Top Romantic vacation packages in Southeast Wisconsin

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

Saint Kate - The Arts Hotel

Downtown Milwaukee

$559

per person

Aug 11 - Aug 13

found 11 hours ago

Roundtrip non-stop flight included

Omaha (OMA) to Milwaukee (MKE)

9.8/10 Exceptional! (2,645 reviews)

The best hotel in Milwaukee!

Reviewed on Jul 7, 2026

The Pfister Hotel

Downtown Milwaukee

Save 100% on your flight

$1,466

per person

Aug 6 - Aug 9

found 24 hours ago

Roundtrip non-stop flight included

Mesa (AZA) to Milwaukee (MKE)

9.6/10 Exceptional! (2,139 reviews)

Excellent stay, nice staff. Nice lounge on the 23rd floor with great drinks and amazing view. The bar lounge on the first floor was also amazing.

Reviewed on Jul 6, 2026

The Delafield Hotel

$1,058

per person

Sep 13 - Sep 17

found 9 hours ago

Roundtrip non-stop flight included

Ontario Intl. Airport (ONT) to Milwaukee (MKE)

9.6/10 Exceptional! (484 reviews)

Lodge Geneva National

$569

per person

Sep 13 - Sep 16

found 5 hours ago

Roundtrip flight included

New York (NYC) to Chicago (ORD)

8.8/10 Excellent! (1,380 reviews)

This is a nice hotel, and this was our third visit to the hotel. However, we planned the stay based solely on using the outdoor pool, and didn't realize the hotel sells passes to people who are not staying at the resort. The pool was crowded. There was only one bartender to make drinks for everyone but there were probably 8 servers who were standing around waiting for drinks to be made. It ruined the vibe we were hoping for.

Reviewed on Jul 6, 2026

Grand Geneva Resort & Spa

$1,440

per person

Aug 17 - Aug 21

found 1 day ago

Roundtrip flight included

Seattle (SEA) to Chicago (ORD)

8.8/10 Excellent! (1,001 reviews)

We had unusual experience this trip. We were anticipating a fun 4th of July celebration ( actually celebrating on the 3rd. ) While swimming at the pool the weather began to change and a severe storm was heading our way. Staff began warning us. Everyone began to take cover at the closest entrance. As we all huddled inside the building, a tornado alert went off on everyone’s phones. The staff guided us to the lower level. They were so professional. While waiting out the storm( about 30-40 minutes) the staff began passing out towels( we were all wet from the pool) water bottles and snack bars. They really took care of us. It was a terrible storm and after about 30 minutes the power went out. When the storm passed, we began to assess the damage. Trees and huge branches were down all over the property. Power was out for about 4-5 hours. We were just so impressed by the staff’s attention to all of us. The next morning, we received a note under our hotel room’s door saying that, as a thank you, everyone was welcome to a free Happy Hour poolside, with free beer and wine and appetizers. This was Icing on the cake and definitely not expected. Although our stay was not what we had hoped due to the storm and power outage, the staff and managers did such a great job of keeping people safe and calm, it will definitely be one of the most memorable. Thank you Grand Geneva, for your attentiveness to the situation and taking care of your patrons. We really appreciated it!

Reviewed on Jul 4, 2026

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3 Night Romantic vacations in Southeast Wisconsin

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

Saint Kate - The Arts Hotel

Downtown Milwaukee

$577

per person

Sep 11 - Sep 14

found 1 day ago

Roundtrip non-stop flight included

Akron (CAK) to Milwaukee (MKE)

9.8/10 Exceptional! (2,645 reviews)

The best hotel in Milwaukee!

Reviewed on Jul 7, 2026

The Pfister Hotel

Downtown Milwaukee

Save 100% on your flight

$780

per person

Sep 11 - Sep 14

found 1 day ago

Roundtrip non-stop flight included

Akron (CAK) to Milwaukee (MKE)

9.6/10 Exceptional! (2,139 reviews)

Excellent stay, nice staff. Nice lounge on the 23rd floor with great drinks and amazing view. The bar lounge on the first floor was also amazing.

Reviewed on Jul 6, 2026

The Iron Horse Hotel

Fifth Ward

$604

per person

Sep 11 - Sep 14

found 1 day ago

Roundtrip non-stop flight included

Akron (CAK) to Milwaukee (MKE)

9.2/10 Wonderful! (1,192 reviews)

Iron Horse is an excellent property! The lobby and lounging areas are so well decorated and inviting, you want to spend as much time there as your room. But the rooms are huge with fabulous decor and amenities so you might not want to leave. We also had dinner at their restaurant - The Yards. We sat in the outdoor area which was spacious with an outdoor bar and various levels and areas to dine. The food was excellent. We only stayed for one night as we were passing through but we hope to get back to Milwaukee some time so we can enjoy a longer stay.

Reviewed on Jul 6, 2026

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4 Night Romantic vacations in Southeast Wisconsin

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

Timber Ridge Lodge and Waterpark

$809

per person

Aug 17 - Aug 21

found 1 day ago

Roundtrip flight included

Seattle (SEA) to Chicago (ORD)

8.6/10 Excellent! (3,294 reviews)

Room hasn’t been updated in years. Carpets, bathrooms, and kitchen are dingy and old. Loft AC not functioning. The water park is great but rooms are in need of major renovations.

Reviewed on Jul 6, 2026

The Pfister Hotel

Downtown Milwaukee

Save 100% on your flight

$1,310

per person

Aug 6 - Aug 10

found 13 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Milwaukee (MKE)

9.6/10 Exceptional! (2,139 reviews)

Excellent stay, nice staff. Nice lounge on the 23rd floor with great drinks and amazing view. The bar lounge on the first floor was also amazing.

Reviewed on Jul 6, 2026

The Delafield Hotel

$1,058

per person

Sep 13 - Sep 17

found 9 hours ago

Roundtrip non-stop flight included

Ontario Intl. Airport (ONT) to Milwaukee (MKE)

9.6/10 Exceptional! (484 reviews)

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

To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.

How can I find cheap Southeast Wisconsin romantic packages for two?

For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering.

How can I plan a great romantic trip to Southeast Wisconsin?

Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.

How much is a trip for two to Southeast Wisconsin?

Put a price on love with stunning deals for duos starting at just $559. Prices and availability are subject to change. Additional terms may apply.

Can I book Southeast Wisconsin spa packages for couples?

Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.

How can I book romantic weekend getaway packages in Southeast Wisconsin?

To book a loved-up break in Southeast Wisconsin, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).

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

The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.

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

If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?

Top Romantic Southeast Wisconsin Hotels

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI

7 min drive from American Family Field

You and your special someone are sure to love the

9.6/10 Exceptional! (2,156 reviews)

Couples like: full-service spa, couples spa treatments, bar

Travelers say...

"Excellent stay, nice staff. Nice lounge on the 23rd floor with great drinks and amazing view. The bar lounge on the first floor was also amazing."

Reviewed on Jul 6, 2026

Lake Lawn Resort

2400 E Geneva St Delavan WI

1 hour drive from American Family Field

A spa, a garden, and a hot tub await couples visiting this romantic resort. The property also offers poolside dining, a lobby fireplace, and a lakeside ...

9.2/10 Wonderful! (1,010 reviews)

Couples like: full-service spa, couples spa treatments, poolside dining, hot tub

Travelers say...

"Everything about this resort is wonderful. Will keep returning!"

Reviewed on Jul 6, 2026

Hotel Metro, Autograph Collection

411 E Mason St Milwaukee WI

7 min drive from American Family Field

Love is in the air at this boutique hotel, featuring a garden, a lobby fireplace, and Egyptian cotton sheets. Couples will love the rooftop terrace and Art Deco ...

8.2/10 Very Good! (1,001 reviews)

"The hotel was only a 1 mile walk from Summerfest, which was wonderful. We were allowed to check in 3 hours early, making our day even smoother. Valet was quick and simple. The staff was kind and the accommodations were impressive. Will return here for sure."

Reviewed on Jul 5, 2026

See all 2,461 properties in Southeast Wisconsin

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.