Search Deals onSheboygan Vacation Packages
Sheboygan Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
County Clare Irish Hotel & Pub
Price was $555, price is now $468 per person
$468
per person
Jan 29 - Feb 1
found 9 hours ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
Stay at this hotel in Milwaukee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Fiserv Forum and Harley-Davidson Museum are located nearby.
The Pfister Hotel
Price was $1,166, price is now $898 per person
$898
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Milwaukee (MKE)
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 in our reviews. Popular attractions Fiserv Forum and Harley-Davidson Museum are located nearby.
Staff and amenities are always the highlight of staying. A favorite of ours whether it’s for an overnight or weekend away. Truly unique
Reviewed on Nov 3, 2026
The Iron Horse Hotel
Price was $894, price is now $692 per person
$692
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Milwaukee (MKE)
Book a stay at this boutique hotel in Milwaukee. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Harley-Davidson Museum and Potawatomi Bingo Casino are located nearby.
Kinn Guesthouse Bay View
Price was $748, price is now $619 per person
$619
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, free parking, and a fireplace in the lobby. Our guests praise the clean rooms in our reviews. Popular attractions Harley-Davidson Museum and Potawatomi Bingo Casino are located nearby.
Great space in the room.
Good setting.
Ventilation system was loud.
Be prepared for stairs.
Reviewed on Nov 5, 2026
Kimpton Journeyman Hotel by IHG
Price was $608, price is now $507 per person
$507
per person
Jan 29 - Feb 1
found 9 hours ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, 2 bars/lounges, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Harley-Davidson Museum and Fiserv Forum are located nearby.
Hyatt Regency Milwaukee
Price was $576, price is now $506 per person
$506
per person
Jan 29 - Feb 1
found 9 hours ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
Book a stay at this business-friendly hotel in Milwaukee. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fiserv Forum and Harley-Davidson Museum are located nearby.
Great stay.
Reviewed on Nov 6, 2026
Marriott Milwaukee Downtown
Price was $601, price is now $528 per person
$528
per person
Jan 29 - Feb 1
found 9 hours ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
Book a stay at this business-friendly hotel in Milwaukee. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fiserv Forum and Harley-Davidson Museum are located nearby.
Sheboygan Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Sheboygan Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Mon, Nov 23 - Tue, Dec 1
CLE
Hopkins Intl.
MKE
General Mitchell Intl.
$265 Roundtrip, found 6 days ago
$265
Roundtrip
found 6 days ago
Sun, Nov 22 - Wed, Nov 25
CLE
Hopkins Intl.
MKE
General Mitchell Intl.
$290 Roundtrip, found 6 days ago
$290
Roundtrip
found 6 days ago
Wed, Nov 25 - Sat, Nov 28
CLE
Hopkins Intl.
MKE
General Mitchell Intl.
$337 Roundtrip, found 6 days ago
$337
Roundtrip
found 6 days ago
Wed, Nov 25 - Sat, Nov 28
CLE
Hopkins Intl.
MKE
General Mitchell Intl.
$337 Roundtrip, found 6 days ago
$337
Roundtrip
found 6 days ago
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