Winston Vacations from $171

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The Latest Winston vacation packages

Price found within the past 48 hours. Click for updated prices.
Planet Hollywood Resort & Casino

Planet Hollywood Resort & Casino

4 out of 5
Las Vegas Strip
Save 100% on your flight
Price was $380, price is now $171 per person
$171
per person
Dec 8 - Dec 11
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Las Vegas (LAS)
8/10 Very Good! (18,795 reviews)
Our room was very clean and i had no problems checking in. All the staff was very nice and helpful, i would definitely stay here again.

Reviewed on Oct 13, 2025

Paris Las Vegas Resort & Casino

Paris Las Vegas Resort & Casino

4 out of 5
Las Vegas Strip
Price was $951, price is now $219 per person
$219
per person
Dec 8 - Dec 11
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Las Vegas (LAS)
8/10 Very Good! (24,028 reviews)
There is everything you gonna need for. I’ll definitely come back.

Reviewed on Oct 13, 2025

Fontainebleau Las Vegas

Fontainebleau Las Vegas

5 out of 5
Las Vegas Strip
Price was $957, price is now $329 per person
$329
per person
Dec 8 - Dec 11
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Las Vegas (LAS)
9.4/10 Exceptional! (12,304 reviews)
Great amenities, professional staff, very new and chic!

Reviewed on Oct 14, 2025

Horseshoe Las Vegas

Horseshoe Las Vegas

4 out of 5
Las Vegas Strip
Save 100% on your flight
Price was $557, price is now $240 per person
$240
per person
Dec 8 - Dec 11
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Las Vegas (LAS)
7.8/10 Good! (10,708 reviews)
Within easy reach of the strip. Unaware of the US$50 tourist tax for the area.

Reviewed on Oct 13, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $15,260, price is now $7,157 per person
$7,157
per person
Dec 20 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Miami (MIA)
8/10 Very Good! (1 review)
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Winston Hotel Deals

Red Roof Inn Cameron

Red Roof Inn Cameron

2 out of 5
501 Northland Drive, Cameron, MO
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $95 total per night from Nov 2 to Nov 3
$95 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (1,006 reviews)
"Clean and comfy"

Reviewed on Oct 8, 2025

Red Roof Inn Cameron
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
$78 nightly
The price is $86 total per night from Oct 20 to Oct 21
$86 total
Oct 20 - Oct 21
Total with taxes and fees
8.2/10 Very Good! (1,001 reviews)
"Breakfast was good"

Reviewed on Oct 3, 2025

SureStay Hotel by Best Western Cameron
Days Inn by Wyndham Cameron

Days Inn by Wyndham Cameron

2 out of 5
601 E. Bryan Road, Highway 36 and 69, Cameron, MO
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $82 total per night from Oct 28 to Oct 29
$82 total
Oct 28 - Oct 29
Total with taxes and fees
7.6/10 Good! (797 reviews)
"No elevs. Stairs to second floor. Ck in clerk distracted. Morning clerk engaging."

Reviewed on Oct 9, 2025

Days Inn by Wyndham Cameron
See all 53 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.

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 $171 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.