Winston Holidays

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    Save up to S$134 when you book a flight and hotel together*
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    Plan, book, and manage your trip all in one place

Top hotels in Winston

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 S$137 per night from 29 Jun to 30 Jun
S$137
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (1,466 reviews)
"Friendly staff. Quick check in. Quiet neighborhood"

Reviewed on 21 Jun, 2025

Baymont by Wyndham Helena
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 S$151 per night from 23 Jun to 24 Jun
S$151
23 Jun - 24 Jun
includes taxes & fees
7.4/10 Good! (1,009 reviews)
"I liked the clean breakfast area with numerous options. The staff kept everything well stocked and very clean. Also enjoyed having coffee available anytime. Plus staff were always very friendly and helpful. I was n Helena for my mothers funeral and it was very emotional but your staff were ..."

Reviewed on 21 Jun, 2025

La Quinta Inn & Suites 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 S$89 per night from 29 Jun to 30 Jun
S$89
29 Jun - 30 Jun
includes taxes & fees
4.8/10 (733 reviews)
"Ok"

Reviewed on 10 Jun, 2025

Americas Best Value Inn & Suites Helena
See all 201 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.

Frequently asked questions

How much does a Winston holiday package cost?
You'll find cheap prices on Expedia for your Winston escape. However, factors like the season, choice of hotel and length of stay will influence how much your holiday 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 holiday packages and you could land some great off-season discounts.
How many days is enough for Winston?
The ideal length for your Winston holiday 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 holiday as a package?
An Expedia holiday package could land you considerable savings when compared to arranging flights and hotels separately. Better still, you can customise 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 holiday 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 accommodation 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 holiday 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.