Westfield Vacations from $628

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The Latest Westfield vacation packages

Price found within the past 48 hours. Click for updated prices.
The Shaffner Inn

The Shaffner Inn

2 out of 5
Price was $701, price is now $628 per person
$628
per person
Dec 26 - Dec 29
found 10 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Greensboro (GSO)
9.2/10 Wonderful! (250 reviews)
This is a beautiful old inn that has timeless charm. Very comfortable space, very clean, and wonderful owner and staff. The breakfast was delicious: fresh scrambled eggs, perfectly cooked stone ground grits, fresh bread for toasting and fresh blueberries and strawberries. The artwork shown in the front rooms was an unexpected plus! So cool! Wifi worked well. An elegant and comfortable stay: thank you!

Reviewed on Nov 1, 2026

Pandora's Manor Bed & Breakfast

Pandora's Manor Bed & Breakfast

3.5 out of 5
West High Avenue Historic District
Price was $1,428, price is now $1,232 per person
$1,232
per person
Dec 26 - Dec 29
found 10 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Greensboro (GSO)
10/10 Exceptional! (2 reviews)
Thanks for a wonderful stay. The property is beautiful and well kept. I was able to get some peace and quiet while attending GHOE and checking on the remodeling of one of my rental properties. I got the best rest during my stay. The property is safe and secure. The staff was very attentive and friendly. Definitely a home away from home. Will stay again.

Reviewed on Nov 1, 2026

O.Henry Hotel

O.Henry Hotel

4 out of 5
Price was $1,000, price is now $901 per person
$901
per person
Dec 26 - Dec 29
found 10 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Greensboro (GSO)
9.8/10 Exceptional! (879 reviews)

Proximity Hotel

Proximity Hotel

4 out of 5
Price was $958, price is now $867 per person
$867
per person
Dec 26 - Dec 29
found 10 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Greensboro (GSO)
9.8/10 Exceptional! (1,000 reviews)
Clean room and the restaurant of the hotel is nice. Not a lot of storage space in the room but it did have a nice modern design

Reviewed on Nov 2, 2026

Amos Dr

Amos Dr

2 out of 5
Price was $840, price is now $767 per person
$767
per person
Dec 10 - Dec 13
found 4 hours ago
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
No reviews

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Westfield Hotel Deals

Suburban Studios Winston Salem-University Parkway

Suburban Studios Winston Salem-University Parkway

2 out of 5
7910 N Point Blvd Winston-Salem NC
$55 nightly
The price is $62 total per night from Dec 1 to Dec 2
$62 total
Dec 1 - Dec 2
Total with taxes and fees
6.2/10 (1,002 reviews)
"It's to Ghetto for me. I really wouldn't come there again."

Reviewed on Nov 1, 2026

Suburban Studios Winston Salem-University Parkway
Pilot Mountain Glamping Resort

Pilot Mountain Glamping Resort

4 out of 5
1051 E Old Phillips Rd Pinnacle NC
$176 nightly
The price is $198 total per night from Nov 4 to Nov 5
$198 total
Nov 4 - Nov 5
Total with taxes and fees
Pilot Mountain Glamping Resort
Comfort Inn Mount Airy

Comfort Inn Mount Airy

2.5 out of 5
1293 Newsome Street Mount Airy NC
Fully refundable
$93 nightly
The price is $105 total per night from Nov 22 to Nov 23
$105 total
Nov 22 - Nov 23
Total with taxes and fees
Comfort Inn Mount Airy
See all 504 properties in Westfield
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 Westfield Vacation Packages

Westfield Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Westfield vacation package cost?
You'll find cheap prices from $628 on Expedia for your Westfield getaway. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Westfield costs.
What are the cheapest months to go to Westfield?
If you're hoping to score a cheap Westfield vacation package, consider planning a trip in November, December and January. You'll typically find better rates on flights and accommodations during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Westfield?
Typically, a handful of days is enough to check out the top attractions during your Westfield vacation. However, if you want to have time to unwind or take day trips, consider extending your trip.
How to find the best Westfield package deals?
Use Expedia's filters to find some fabulous Westfield 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 escape for midweek, or look for Westfield package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Westfield vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component separately. And you'll still get the flexibility to create a personalized Westfield vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Westfield?
Secure incredible discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Westfield vacation.
Does Expedia offer Book Now, Pay Later Westfield vacation packages?
If you're anything like us, you love traveling the world but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Westfield break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.