Winfield Vacations from $269

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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.
The Churchill Hotel near Embassy Row
The Waypoint
The Westin Annapolis
Hotel Madera
Eurostars Saint Gregory Dupont Circle Georgetown
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Winfield Hotel Deals

DoubleTree by Hilton Baltimore North - Pikesville

DoubleTree by Hilton Baltimore North - Pikesville

4 out of 5
1726 Reisterstown Rd Pikesville MD
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $127 total per night from Aug 2 to Aug 3
$127 total
Aug 2 - Aug 3
Total with taxes and fees
8/10 Very Good! (1,018 reviews)
"Staff wasn’t helpful at all. We asked for a loading cart and had to wait for 30 minutes and still didn’t get it. The room had bugs and we had to go to Target across the street for bug spray and the sheets were stain with black crust or something. And they also had a wedding there that made it very ..."

Reviewed on Jul 8, 2026

DoubleTree by Hilton Baltimore North - Pikesville
Hyatt Place Baltimore/Owings Mills

Hyatt Place Baltimore/Owings Mills

3 out of 5
4730 Painters Mill Rd Owings Mills MD
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $113 total per night from Jul 26 to Jul 27
$113 total
Jul 26 - Jul 27
Total with taxes and fees
8.2/10 Very Good! (1,345 reviews)
"Great stay"

Reviewed on Jul 13, 2026

Hyatt Place Baltimore/Owings Mills
SpringHill Suites by Marriott Frederick

SpringHill Suites by Marriott Frederick

2.5 out of 5
111 Byte Drive Frederick MD
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $129 total per night from Jul 27 to Jul 28
$129 total
Jul 27 - Jul 28
Total with taxes and fees
9.4/10 Exceptional! (864 reviews)
"The o really stay was excellent."

Reviewed on Jul 13, 2026

SpringHill Suites by Marriott Frederick
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 $269 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.