Winfield Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Winfield Vacation Packages

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
The price is SARĀ 413 per night from Aug 5 to Aug 6
SARĀ 413
SARĀ 477 total
5 Aug - 6 Aug
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"Decent enough hotel for the price; ample parking, under construction in the lobby area but staff was dedicated and helpful."

Reviewed on 17 July 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
The price is SARĀ 368 per night from Jul 26 to Jul 27
SARĀ 368
SARĀ 425 total
26 Jul - 27 Jul
includes taxes & fees
8.2/10 Very Good! (1,341 reviews)
"Breakfast wasnā€™t good at all."

Reviewed on 17 July 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
The price is SARĀ 470 per night from Aug 13 to Aug 14
SARĀ 470
SARĀ 521 total
13 Aug - 14 Aug
includes taxes & fees
SpringHill Suites by Marriott Frederick
See all 219 properties in Winfield
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 Winfield vacation package cost?
You can grab a vacation package to this destination on Expedia. But how much your vacation to Winfield costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Winfield?
January, February and November are great times to search for cheap Winfield vacation packages. Choosing to travel in quieter months means you can typically find better prices on flights and hotels.
How to find the best Winfield package deals?
Use Expedia's filters to find some of the best Winfield package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Winfield package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Winfield vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging hotels and flights individually. Better still, you can tailor your Winfield getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Winfield?
If you're considering an impromptu Winfield getaway, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Winfield?

  1. Pick the ideal time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to visit Winfield.
  2. Set a budget: Consider expenses such as flights, food and transportation when working out how much to save for your trip to Winfield. Then, choose a property that fits your budget, whether that's an affordable option or a high-end getaway.
  3. Work out your trip length: Think about how long you want to spend exploring Winfield. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to find a Winfield vacation package that brings all your bookings together.