Winston Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

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$100 per night from 1 Dec to 2 Dec
S$100
includes taxes & fees
1 Dec - 2 Dec
8.2/10 Very Good! (1,245 reviews)
"The fresh baked cookies every afternoon."

Reviewed on 27 Nov,2024

Baymont by Wyndham Helena
Hampton Inn Helena
Hampton Inn Helena
2.5 out of 5
725 Carter Dr, Helena, MT
Fully refundableReserve now, pay when you stay
The price is S$146 per night from 1 Dec to 2 Dec
S$146
includes taxes & fees
1 Dec - 2 Dec
8.8/10 Excellent! (593 reviews)
"This hotel was very clean. Even the pet room we had smelled good and not like heavy carpet cleaner hiding cat pee. They also didn’t over charge us for having 2 dogs. The breakfast was amazing! I never find breakfast options so good at this price point. They even had a little snack area if you wanted ..."

Reviewed on 26 Nov,2024

Hampton Inn Helena
La Quinta Inn & Suites by Wyndham Helena
La Quinta Inn & Suites by Wyndham Helena
2.5 out of 5
701 Washington St, Helena, MT
Fully refundableReserve now, pay when you stay
The price is S$132 per night from 1 Dec to 2 Dec
S$132
includes taxes & fees
1 Dec - 2 Dec
7.4/10 Good! (1,002 reviews)
"Nice size room and really quiet and affordable"

Reviewed on 26 Nov,2024

La Quinta Inn & Suites by Wyndham Helena
See all 191 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?
From as little as , you can tailor your Winston package. Simply combine hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Winston?
Our Winston holiday packages promise plenty of savings for the savvy explorer. For the best deals, simply bundle your flights, hotels and extras (such as activities) into an affordable package. But low prices are just the beginning of your next amazing adventure. When you book with Expedia, and you’ll have over 550 air carriers and 1,000,000 hotel options across the globe to select from. No matter your budget, there’s a package here just for you.
How far in advance should I book my Winston holiday?
Travellers are normally able to browse international fares on Expedia within 12 months of departure. Booking at the last minute? With a bit of luck, it’s still possible to score an affordable ticket just weeks before your flight.
What does an Expedia Winston travel package include?
Choose from any combination of hotels, flights and rental cars. Once you’ve made your booking, you can add the fun stuff like activities and experiences. Want to pick your fare class? That’s possible too. The choice is yours when it comes to crafting your perfect Winston trip.
What should I know before booking a Winston travel package?
Discover deals that suit your budget with an Expedia package. Airfares, hotels, rental cars — we have them all. You’ll save loads just by combining your bookings. Whether you’re embarking on a winter adventure or sipping cocktails on a beach, your perfect holiday is just a few clicks away.
Can I choose my airline with a Winston Expedia holiday package?
With a holiday package, you’re in control. Whether you’re hoping to fly to Winston in coach or business class, simply choose from the available airline options. Expedia has access to more than 550 partner airlines all over the world.
If I'm not able to travel, can I cancel my Winston holiday package?
Because we know life can throw you a few curveballs, the answer is yes. To find out more, check out our Customer Service Portal. But generally speaking, if you’ve booked your Winston holiday package in the last 24 hours, you may be able to change or cancel it for free. Your airline, hotel or car rental company may impose a fee if you made your booking a while ago.

* 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.