Winston Vacations from $476

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The Latest Winston vacation packages

Price found within the past 48 hours. Click for updated prices.
Candlewood Suites Northeast Kansas City by IHG

Candlewood Suites Northeast Kansas City by IHG

2.5 out of 5
Winnetonka
Price was $627, price is now $476 per person
$476
per person
Sep 11 - Sep 15
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Kansas City (MCI)
8.6/10 Excellent! (327 reviews)
Thank you to all the employees. They were super nice and helpful.

Reviewed on Jul 6, 2026

Ameristar Casino Hotel Kansas City

Ameristar Casino Hotel Kansas City

4 out of 5
Birmingham Bottoms
Save 100% on your flight
Price was $833, price is now $526 per person
$526
per person
Sep 11 - Sep 15
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Kansas City (MCI)
8.6/10 Excellent! (1,124 reviews)
property was clean and well maintained. Large variety of slots were available

Reviewed on Jul 6, 2026

The Inn at Meadowbrook

The Inn at Meadowbrook

4 out of 5
Price was $1,147, price is now $834 per person
$834
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Kansas City (MCI)
9.8/10 Exceptional! (448 reviews)
Everything was just amazing!!

Reviewed on Jun 5, 2026

The Elms Hotel & Spa, a Destination by Hyatt Hotel

The Elms Hotel & Spa, a Destination by Hyatt Hotel

4 out of 5
Price was $847, price is now $643 per person
$643
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Kansas City (MCI)
8.8/10 Excellent! (1,005 reviews)
We enjoyed our overnight stay. Had a nice time at the pool.

Reviewed on Jul 6, 2026

Origin Kansas City Riverfront, a Wyndham Hotel

Origin Kansas City Riverfront, a Wyndham Hotel

3 out of 5
Price was $842, price is now $662 per person
$662
per person
Sep 11 - Sep 15
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Kansas City (MCI)
9.6/10 Exceptional! (721 reviews)
Beautiful hotel, great staff, clean

Reviewed on Jun 30, 2026

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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
$75 nightly
The price is $83 total per night from Aug 2 to Aug 3
$83 total
Aug 2 - Aug 3
Total with taxes and fees
8.6/10 Excellent! (1,005 reviews)
"Beautiful, clean room. The motel experience was different but easy. The breakfast was good and the staff there in the morning was nice and helpful."

Reviewed on Jul 7, 2026

Red Roof Inn Cameron
Quality Inn Cameron

Quality Inn Cameron

2.5 out of 5
1803 Comfort Ln Cameron MO
Fully refundable
$113 nightly
The price is $125 total per night from Aug 2 to Aug 3
$125 total
Aug 2 - Aug 3
Total with taxes and fees
8.6/10 Excellent! (678 reviews)
"The clerk at the front desk was very friendly. Our room was clean. The pillows on the bed were terrible. Very soft and very lumpy. The bathroom door was too big for the doorway."

Reviewed on Jul 6, 2026

Quality Inn Cameron
Super 8 by Wyndham Cameron

Super 8 by Wyndham Cameron

2 out of 5
1710 N Walnut St Cameron MO
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $98 total per night from Jul 17 to Jul 18
$98 total
Jul 17 - Jul 18
Total with taxes and fees
8.4/10 Very Good! (682 reviews)
"We reserved a multi bed room and it was amazing. These types of rooms are rare stateside and it was delightful. Enough beds and space for our whole family. Nice to spread out after being cooped up in a car. Dave was so nice and kind. Room was very clean. Would 100% stay in this place again."

Reviewed on Jul 2, 2026

Super 8 by Wyndham Cameron
See all 64 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 $476 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.