideal getaway to Winfield with Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait for payday — we've joined forces with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily budget for your trip and snag great deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
