Winston Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Top Winston Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Margaritaville Hotel Kansas City

Margaritaville Hotel Kansas City

4 out of 5
I-435 West
Price was CA $1,617, price is now CA $1,448 per person
CA $1,448
per person
Dec 19 - Dec 22
found 5 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kansas City (MCI)
9.2/10 Wonderful! (1,007 reviews)
Excelentes condiciones muy confortable y tropical me encantó

Reviewed on Nov 3, 2026

Chateau Avalon Hotel & Spa

Chateau Avalon Hotel & Spa

3.5 out of 5
I-435 West
Price was CA $2,618, price is now CA $2,327 per person
CA $2,327
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kansas City (MCI)
8.2/10 Very good! (1,002 reviews)

Ameristar Casino Hotel Kansas City

Ameristar Casino Hotel Kansas City

4 out of 5
Birmingham Bottoms
Price was CA $2,241, price is now CA $2,019 per person
CA $2,019
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kansas City (MCI)
8.6/10 Excellent! (1,205 reviews)

La Quinta Inn & Suites by Wyndham Kansas City Beacon Hill

La Quinta Inn & Suites by Wyndham Kansas City Beacon Hill

3 out of 5
Beacon Hills
Price was CA $2,161, price is now CA $1,951 per person
CA $1,951
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kansas City (MCI)
8.8/10 Excellent! (1,785 reviews)

The Elms Hotel & Spa, a Destination by Hyatt Hotel

The Elms Hotel & Spa, a Destination by Hyatt Hotel

4 out of 5
Price was CA $1,642, price is now CA $1,484 per person
CA $1,484
per person
Dec 19 - Dec 22
found 5 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kansas City (MCI)
8.8/10 Excellent! (1,005 reviews)

Ready to book your vacation to Winston?

 

Choose your dates

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
The price is CA $109 per night from Nov 10 to Nov 11
CA $109
CA $120 total
Nov 10 - Nov 11
includes taxes & fees
8/10 Very good! (1,000 reviews)
"The building is slowing being renovated. Beautiful view of a large garden and doorstep parking. Our room had not been completely refitted with both bedside tables and the new desk, but we are looking forward to seeing how the room appears next stay. Note to self, get to breakfast a little earlier ..."

Reviewed on Nov 3, 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
The price is CA $109 per night from Dec 1 to Dec 2
CA $109
CA $120 total
Dec 1 - Dec 2
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"We stayed in an accessible room and that was great with regard to bars and accessibility to the toilet, etc. The bathroom was a bit rough around the edges as the carpentry did not look quite finished. The staff was very friendly. We only have one complaint. They have a rule that you cannot leave ..."

Reviewed on Nov 2, 2026

Red Roof Inn Cameron
Quality Inn Cameron

Quality Inn Cameron

2.5 out of 5
1803 Comfort Ln Cameron MO
Fully refundable
The price is CA $142 per night from Dec 3 to Dec 4
CA $142
CA $157 total
Dec 3 - Dec 4
includes taxes & fees
Quality Inn Cameron
See all 69 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Winston vacation package cost?
Offering excellent value package deals from CA $1,448 on Expedia, you'll be surprised at how little a vacation to Winston costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winston?
You can usually find lower prices and better availability in January, February and November. Check out our cheap Winston vacation packages and you could get some great off-season discounts.
How many days is enough for Winston?
With a well-organized itinerary, you can easily visit the most popular Winston attractions in a handful of days. But if you'd like to discover hidden spots or go on day tours, think about booking your Winston vacation for longer.
How to find the best Winston package deals?
Landing a cheap Winston package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget, add some filters and see what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most affordable Winston package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Winston vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking hotels and flights separately. Better still, you can personalize your Winston escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Winston?
If you have your Winston travel dates finalized, book early to snap up some incredible deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Winston?

  1. Choose when to travel: Check your schedule and get packing. Your preferred time of year and the type of activities available will also help you decide when to visit Winston.
  2. Work out your budget: Ensure you have enough money to cover everything from food and transportation to experiences and flights. Your hotel will likely be the biggest expense during your trip to Winston.
  3. Decide your trip length: Consider how long you'd like to spend discovering Winston. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to pick a Winston vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.