Helena Vacations from $491

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The Latest Helena vacation packages

Price found within the past 48 hours. Click for updated prices.
Christmas Mountain Campground

Christmas Mountain Campground

3 out of 5
per person
Sep 25 - Sep 29
found 12 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Madison (MSN)
8.8/10 Excellent! (60 reviews)
Cottage was very nice. Clean and in good condition. Some of the roads need re-paved for bicycle riding, but overall we really enjoyed it. There are a lot of options for activities which is nice

Reviewed on Jul 20, 2025

Bluegreen Odyssey Dells

Bluegreen Odyssey Dells

3.5 out of 5
per person
Sep 25 - Sep 29
found 12 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Madison (MSN)
9.4/10 Exceptional! (141 reviews)
Definitely bring your own food to save some money at the water park and then bed comfort was very nice.

Reviewed on Aug 10, 2025

Bluegreen Christmas Mountain Village, an Ascend Resort

Bluegreen Christmas Mountain Village, an Ascend Resort

3 out of 5
per person
Sep 25 - Sep 29
found 12 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Madison (MSN)
8.2/10 Very Good! (116 reviews)
We had stayed in this property before, and again this trip did not disappoint!

Reviewed on Jul 22, 2025

The Wisconsin Hotel & Conference Center

The Wisconsin Hotel & Conference Center

2.5 out of 5
per person
Sep 25 - Sep 29
found 12 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Madison (MSN)
8.8/10 Excellent! (24 reviews)
Great stay and great price. The pool and restaurant were closed but we didn't mind. We thoroughly enjoyed the new spacious rooms!

Reviewed on Aug 11, 2025

DoubleTree by Hilton Madison Downtown

DoubleTree by Hilton Madison Downtown

4 out of 5
Downtown Madison
Save 100% on your flight
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Madison (MSN)
9.6/10 Exceptional! (1,005 reviews)
We are here for UW Madison SOAR program. It’s walking distance to almost every where you need to be on campus. If you don’t want to walk, the hotel shuttle can take you there, just ask for it at the front desk. The beds are comfortable and everything works out great for us.

Reviewed on Aug 8, 2025

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Helena Hotel Deals

Cedarberry Inn

Cedarberry Inn

2.5 out of 5
855 Phillips Blvd, Sauk City, WI
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $118 total per night from Aug 14 to Aug 15
$118 total
Aug 14 - Aug 15
Total includes taxes and fees
9/10 Wonderful! (542 reviews)
"Great non-chain option!"

Reviewed on Aug 9, 2025

Cedarberry Inn
Don Q Inn

Don Q Inn

2.5 out of 5
3658 State Road 23, Dodgeville, WI
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $80 total per night from Sep 11 to Sep 12
$80 total
Sep 11 - Sep 12
Total includes taxes and fees
8/10 Very Good! (1,001 reviews)
"The rooms were clean and the lounge was unique with barber chairs. The plane outside looked neat too."

Reviewed on Jul 13, 2025

Don Q Inn
Deer Valley Lodge & Golf

Deer Valley Lodge & Golf

2.5 out of 5
401 West Industrial Drive, Barneveld, WI
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $115 total per night from Aug 14 to Aug 15
$115 total
Aug 14 - Aug 15
Total includes taxes and fees
8.8/10 Excellent! (639 reviews)
"Decor was fabulous."

Reviewed on Aug 8, 2025

Deer Valley Lodge & Golf
See all 85 properties in Helena
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 Helena vacation package cost?
You can grab a vacation package to this top destination from $491 on Expedia. But how much your vacation to Helena costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Helena?
December, January and February are the best times to look for cheap Helena vacation packages. Traveling in less busy months means you can typically find reduced prices on hotels and flights.
How many days is enough for Helena?
Typically, a handful of days is enough to check out the top attractions during your Helena vacation. But if you want to have more time to chill out or go on day trips, think about extending your itinerary.
How to find the best Helena package deals?
Landing a cheap Helena package deal is easy with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add a couple of filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Helena package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Helena vacation as a package?
You can enjoy significant savings on your next Helena escape by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to view the best hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Helena?
If you've got your Helena vacation dates locked in, book as early as you can to grab some fantastic deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for setting off on a whim.
Does Expedia offer Book Now, Pay Later Helena vacation packages?
If you're like us, you love jet-setting around the world but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Helena vacation over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.