
Southeast Wisconsin Pet-friendly Vacations
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Flight and Pet-friendly hotel deals in Southeast Wisconsin
Price found within the past 48 hours. Click for updated prices.

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham
Avenues West
Price was CA $1,075, price is now CA $1,049 per person
CA $1,049
per person
Jun 15 - Jun 17
found 22 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9/10 Wonderful! (1,329 reviews)
Room was great. Bed was very comfortable and great view
Reviewed on Apr 27, 2026

The Pfister Hotel
Downtown Milwaukee
Price was CA $2,130, price is now CA $1,587 per person
CA $1,587
per person
Jun 18 - Jun 21
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Milwaukee (MKE)
9.6/10 Exceptional! (2,083 reviews)
Beautiful and elegant. Great food. Fun rooftop bar. Wonderful spa experience, both pedicure and massage. I’ll definitely be back. We’re already planning our next visit here.
Reviewed on Apr 22, 2026

The Iron Horse Hotel
Fifth Ward
Price was CA $1,753, price is now CA $1,468 per person
CA $1,468
per person
Jun 18 - Jun 21
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Milwaukee (MKE)
9.2/10 Wonderful! (1,067 reviews)
Staff was very nice and helpful. They need more snack options to quickly buy.
Reviewed on Apr 24, 2026

Kimpton Journeyman Hotel by IHG
Downtown Milwaukee
Price was CA $1,939, price is now CA $1,755 per person
CA $1,755
per person
Jun 18 - Jun 21
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Milwaukee (MKE)
9.4/10 Exceptional! (979 reviews)
Great place and stay. Walking distance to so much fun places.
Reviewed on Apr 3, 2026
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See all available trips from Columbus to Southeast Wisconsin
View all trips3 Night Pet-friendly holidays in Southeast Wisconsin
Price found within the past 48 hours. Click for updated prices.

The Iron Horse Hotel
Fifth Ward
Price was CA $1,753, price is now CA $1,468 per person
CA $1,468
per person
Jun 18 - Jun 21
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Milwaukee (MKE)
9.2/10 Wonderful! (1,067 reviews)
Staff was very nice and helpful. They need more snack options to quickly buy.
Reviewed on Apr 24, 2026

The Pfister Hotel
Downtown Milwaukee
Price was CA $2,130, price is now CA $1,587 per person
CA $1,587
per person
Jun 18 - Jun 21
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Milwaukee (MKE)
9.6/10 Exceptional! (2,083 reviews)
Beautiful and elegant. Great food. Fun rooftop bar. Wonderful spa experience, both pedicure and massage. I’ll definitely be back. We’re already planning our next visit here.
Reviewed on Apr 22, 2026

Kimpton Journeyman Hotel by IHG
Downtown Milwaukee
Price was CA $1,939, price is now CA $1,755 per person
CA $1,755
per person
Jun 18 - Jun 21
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Milwaukee (MKE)
9.4/10 Exceptional! (979 reviews)
Great place and stay. Walking distance to so much fun places.
Reviewed on Apr 3, 2026
Don't see what you're looking for?
See all available trips from Columbus to Southeast Wisconsin
View all tripsPet-friendly Hotels in Southeast Wisconsin

Drury Plaza Hotel Milwaukee Downtown
700 N. Water Street Milwaukee WI
Book a stay at this business-friendly hotel in Milwaukee. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
9.6/10 Exceptional! (2,186 reviews)
Clean. Quiet. Check in was quick. Parking was ready. Drinks in the bar were great. The staff is awesome. Have stayed here several times and stay again!
Reviewed on Apr 27, 2026

The Iron Horse Hotel
500 W Florida Street Milwaukee WI
Book a stay at this boutique hotel in Milwaukee. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,076 reviews)
My room was not clean when I arrived at 10:30pm. The receptionist and bar staff were amazing, but because the hotel was sold out we were sent to another hotel. That hotel room was much smaller, smelled like sewage, and had maintenance issues. The staff were amazing, but if management thinks that ...
Reviewed on Apr 25, 2026

The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9.6/10 Exceptional! (2,080 reviews)
The pool
Reviewed on Apr 25, 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.
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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.







