Winston Vacations from $599

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    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

The Latest Winston vacation packages

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

Creekside Inn

2.5 out of 5
Price was $1,449, price is now $599 per person
$599
per person
Apr 29 - May 4
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
7.8/10 Good! (1,027 reviews)
Good location. Beds were uncomfortable and pillows were very hard. The worse part was, you could hear right thru the walls. I could hear the people in the neighboring room. Had a hard time sleeping due to the noise. I would not stay here again.

Reviewed on Mar 22, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was $4,907, price is now $2,072 per person
$2,072
per person
May 30 - Jun 3
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
5.8/10 (321 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 2026

The Deuce's Wild at Signature Hotel

The Deuce's Wild at Signature Hotel

4 out of 5
Save 100% on your flight
Price was $1,246, price is now $643 per person
$643
per person
May 3 - May 9
found 20 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Las Vegas (LAS)
No reviews
One Bedroom | 1.5 Baths & Living Room | Jet Tub – Palms Place StripSuite

One Bedroom | 1.5 Baths & Living Room | Jet Tub – Palms Place StripSuite

4.5 out of 5
Price was $2,440, price is now $1,282 per person
$1,282
per person
May 28 - Jun 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Las Vegas (LAS)
7/10 Good! (2 reviews)
Staff was awesome and helpful

Reviewed on Sep 2, 2025

SIRTAJ - Beverly Hills

SIRTAJ - Beverly Hills

4 out of 5
South of Wilshire
Save 100% on your flight
Price was $1,132, price is now $607 per person
$607
per person
May 29 - Jun 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Los Angeles (LAX)
8.2/10 Very Good! (1,012 reviews)
Nice room for the price. Price has gone up recently making it not my next choice.

Reviewed on Mar 19, 2026

Don't see what you're looking for?
See all available trips from Columbus to Winston
View all trips

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
$77 nightly
The price is $85 total per night from Mar 29 to Mar 30
$85 total
Mar 29 - Mar 30
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
don't know

Reviewed on Mar 23, 2026

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
$70 nightly
The price is $77 total per night from Mar 31 to Apr 1
$77 total
Mar 31 - Apr 1
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
I booked this room at ths last minute. I didn't realize it was a smoking room. I couldn't get a refund. The room smelled horrible. It's my fault, but it was disgusting

Reviewed on Mar 20, 2026

SureStay Hotel by Best Western Cameron
Days Inn by Wyndham Cameron

Days Inn by Wyndham Cameron

2 out of 5
601 E. Bryan Road Cameron MO
7.6/10 Good! (846 reviews)
The room was clean and everything was in working order. The staff was friendly, professional and helpful. A great stay.

Reviewed on Mar 22, 2026

Get rates
Days Inn by Wyndham Cameron
See all 50 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Winston vacation package cost?
You'll find cheap prices from $599 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.