Wisconsin Pet-friendly Vacations
Book a Pet-friendly Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Pet-friendly vacation packages in Wisconsin
Price found within the past 48 hours. Click for updated prices.
The Iron Horse Hotel
Fifth Ward
Price was $1,154, price is now $938 per person
$938
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Milwaukee (MKE)
9.2/10 Wonderful! (1,099 reviews)
Everything here is super neat and exciting. The rooms are sleek and rustic. Will stay again 100% Staff was so friendly and extremely helpful.
Reviewed on May 14, 2026
Graduate by Hilton Madison
Downtown Madison
Price was $2,179, price is now $1,771 per person
$1,771
per person
Jul 18 - Jul 22
found 7 hours ago
Roundtrip non-stop flight included
Omaha (OMA) to Madison (MSN)
9/10 Wonderful! (1,005 reviews)
Room clean and had a vent white noise so it was perfect to go to sleep
Reviewed on Apr 29, 2026
Kimpton Journeyman Hotel by IHG
Downtown Milwaukee
Price was $1,205, price is now $1,079 per person
$1,079
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Milwaukee (MKE)
9.4/10 Exceptional! (982 reviews)
Great place and stay. Walking distance to so much fun places.
Reviewed on Apr 3, 2026
3 Night Pet-friendly vacations in Wisconsin
Price found within the past 48 hours. Click for updated prices.
Graduate by Hilton Madison
Downtown Madison
Price was $873, price is now $702 per person
$702
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Madison (MSN)
9/10 Wonderful! (1,005 reviews)
Room clean and had a vent white noise so it was perfect to go to sleep
Reviewed on Apr 29, 2026
The Iron Horse Hotel
Fifth Ward
Price was $1,154, price is now $938 per person
$938
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Milwaukee (MKE)
9.2/10 Wonderful! (1,099 reviews)
Everything here is super neat and exciting. The rooms are sleek and rustic. Will stay again 100% Staff was so friendly and extremely helpful.
Reviewed on May 14, 2026
Kimpton Journeyman Hotel by IHG
Downtown Milwaukee
Price was $1,205, price is now $1,079 per person
$1,079
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Milwaukee (MKE)
9.4/10 Exceptional! (982 reviews)
Great place and stay. Walking distance to so much fun places.
Reviewed on Apr 3, 2026
4 Night Pet-friendly vacations in Wisconsin
Price found within the past 48 hours. Click for updated prices.
All Star Inn & Suites
Price was $588, price is now $484 per person
$484
per person
Aug 7 - Aug 11
found 18 hours ago
Roundtrip non-stop flight included
St. Louis (STL) to Madison (MSN)
9/10 Wonderful! (739 reviews)
Impeccably clean. Maintained with staff who are always ready to help
Reviewed on Oct 26, 2025
The Iron Horse Hotel
Fifth Ward
Price was $1,337, price is now $1,033 per person
$1,033
per person
Jun 18 - Jun 22
found 21 hours ago
Roundtrip non-stop flight included
Richmond (RIC) to Milwaukee (MKE)
9.2/10 Wonderful! (1,099 reviews)
Everything here is super neat and exciting. The rooms are sleek and rustic. Will stay again 100% Staff was so friendly and extremely helpful.
Reviewed on May 14, 2026
Graduate by Hilton Madison
Downtown Madison
Price was $1,193, price is now $930 per person
$930
per person
Jun 17 - Jun 21
found 5 hours ago
Roundtrip non-stop flight included
St. Louis (STL) to Madison (MSN)
9/10 Wonderful! (1,005 reviews)
Room clean and had a vent white noise so it was perfect to go to sleep
Reviewed on Apr 29, 2026
Top Pet-friendly Wisconsin Hotels
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
$139 nightly
The price is $161 total per night from May 24 to May 25
$161 total
May 24 - May 25
Total with taxes and fees
Don't leave your four-legged friend at home during your city-center excursion. Dogs are welcome (fees apply) at this luxury hotel. For a walk, try Olin ...
9.4/10 Exceptional! (3,732 reviews)
Love it there
Reviewed on May 14, 2026
Drury Plaza Hotel Milwaukee Downtown
700 N. Water Street Milwaukee WI
$111 nightly
The price is $131 total per night from May 25 to May 26
$131 total
May 25 - May 26
Total with taxes and fees
This pet-friendly, city-center hotel welcomes dogs and cats for an additional fee. Nearby Lakeshore State Park is a good place to stretch your legs if you need ...
9.6/10 Exceptional! (2,197 reviews)
.
Reviewed on May 14, 2026
The Iron Horse Hotel
500 W Florida Street Milwaukee WI
$189 nightly
The price is $223 total per night from May 31 to Jun 1
$223 total
May 31 - Jun 1
Total with taxes and fees
This family-friendly, city-center hotel welcomes four-legged friends (fees apply) and offers pet-friendly amenities, like food and water bowls. While you're ...
9.2/10 Wonderful! (1,112 reviews)
Everything here is super neat and exciting. The rooms are sleek and rustic. Will stay again 100% Staff was so friendly and extremely helpful.
Reviewed on May 14, 2026
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.
