Arena Vacations from $380
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The Latest Arena Vacation Packages
- Club Wyndham Tamarack
Oct 30 - Nov 1Club Wyndham Tamarack + Flight
Wisconsin Dells2 nights3.5 star property9.4/10 - Exceptional (24 reviews)"The room was spotless and it was nice to relax with the fireplace. Also enjoyed saving money by buying and cooking our own meals. "Reviewed May 12, 2026Roundtrip • Chicago (CHI) - Madison (MSN)ORD - MSN • Nonstop MSN - ORD • Nonstop$431$380found 1 day agoper traveler - Dellshire Resort
Sep 30 - Oct 4Dellshire Resort + Flight
Wisconsin Dells4 nights3.5 star property9.0/10 - Wonderful (268 reviews)Roundtrip • Chicago (CHI) - Madison (MSN)ORD - MSN • Nonstop MSN - ORD • Nonstop$678$575found 1 hour agoper traveler - Days Inn & Suites by Wyndham Madison
Sep 23 - Sep 27Days Inn & Suites by Wyndham Madison + Flight
Madison4 nights2.0 star property8.6/10 - Excellent (1,010 reviews)"Staff was very helpful. We came an hour before check in because of bad weather and they made quick efforts to finish cleaning our room. Breakfast was also better than expected. Loved the fresh biscuits and gravy. Thanks. 🙏"Reviewed August 4, 2026Roundtrip • Denver (DEN) - Madison (MSN)DEN - MSN • 1 stop MSN - DEN • Nonstop$614$531found 4 hours agoper traveler - Days Inn by Wyndham Madison NE/Windsor
Sep 23 - Sep 27Days Inn by Wyndham Madison NE/Windsor + Flight
Windsor4 nights2.0 star property7.2/10 - Good (1,004 reviews)"I reserved a room for my 25 year old grandson and girl friend for four days starting July 30, 2026. On check-in they were given a room that was not clean, They complained and were given another room that also had a bad odor and seemed moldy, so they cancelled without occupying. I was charged one day of rent and Expedia refunded the remainder. I tried multiple times to contact Days Inn and Expedia to protest the charge but was unable to get through the maze of online virtual support and..."Reviewed August 4, 2026Roundtrip • Denver (DEN) - Madison (MSN)DEN - MSN • 1 stop MSN - DEN • Nonstop$513$451found 4 hours agoper traveler - AmericInn by Wyndham Madison South
Sep 23 - Sep 27AmericInn by Wyndham Madison South + Flight
Monona4 nights3.0 star property9.0/10 - Wonderful (1,006 reviews)"Quiet hotel with pool and whirlpool."Reviewed August 4, 2026Roundtrip • Denver (DEN) - Madison (MSN)DEN - MSN • 1 stop MSN - DEN • Nonstop$693$609found 4 hours agoper traveler
Arena Hotel Deals
"Fabulous hot breakfast. Brand new showers in all units"
Homewood Suites by Hilton Madison West
Homewood Suites by Hilton Madison West"Just a really nice place. Will be back"
Holiday Inn Express & Suites Madison West - Middleton by IHG
Holiday Inn Express & Suites Madison West - Middleton by IHG
Residence Inn by Marriott Madison West/Middleton
Residence Inn by Marriott Madison West/Middleton"The staff at this property is the best"
Courtyard by Marriott Madison West Middleton
Courtyard by Marriott Madison West Middleton"The bistro pricing posted on signage did not match the pricing in the menus. I was informed the menus needed to be updated but the lower pricing was not honoured."
Fairfield Inn & Suites by Marriott Madison West/Middleton
Fairfield Inn & Suites by Marriott Madison West/Middleton
TownePlace Suites by Marriott Madison West/Middleton
TownePlace Suites by Marriott Madison West/Middleton"loved it!"
Frequently Asked Questions
How much does an Arena vacation package cost?
You can snap up a vacation package to this destination from $380 on Expedia. But how much your vacation to Arena costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Arena?
You can usually find lower prices and greater availability in December, January and February. Check out our cheap Arena vacation packages and you could land some great off-season discounts.
How many days is enough for Arena?
With a well-organized itinerary, you can easily visit the main Arena attractions in a few days. But if you prefer to discover hidden gems or take day trips, think about booking your Arena vacation for longer.
How to find the best Arena package deals?
Use Expedia's handy filters to help you find some fabulous Arena package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or browse for Arena package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book an Arena vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Arena vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Arena?
Enjoy incredible discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Arena break.
Does Expedia offer Book Now, Pay Later Arena vacation packages?
If you're like us, you love jet-setting around the world but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Arena break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.