Helena Vacation Packages

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Top Helena Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Comfort Suites Madison West - Middleton

Comfort Suites Madison West - Middleton

2.5 out of 5
per person
Sep 3 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
8/10 Very Good! (353 reviews)
We went for the pool, but a child pooped in it, so pool was shut down from 11am Saturday until we left 11am Sunday. Online, it says all they had to do was remove feces and shock water with chemicals and recirculate clean water, 2 hours. Why did nothing get cleaned in over 24 hours?

Reviewed on Jul. 11, 2025

DoubleTree by Hilton Madison Downtown

DoubleTree by Hilton Madison Downtown

4 out of 5
Downtown Madison
per person
Sep 3 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
9.6/10 Exceptional! (1,005 reviews)
Very clean, staff was friendly

Reviewed on Jul. 8, 2025

Christmas Mountain Campground

Christmas Mountain Campground

3 out of 5
per person
Sep 3 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
9/10 Wonderful! (52 reviews)
We did not have any issues during our stay. There are so many activities to do around the property. The only thing we didn’t love was there were no clear instructions regarding check out as in if we had to check out at the office, where to leave garbage or used towels etc. Everything else was fantastic, a quiet family friendly resort!

Reviewed on Jul. 14, 2025

Cambria Hotel Madison East

Cambria Hotel Madison East

3 out of 5
per person
Sep 3 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
8.8/10 Excellent! (1,006 reviews)
Room was very clean. I wish you would have had a shuttle that could have driven us to downtown but we managed.

Reviewed on Jul. 7, 2025

AmericInn by Wyndham Madison South

AmericInn by Wyndham Madison South

2.5 out of 5
Monona
per person
Sep 3 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
9/10 Wonderful! (1,006 reviews)
I booked a handicap accessible room and got it. It was very nice for my sister in a wheelchair. The pool area was nice. Room was clean.

Reviewed on Jul. 16, 2025

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
The price is CA $145 per night from Jul 20 to Jul 21
CA $145
CA $162 total
Jul 20 - Jul 21
includes taxes & fees
9/10 Wonderful! (513 reviews)
"Clean room pull out couch… uncomfortable!"

Reviewed on Jul. 15, 2025

Cedarberry Inn
AmericInn by Wyndham Dodgeville

AmericInn by Wyndham Dodgeville

2.5 out of 5
3637 State Road 23, Dodgeville, WI
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Aug 10 to Aug 11
CA $144
CA $164 total
Aug 10 - Aug 11
includes taxes & fees
8.2/10 Very Good! (511 reviews)
"The rooms were clean. Price was very good. The breakfast was good."

Reviewed on Jul. 14, 2025

AmericInn by Wyndham Dodgeville
Don Q Inn

Don Q Inn

2.5 out of 5
3658 State Road 23, Dodgeville, WI
Fully refundableReserve now, pay when you stay
The price is CA $98 per night from Jul 20 to Jul 21
CA $98
CA $112 total
Jul 20 - Jul 21
includes taxes & fees
8/10 Very Good! (1,000 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
See all 84 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.

All Inclusive Vacations

All Inclusive Vacations

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Frequently asked questions

How much does a Helena vacation package cost?
Offering great value package deals from CA $1,219 on Expedia, you'll be thrilled with how little a vacation to Helena costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Helena?
January, February and April are the best times to search for cheap Helena vacation packages. Choosing to travel in quieter periods means you'll typically find reduced prices on accommodations and flights.
How many days is enough for Helena?
With a well-organized travel plan, you can easily hit the top Helena sights in a few days. But if you prefer to discover lesser-known spots or take day trips, think about booking your Helena vacation for longer.
How to find the best Helena package deals?
Finding a cheap Helena package deal is a breeze with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget range, add a few filters and see 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 affordable Helena package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Helena vacation as a package?
You can enjoy significant savings on your next Helena retreat by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to see the best flight and hotel prices. Bundle everything into a neat package and you can save 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're considering a spontaneous Helena getaway, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Helena?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Helena.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and meals to activities and airfares. Your accommodations will probably be the largest expense during your trip to Helena.
  3. Work out your trip length: Consider how much time you'd like to spend discovering Helena. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored Helena vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.