Winston Vacations from $669

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The Latest Winston vacation packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Helena

Days Inn by Wyndham Helena

2 out of 5
Price was $721, price is now $669 per person
$669
per person
Mar 24 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Helena (HLN)
7.8/10 Good! (1,004 reviews)
The staff were very nice. Can't beat the free breakfast.

Reviewed on Jan 8, 2026

Oddfellow Inn & Farm

Oddfellow Inn & Farm

2.5 out of 5
Price was $1,735, price is now $1,357 per person
$1,357
per person
Mar 24 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Helena (HLN)
8.2/10 Very Good! (73 reviews)
Fairfield by Marriott Inn & Suites Helena North

Fairfield by Marriott Inn & Suites Helena North

3.5 out of 5
Price was $747, price is now $679 per person
$679
per person
Mar 24 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Helena (HLN)
8/10 Very Good! (114 reviews)
An excellent hotel, great staff, and a good complimentary breakfast.

Reviewed on Dec 11, 2025

Holiday Inn Express Hotel & Suites Helena by IHG

Holiday Inn Express Hotel & Suites Helena by IHG

2.5 out of 5
Price was $729, price is now $681 per person
$681
per person
Mar 24 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Helena (HLN)
9.2/10 Wonderful! (766 reviews)
Spotless room and a great breakfast!

Reviewed on Dec 20, 2025

Delta Hotels by Marriott Helena Colonial

Delta Hotels by Marriott Helena Colonial

3 out of 5
Price was $798, price is now $747 per person
$747
per person
Mar 24 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Helena (HLN)
8.2/10 Very Good! (608 reviews)
Rooms clean, I love how well it’s set up if you bring your dog. Service wasn’t fabulous the younger lady at the front desk was quite stand offish but the restaurant has pretty good food

Reviewed on Nov 5, 2025

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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
$77 nightly
The price is $85 total per night from Jan 12 to Jan 13
$85 total
Jan 12 - Jan 13
Total with taxes and fees
7.4/10 Good! (1,010 reviews)
Staff very friendly

Reviewed on Jan 4, 2026

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
$68 nightly
The price is $76 total per night from Jan 11 to Jan 12
$76 total
Jan 11 - Jan 12
Total with taxes and fees
7.8/10 Good! (1,641 reviews)
After long day of driving it was nice to be greeted by a smile and very friendly clerk at front desk. Very thorough with what was offered.. rooms clean , the fan woke me up lots but beds comfy

Reviewed on Jan 7, 2026

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
$78 nightly
The price is $86 total per night from Jan 15 to Jan 16
$86 total
Jan 15 - Jan 16
Total with taxes and fees
8.6/10 Excellent! (842 reviews)
Staff was courteous and room was very clean!

Reviewed on Jan 4, 2026

Hampton Inn Helena
See all 209 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)

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Frequently asked questions

How much does a Winston vacation package cost?
You'll find cheap prices from $669 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.