Winston Vacations from $565

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The Latest Winston vacation packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Helena

Super 8 by Wyndham Helena

2 out of 5
per person
Aug 25 - Sep 1
found 4 hours ago
Roundtrip flight included
Seattle (SEA) to Helena (HLN)
5.4/10 (1,005 reviews)
Old and construction debris on stairs

Reviewed on Jul 10, 2025

Baymont by Wyndham Helena

Baymont by Wyndham Helena

2.5 out of 5
per person
Aug 25 - Sep 1
found 4 hours ago
Roundtrip flight included
Seattle (SEA) to Helena (HLN)
8.2/10 Very Good! (1,479 reviews)
It was not bad, my only concern was the long walk till you get to your room

Reviewed on Jul 11, 2025

Fairfield by Marriott Inn & Suites Helena North

Fairfield by Marriott Inn & Suites Helena North

3.5 out of 5
per person
Aug 25 - Sep 1
found 4 hours ago
Roundtrip flight included
Seattle (SEA) to Helena (HLN)
8/10 Very Good! (93 reviews)
The room was nice and clean. The staff was friendly and helpful. Only thing that could use some work is the windows need cleaning

Reviewed on Jun 29, 2025

Comfort Suites Helena Airport

Comfort Suites Helena Airport

2.5 out of 5
per person
Aug 25 - Sep 1
found 4 hours ago
Roundtrip flight included
Seattle (SEA) to Helena (HLN)
9/10 Wonderful! (1,003 reviews)
They switch our room to accommodate my 95 yr old mother. They were so nice. Roo. Was great

Reviewed on Jul 11, 2025

Holiday Inn Express Hotel & Suites Helena by IHG

Holiday Inn Express Hotel & Suites Helena by IHG

2.5 out of 5
per person
Aug 25 - Sep 1
found 4 hours ago
Roundtrip flight included
Seattle (SEA) to Helena (HLN)
9.2/10 Wonderful! (714 reviews)
Excellent hotel. Beds were comfortable, staff was kind and helpful, breakfast had many selections. I will definitely stay again.

Reviewed on Jul 6, 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
$152 nightly
The price is $166 total per night from Jul 20 to Jul 21
$166 total
Jul 20 - Jul 21
Total includes taxes and fees
7.4/10 Good! (1,008 reviews)
"Convevenient to highway"

Reviewed on Jul 11, 2025

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
$103 nightly
The price is $113 total per night from Aug 3 to Aug 4
$113 total
Aug 3 - Aug 4
Total includes taxes and fees
8/10 Very Good! (1,490 reviews)
"It was not bad, my only concern was the long walk till you get to your room"

Reviewed on Jul 11, 2025

Baymont by Wyndham Helena
Super 8 by Wyndham Helena
Super 8 by Wyndham Helena
2 out of 5
2200 11th Ave, Helena, MT
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $102 total per night from Jul 31 to Aug 1
$102 total
Jul 31 - Aug 1
Total includes taxes and fees
5.4/10 (1,011 reviews)
"Location is good, room is clean and enough space. However, the air conditioner seems old fashioned and loud noise"

Reviewed on Jul 10, 2025

Super 8 by Wyndham 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.

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 $565 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.