Winston Vacations from $1,776

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 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

The Latest Winston vacation packages

Price found within the past 48 hours. Click for updated prices.
Best Western Helena/Capitol Hotel

Best Western Helena/Capitol Hotel

2.5 out of 5
Price was $1,826, price is now $1,776 per person
$1,776
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Lansing (LAN) to Helena (HLN)
16/10 Exceptional! (1,001 reviews)
Chris was very helpful, courteous and friendly at the front desk. Room is excellent. We're glad we chose to stay here.

Reviewed on Nov 13, 2025

Best Western Premier Helena Great Northern Hotel

Best Western Premier Helena Great Northern Hotel

3 out of 5
Price was $1,929, price is now $1,851 per person
$1,851
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Lansing (LAN) to Helena (HLN)
18.8/10 Exceptional! (842 reviews)
The doors to the rooms slam very hard unless a guest carefully shuts them. Also, the doors have a space underneath through which you can see light from the hallway coming through at night — and also, of course, noise from the hallway. They need to work on the doors.

Reviewed on Nov 22, 2025

Home2 Suites by Hilton Helena

Home2 Suites by Hilton Helena

3 out of 5
Price was $1,913, price is now $1,836 per person
$1,836
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Lansing (LAN) to Helena (HLN)
18/10 Exceptional! (738 reviews)
Staff was great. Had an issue with a room that had a doior open to another room. Upgraded us free to a suite instead. Wasnt necessary but nice.

Reviewed on Nov 18, 2025

Residence Inn by Marriott Helena

Residence Inn by Marriott Helena

3 out of 5
Price was $1,862, price is now $1,808 per person
$1,808
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Lansing (LAN) to Helena (HLN)
18.8/10 Exceptional! (503 reviews)
Super quiet and comfortable I would stay here anytime

Reviewed on Nov 19, 2025

Fairfield by Marriott Inn & Suites Helena North

Fairfield by Marriott Inn & Suites Helena North

3.5 out of 5
Price was $1,834, price is now $1,788 per person
$1,788
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Lansing (LAN) to Helena (HLN)
16/10 Exceptional! (114 reviews)
breakfast was always good! love the staff and the GM. We will be staying here often through out the year.

Reviewed on Nov 10, 2025

Don't see what you're looking for?
See all available trips from Columbus to Winston
View all trips

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now

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
$67 nightly
The price is $74 total per night from Dec 2 to Dec 3
$74 total
Dec 2 - Dec 3
Total with taxes and fees
7.4/10 Good! (1,005 reviews)
Excellent room, very clean and spacious and the front desk staff was friendly and helpful.

Reviewed on Nov 13, 2025

La Quinta Inn & Suites 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
$91 nightly
The price is $101 total per night from Nov 30 to Dec 1
$101 total
Nov 30 - Dec 1
Total with taxes and fees
8.6/10 Excellent! (809 reviews)
wonderful

Reviewed on Nov 17, 2025

Hampton Inn 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
$59 nightly
The price is $65 total per night from Nov 23 to Nov 24
$65 total
Nov 23 - Nov 24
Total with taxes and fees
7.8/10 Good! (1,630 reviews)
yes However the window on the first floor room 101 was cracked and just taped. It needs to be repaired.

Reviewed on Nov 18, 2025

Baymont by Wyndham Helena
See all 208 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.

Find the Best Winston Vacation Packages

Winston Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Helena Regional Airport (HLN)

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Winston vacation package cost?
You'll find cheap prices from $1,776 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?
July, August and December are great times to look for cheap Winston vacation packages. Opting to travel in less busy months means you'll typically find reduced prices on flights and hotels.
How many days is enough for Winston?
The ideal length of your Winston vacation depends on what you'd like to see and do. Usually, a few days to a week will give you enough time to hit all the major attractions and discover some hidden gems 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.
Does Expedia offer Book Now, Pay Later Winston vacation packages?
Your Winston trip is meant to be an escape from your daily routine, not a source of money-related stress. So to give you a bit more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.