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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Top Winston Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Helena
Home2 Suites by Hilton Helena
Holiday Inn Express Hotel & Suites Helena, an IHG Hotel

Ready to book your vacation to Winston?

 

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Winston Hotel Deals

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 $95 per night from Mar. 2 to Mar. 3
CA $95
CA $105 total
includes taxes & fees
Mar 2 - Mar 3
8.2/10 Very Good! (1,335 reviews)
"It was a decent hotel with a good price"

Reviewed on Feb. 26, 2025

Baymont by Wyndham Helena
Home2 Suites by Hilton Helena
Home2 Suites by Hilton Helena
3 out of 5
3325 N Sanders St, Helena, MT
Fully refundableReserve now, pay when you stay
The price is CA $171 per night from Mar. 16 to Mar. 17
CA $171
CA $187 total
includes taxes & fees
Mar 16 - Mar 17
9/10 Wonderful! (656 reviews)
"To good Clean n spacious rooms n very comfortable"

Reviewed on Feb. 21, 2025

Home2 Suites by Hilton Helena
Days Inn by Wyndham Helena
Days Inn by Wyndham Helena
2 out of 5
2001 Prospect Ave, Helena, MT
Fully refundableReserve now, pay when you stay
The price is CA $102 per night from Mar. 3 to Mar. 4
CA $102
CA $121 total
includes taxes & fees
Mar 3 - Mar 4
7.8/10 Good! (1,000 reviews)
"Parking lot was essentially a slip and slide. Showed very little care was taken into consideration for the traveling clientele that they are supposedly providing a safe place to sleep."

Reviewed on Feb. 23, 2025

Days Inn by Wyndham Helena
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.

Frequently asked questions

How much does a Winston vacation package cost?
You’ll find cheap prices from CA $864 on Expedia for your Winston escape. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Winston costs.
What are the cheapest months to go to Winston?
You can generally find reduced prices and better availability in January, February and November. Check out our cheap Winston vacation packages and you could land some great off-season discounts.
How many days is enough for Winston?
The ideal length for your Winston vacation depends on what you’d like to do. Generally, a few days to a week will give you plenty of time to hit all the main attractions and explore some hidden treasures along the way.
How to find the best Winston package deals?
Begin your search for a Winston package deal by entering your destination and preferred trip dates under our “Packages” tab. Then select some filters, like “Property type” and “Amenities,” to fine-tune the results to your exact needs. You can also sort by “Package discount” and discover offers that come with big savings. If you don’t find the perfect Winston package deal right away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winston escape underway.
Is it cheaper to book a Winston vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and hotels separately. Better still, you can customize your Winston escape to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Winston?
Score fantastic discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Winston adventure.
How to plan a trip to Winston?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Winston.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and dining out to flights and experiences. Your accommodations will likely be the largest expense during your trip to Winston.
  3. Decide how long to go for: Now that you know more about Winston, you can work out the right length of your break. Put together a draft plan and allocate enough time for all the things you want to do.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that’s left is to choose 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.