Winston Vacations from $643

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The Latest Winston vacation packages

Price found within the past 48 hours. Click for updated prices.
Americas Best Value Inn & Suites Helena

Americas Best Value Inn & Suites Helena

2 out of 5
Price was $704, price is now $643 per person
$643
per person
Oct 22 - Oct 27
found 20 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to Helena (HLN)
5/10 (813 reviews)
Very polite and professional staff room was very clean. Great location

Reviewed on Aug 27, 2025

Home2 Suites by Hilton Helena

Home2 Suites by Hilton Helena

3 out of 5
Price was $855, price is now $766 per person
$766
per person
Oct 22 - Oct 27
found 20 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to Helena (HLN)
9/10 Wonderful! (716 reviews)
No shower curtain??!

Reviewed on Aug 13, 2025

Baymont by Wyndham Helena

Baymont by Wyndham Helena

2.5 out of 5
Price was $788, price is now $706 per person
$706
per person
Oct 22 - Oct 27
found 20 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to Helena (HLN)
8/10 Very Good! (1,544 reviews)
This is a great, convenient place to stay.

Reviewed on Aug 29, 2025

Fairfield by Marriott Inn & Suites Helena North

Fairfield by Marriott Inn & Suites Helena North

3.5 out of 5
Price was $811, price is now $731 per person
$731
per person
Oct 22 - Oct 27
found 20 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to Helena (HLN)
7.8/10 Good! (100 reviews)
Room was clean and spacious enough. The staff were friendly and helpful. Good breakfast options. Some of the common areas need the carpets and tiles replaced. The gym was decent but a bit small and there were some weights missing. Pool and hot tub were decent. I'd stay there again, it just needed some love here and there.

Reviewed on Aug 9, 2025

Holiday Inn Express Hotel & Suites Helena by IHG

Holiday Inn Express Hotel & Suites Helena by IHG

2.5 out of 5
Price was $867, price is now $802 per person
$802
per person
Oct 22 - Oct 27
found 20 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to Helena (HLN)
9.2/10 Wonderful! (734 reviews)
It was a very nice property. Most of the staff was exceptional. The green haired staff member, was just like the one in the movie. She was not at all helpful!! The others were so kind and willing to help. It was very clean. The breakfast was very nice, great selection, great staff. It was also nice to be able to get coffee all day. Very convient to stores and resturants. Would stay here again.

Reviewed on Aug 20, 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
$98 nightly
The price is $108 total per night from Sep 7 to Sep 8
$108 total
Sep 7 - Sep 8
Total with taxes and fees
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
$84 nightly
The price is $93 total per night from Sep 21 to Sep 22
$93 total
Sep 21 - Sep 22
Total with taxes and fees
7.8/10 Good! (1,465 reviews)
"I had a nice evening at the hotel, was welcomed very kindly in the evening and helped readily with checkout and a logistical question I had. Grateful to the hotel and cleaning staff!"

Reviewed on Aug 24, 2025

Baymont by Wyndham Helena
Days Inn by Wyndham Helena

Days Inn by Wyndham Helena

2 out of 5
2001 Prospect Ave, Helena, MT
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $95 total per night from Sep 21 to Sep 22
$95 total
Sep 21 - Sep 22
Total with taxes and fees
7.6/10 Good! (1,005 reviews)
"U"

Reviewed on Aug 25, 2025

Days Inn by Wyndham Helena
See all 207 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.

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Frequently asked questions

How much does a Winston vacation package cost?
You'll find cheap prices from $643 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.