Southeast Wisconsin Pet-friendly Vacations

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Top Pet-friendly vacation packages in Southeast Wisconsin

Price found within the past 48 hours. Click for updated prices.
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Marquette
$561
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Milwaukee (MKE)
9/10 Wonderful! (1,399 reviews)
Charming vintage hotel right on the edge of downtown Milwaukee. The staff was exceptional and helpful all around. Lots of fun touches from the past around the hotel.

Reviewed on Oct 23, 2026

The Pfister Hotel

The Pfister Hotel

Downtown Milwaukee
Save 100% on your flight
$861
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Milwaukee (MKE)
9.6/10 Exceptional! (2,299 reviews)
I was surprised that the Pfister does not have any courtesy shuttle at all. I thought it was a full service hotel. I was in Milwaukee attending a conference at a center nearly a mile away. Normally, I don't mind walking, but one day it was pouring down rain sideways, and I got soaked to the skin, despite wearing a rain coat. I ate breakfast in the hotel cafe and was shocked that cafe staff allowed a family in with a huge dog, that was wearing an obviously fake "medical alert dog" vest on. The family members were constantly petting the dog and feeding it from the table. A real medical alert dog is trained to stay on the floor, and would not be getting petted or fed from the table. This dog had it's snout on the table. Another party was seated at the same table after the dog owners left. No deep cleaning of the table was done. Having seen this, I would not eat at the cafe again.

Reviewed on Oct 23, 2026

The Iron Horse Hotel

The Iron Horse Hotel

Fifth Ward
$881
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Milwaukee (MKE)
9.2/10 Wonderful! (1,378 reviews)
Kimpton Journeyman Hotel by IHG

Kimpton Journeyman Hotel by IHG

Downtown Milwaukee
$648
per person
Dec 30 - Jan 2
found 13 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to Milwaukee (MKE)
9.4/10 Exceptional! (1,000 reviews)
Hilton Milwaukee

Hilton Milwaukee

Westown
$605
per person
Jan 1 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Milwaukee (MKE)
8.6/10 Excellent! (1,214 reviews)
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3 Night Pet-friendly vacations in Southeast Wisconsin

Price found within the past 48 hours. Click for updated prices.
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Marquette
$543
per person
Dec 30 - Jan 2
found 13 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to Milwaukee (MKE)
9/10 Wonderful! (1,399 reviews)
Charming vintage hotel right on the edge of downtown Milwaukee. The staff was exceptional and helpful all around. Lots of fun touches from the past around the hotel.

Reviewed on Oct 23, 2026

The Pfister Hotel

The Pfister Hotel

Downtown Milwaukee
$633
per person
Dec 30 - Jan 2
found 13 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to Milwaukee (MKE)
9.6/10 Exceptional! (2,299 reviews)
I was surprised that the Pfister does not have any courtesy shuttle at all. I thought it was a full service hotel. I was in Milwaukee attending a conference at a center nearly a mile away. Normally, I don't mind walking, but one day it was pouring down rain sideways, and I got soaked to the skin, despite wearing a rain coat. I ate breakfast in the hotel cafe and was shocked that cafe staff allowed a family in with a huge dog, that was wearing an obviously fake "medical alert dog" vest on. The family members were constantly petting the dog and feeding it from the table. A real medical alert dog is trained to stay on the floor, and would not be getting petted or fed from the table. This dog had it's snout on the table. Another party was seated at the same table after the dog owners left. No deep cleaning of the table was done. Having seen this, I would not eat at the cafe again.

Reviewed on Oct 23, 2026

The Iron Horse Hotel

The Iron Horse Hotel

Fifth Ward
$603
per person
Dec 30 - Jan 2
found 13 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to Milwaukee (MKE)
9.2/10 Wonderful! (1,378 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Southeast Wisconsin
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4 Night Pet-friendly vacations in Southeast Wisconsin

Price found within the past 48 hours. Click for updated prices.
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Marquette
$451
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Milwaukee (MKE)
9/10 Wonderful! (1,399 reviews)
Charming vintage hotel right on the edge of downtown Milwaukee. The staff was exceptional and helpful all around. Lots of fun touches from the past around the hotel.

Reviewed on Oct 23, 2026

The Iron Horse Hotel

The Iron Horse Hotel

Fifth Ward
$685
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Milwaukee (MKE)
9.2/10 Wonderful! (1,378 reviews)
The Pfister Hotel

The Pfister Hotel

Downtown Milwaukee
$776
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Milwaukee (MKE)
9.6/10 Exceptional! (2,299 reviews)
I was surprised that the Pfister does not have any courtesy shuttle at all. I thought it was a full service hotel. I was in Milwaukee attending a conference at a center nearly a mile away. Normally, I don't mind walking, but one day it was pouring down rain sideways, and I got soaked to the skin, despite wearing a rain coat. I ate breakfast in the hotel cafe and was shocked that cafe staff allowed a family in with a huge dog, that was wearing an obviously fake "medical alert dog" vest on. The family members were constantly petting the dog and feeding it from the table. A real medical alert dog is trained to stay on the floor, and would not be getting petted or fed from the table. This dog had it's snout on the table. Another party was seated at the same table after the dog owners left. No deep cleaning of the table was done. Having seen this, I would not eat at the cafe again.

Reviewed on Oct 23, 2026

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Top Pet-friendly Southeast Wisconsin Hotels

Grand Geneva Resort & Spa

Grand Geneva Resort & Spa

7036 Grand Geneva Wy Lake Geneva WI
  • 1 hour drive from American Family Field
This family-friendly, lakefront resort welcomes dogs (fees apply) with pet-friendly perks such as food and water bowls. While you're here, explore nearby hiking ...
Grand Geneva Resort & Spa
The Pfister Hotel

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI
  • 7 min drive from American Family Field
Dogs and cats are welcome (fees apply) at this luxury hotel, so bring your four-legged friend along for a pet-friendly, city-center getaway. For a stroll, try ...
9.6/10 Exceptional! (2,296 reviews)
"I was surprised that the Pfister does not have any courtesy shuttle at all. I thought it was a full service hotel. I was in Milwaukee attending a conference at a center nearly a mile away. Normally, I don't mind walking, but one day it was pouring down rain sideways, and I got soaked to the skin, ..."

Reviewed on Oct 23, 2026

The Pfister Hotel
Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

333 W Kilbourn Ave Milwaukee WI
  • 6 min drive from American Family Field
Hiking and biking trails are ready for you to explore near this city-center hotel, where dogs can stay for an additional fee.
8.6/10 Excellent! (1,560 reviews)
"Breakfast was not good, but everything else was"

Reviewed on Oct 22, 2026

Hyatt Regency Milwaukee
See all 2,437 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.

More vacations you might like

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