Winston Vacations from $590

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The Latest Winston vacation packages

Price found within the past 48 hours. Click for updated prices.
MirabileCondoDwntown MIA Brickell w PRKG

MirabileCondoDwntown MIA Brickell w PRKG

5 out of 5
Downtown Miami
Price was $1,480, price is now $590 per person
$590
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
New York (LGA) to Miami (MIA)
2/10 (2 reviews)
Encore Inn Inglewood

Encore Inn Inglewood

2.5 out of 5
Lockhaven
Price was $1,841, price is now $593 per person
$593
per person
Jul 2 - Jul 6
found 24 hours ago
Roundtrip flight included
Dallas (DAL) to Los Angeles (LAX)
6.4/10 (159 reviews)
Clean room w/ a shower.

Reviewed on Jan 2, 2026

Brickell Bay 3318

Brickell Bay 3318

3 out of 5
Brickell
Price was $1,496, price is now $598 per person
$598
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
No reviews
The W - Bayshore Unit 1003

The W - Bayshore Unit 1003

3 out of 5
East Fort Lauderdale
Price was $1,932, price is now $773 per person
$773
per person
Jun 22 - Jun 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
6/10 (2 reviews)
I thoroughly enjoyed my stay at this hotel. The host was incredibly friendly and attentive, and the communication was prompt and efficient. The hotel itself was beautiful, and the staff was incredibly kind and helpful.

Reviewed on May 20, 2026

3BR Pool House Sleeps 8

3BR Pool House Sleeps 8

3 out of 5
Driftwood
Price was $1,638, price is now $682 per person
$682
per person
Jul 6 - Jul 9
found 2 days ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
No reviews
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Winston Hotel Deals

SureStay Hotel by Best Western Cameron

SureStay Hotel by Best Western Cameron

2.5 out of 5
2210 US Highway 36 Cameron MO
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $85 total per night from Jun 7 to Jun 8
$85 total
Jun 7 - Jun 8
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
"the rooms were clean however this place needs to upgrade the Bed mattress, Hard and very thin my back still hurts after sleeping on the mattress"

Reviewed on May 22, 2026

SureStay Hotel by Best Western Cameron
Red Roof Inn Cameron

Red Roof Inn Cameron

2 out of 5
501 Northland Drive Cameron MO
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $102 total per night from Jun 8 to Jun 9
$102 total
Jun 8 - Jun 9
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
"Cool way to check in with the virtual agent. Smooth check in. Nice, well maintained facility."

Reviewed on May 22, 2026

Red Roof Inn Cameron
Quality Inn Cameron

Quality Inn Cameron

2.5 out of 5
1803 Comfort Ln Cameron MO
Fully refundable
$109 nightly
The price is $121 total per night from May 31 to Jun 1
$121 total
May 31 - Jun 1
Total with taxes and fees
8.4/10 Very Good! (657 reviews)
"Clean, Brwakfast was really good."

Reviewed on May 10, 2026

Quality Inn Cameron
See all 57 properties in Winston
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 Winston Vacation Packages

Winston Essential Information

Language
English
Currency
U.S dollars
Top Sights
Gallatin Methodist Church, Cameron Veterans Memorial Golf Glub and Adam-ondi-Ahman

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Frequently asked questions

How much does a Winston vacation package cost?
You'll find cheap prices from $590 on Expedia for your Winston break. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Winston costs.
What are the cheapest months to go to Winston?
If you'd like to score a cheap Winston vacation package, consider planning a trip in December, January and February. You're likely to find lower prices on accommodations and flights during these months — ideal for budget-conscious travelers.
How many days is enough for Winston?
Typically, a handful of days is enough to check out the major sights during your Winston vacation. But if you prefer to have some time to chill out or take day tours, think about extending your itinerary.
How to find the best Winston package deals?
Bagging a cheap Winston package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most pocket-friendly Winston package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Winston vacation as a package?
You can enjoy significant savings on your Winston getaway by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to view some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Winston?
If you're planning a spur-of-the-moment Winston trip, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find incredible deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Winston vacation packages?
Set off on your dream trip to Winston with help from Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait until your next payday — we've teamed up with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans let you spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stick to your budget and snap up travel deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.