Southwest Wisconsin Romantic Holidays

Book a Romantic Hotel + Flight or Car together to unlock savings

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    Find the right fit
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How to find a romantic Southwest Wisconsin holiday

How can I find the best Southwest Wisconsin vacation packages for couples?

Use our easy-to-use holiday search tools to plan your most-romantic getaway to Southwest Wisconsin. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino.

Can I book cheap Southwest Wisconsin romantic holidays for two?

Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Southwest Wisconsin that start from . Prices and availability are subject to change. Additional terms may apply.

What should I think about when booking a Southwest Wisconsin romantic getaway?

The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure.

What should I look for in a luxury romantic holiday to Southwest Wisconsin?

Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service.

Can I book a romantic hot-tub holiday in Southwest Wisconsin?

What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter.

How can I find romantic holidays for couples in Southwest Wisconsin that are all inclusive?

Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available.

Can I book a romantic trip to Southwest Wisconsin with free cancellation and/or flexible dates?

Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print.

Why should I book my Southwest Wisconsin romantic holiday with Expedia?

At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing.

Top Romantic Southwest Wisconsin Hotels

Ho-Chunk Casino Hotel - Wisconsin Dells
Ho-Chunk Casino Hotel - Wisconsin Dells
4 out of 5
S3214 County Road BD, Baraboo, WI
  • 1 hour drive from University of Wisconsin-Madison
Stay at this 4-star business-friendly hotel in Baraboo. Enjoy free Wi-Fi, free parking and a casino. Popular attractions Kalahari Indoor Waterpark and Noah's ...
Girls trip
"It was a great stay, i will totally come back. Fun times!"

Reviewed on 15 Aug 2022

Ho-Chunk Casino Hotel - Wisconsin Dells
Caribbean Club Resort
Caribbean Club Resort
3 out of 5
1093 Canyon Road, Wisconsin Dells, WI
  • 2 hours drive from University of Wisconsin-Madison
Stay at this 3-star beach condo in Wisconsin Dells. Enjoy an outdoor pool, a private beach and a sauna. Our guests praise the pool and the property condition ...
8/10 Very Good! (346 reviews)

Couples like: Hot tub, on the beach, fireplace

Travellers say...
"The view by Lake Delton was very peaceful. The room is nice. Fully st"

Reviewed on 31 May 2025

Caribbean Club Resort
Great Wolf Lodge Wisconsin Dells
Great Wolf Lodge Wisconsin Dells
3.5 out of 5
1400 Great Wolf Dr, Baraboo, WI
  • 2 hours drive from University of Wisconsin-Madison
Stay at this 3.5-star family-friendly resort in Baraboo. Enjoy 6 indoor pools, 3 restaurants and 2 hot tubs. Our guests praise the helpful staff in their reviews. ...
8.2/10 Very Good! (1,004 reviews)
"My son slept in a soaking wet bed with chlorine. There was construction and there was no balcony excess. The check I I had to pay $19 for parking. Was not expecting"

Reviewed on 3 Jul 2025

Great Wolf Lodge Wisconsin Dells
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.

More holidays you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.