Cross Plains Vacations from $517

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Your Cross Plains Vacation

Put together a custom vacation package to Cross Plains and prepare to experience this exciting city how you want. Think about spending some time in the neighborhood of Shorewood Hills, which is good for golfing and lots more. When it's time to venture out and explore, be sure to put Pleasant View Golf Course and Cross Plains State Park on the itinerary for your trip to Cross Plains. Don't delay visiting this destination any longer. Your perfect Cross Plains vacation is a few quick clicks away with Expedia.

The Latest Cross Plains vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Ruby Marie

Hotel Ruby Marie

Downtown Madison
$517
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip flight included
Denver (DEN) to Madison (MSN)
9.4/10 Exceptional! (1,003 reviews)
Club Wyndham Glacier Canyon

Club Wyndham Glacier Canyon

$537
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Denver (DEN) to Madison (MSN)
9/10 Wonderful! (426 reviews)
My husband and I stayed with Club Wyndham for the first time at the Wilderness Glacier Canyon Lodge. Our four night stay was nothing but pure bliss, and we definitely plan on coming back! After check-in we were told about some of the benefits Wyndham timeshares had to offer and were asked if we would like to attend their tour, but we were not interested at the time to which they had no problem with and told us to enjoy our stay! The Wilderness resort brings back much nostalgia because I used to visit there all the time with my family as a child. Now, my husband and I want to continue the tradition with our family. This place has everything the whole family could want on a vacation. From the waterparks to the arcades to food, they have it all. We have already made so many great memories there, and we highly recommend going! Just remember they do get very busy during peak season, so if you’re looking for a more laid back version of the Wilderness, we recommend going during their off-season! Also, be sure to check out the downtown (our favorite restaurant is the Dell Bar) as well as Devil’s Lake State Park!

Reviewed on Jun 3, 2026

The Edgewater

The Edgewater

Downtown Madison
$788
per person
Sep 24 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Madison (MSN)
9.2/10 Wonderful! (1,007 reviews)
Fairfield by Marriott Inn & Suites Madison South

Fairfield by Marriott Inn & Suites Madison South

$599
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Denver (DEN) to Madison (MSN)
9/10 Wonderful! (189 reviews)
Dellshire Resort

Dellshire Resort

$582
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Madison (MSN)
9/10 Wonderful! (232 reviews)
Beautiful hotel and well maintained and clean. We suggest a clock in the pool area outside and inside.

Reviewed on Aug 10, 2026

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Stay near popular Cross Plains attractions

Cross Plains State Park

You can take time to visit Cross Plains State Park during your travels to Cross Plains.
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Cross Plains Hotel Deals

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
$127 nightly
$146 total
Sep 7 - Sep 8
Total with taxes and fees
The Madison Concourse Hotel and Governor's Club
Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

8102 Excelsior Dr Madison WI
Fully refundableReserve now, pay when you stay
$67 nightly
$78 total
Aug 23 - Aug 24
Total with taxes and fees
8/10 Very Good! (1,423 reviews)
"Overall Great experience for one night. Pool amenities were clean and comfortable. Room was clean and well maintained. Staff was ok and if they can be more committed to there job and understanding it would be helpful."

Reviewed on Aug 10, 2026

Baymont by Wyndham Madison West/Middleton WI West
Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

2424 University Avenue Madison WI
Fully refundableReserve now, pay when you stay
$126 nightly
$146 total
Aug 30 - Aug 31
Total with taxes and fees
9.2/10 Wonderful! (1,023 reviews)
"Things were starting to fall apart in our bathroom, like loose fixtures and missing caulk, etc."

Reviewed on Aug 10, 2026

Best Western Plus InnTowner Madison
See all 498 properties in Cross Plains
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 Cross Plains Vacation Packages

Cross Plains Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Dane County Regional Airport (MSN)
Population
4,000
Top Sights
Cave of The Mounds National Natural Landmark, Wollersheim Winery and Blue Mound State Park

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Frequently asked questions

How much does a Cross Plains vacation package cost?
Offering great value package deals from $517 on Expedia, you'll be surprised at how little a vacation to Cross Plains costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Cross Plains?
If you'd like to snag a cheap Cross Plains vacation package, consider planning a trip in November, December and January. You'll generally find lower rates on hotels and airfares during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Cross Plains?
With a well-organized itinerary, you can easily tick off the top Cross Plains sights in a few days. But if you'd like to explore off the beaten track or go on day trips, consider booking your Cross Plains vacation for longer.
How to find the best Cross Plains package deals?
Landing a cheap Cross Plains package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Cross Plains 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 generally lower.
Is it cheaper to book a Cross Plains vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, flight and hotel 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 have the freedom to create a customized Cross Plains vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Cross Plains?
If you have your Cross Plains travel dates confirmed, book as early as you can to bag some terrific deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for traveling on a whim.
Does Expedia offer Book Now, Pay Later Cross Plains vacation packages?
Your Cross Plains getaway should be an escape from your busy life, not a reason for money worries. So to allow you that extra flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

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