Winston Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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Winston Hotel Deals

La Quinta Inn & Suites by Wyndham Helena

La Quinta Inn & Suites by Wyndham Helena

3 out of 5
701 Washington St, Helena, MT
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Aug 3 to Aug 4
CA $159
CA $175 total
Aug 3 - Aug 4
includes taxes & fees
7.4/10 Good! (1,026 reviews)
"We came to Helena for an Irish sports event and the Celtic Festival the next day. La Quinta was in a great location for that. The staff were topnotch. Thanks."

Reviewed on Jul. 24, 2025

La Quinta Inn & Suites by Wyndham Helena
Baymont by Wyndham Helena

Baymont by Wyndham Helena

2.5 out of 5
750 N Fee St, Helena, MT
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Aug 24 to Aug 25
CA $142
CA $157 total
Aug 24 - Aug 25
includes taxes & fees
8/10 Very Good! (1,513 reviews)
"Been staying here for years and always been excellent."

Reviewed on Jul. 25, 2025

Baymont by Wyndham Helena
Americas Best Value Inn & Suites Helena

Americas Best Value Inn & Suites Helena

2 out of 5
800 N. Oregon Street, Helena, MT
Fully refundable
The price is CA $96 per night from Aug 4 to Aug 5
CA $96
CA $106 total
Aug 4 - Aug 5
includes taxes & fees
4.8/10 (786 reviews)
"Kind of off the beaten path. End of July and thebpiol is still closed for winter."

Reviewed on Jul. 21, 2025

Americas Best Value Inn & Suites Helena
See all 202 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.
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Frequently asked questions

How much does a Winston vacation package cost?
You'll find cheap prices on Expedia for your Winston break. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Winston costs.
What are the cheapest months to go to Winston?
If you're looking to snag a cheap Winston vacation package, consider visiting in January, February and November. You'll usually find better rates on hotels and flights during these quieter months — perfect for budget-conscious travellers.
How many days is enough for Winston?
The ideal duration for your Winston vacation depends on what you'd like to see and do. Typically, a few days to a week will give you enough time to go to all the leading sights and explore some hidden gems along the way.
How to find the best Winston package deals?
Use Expedia's filter tool to help you find some tempting Winston package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Winston package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Winston vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component individually. And you'll still enjoy the flexibility to create a customized Winston vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Winston?
Land fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Winston getaway.
How to plan a trip to Winston?

  1. Choose when to get away: Check your diary and get packing. Your preferred season and the available activities will also help you decide when to escape to Winston.
  2. Budget wisely: In addition to the price of your accommodations, you'll need to consider other expenses too. These include flights, food and transportation. Also, set aside some extra funds for unexpected costs that could arise during your trip to Winston.
  3. Determine how many days away: Start by compiling a list of the attractions you'd like to get to in Winston. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your airfare and accommodations: Once you've nailed down your trip dates and duration, lock in the perfect Winston vacation package for you.

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