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A lighthouse at sunset with a colorful sky and calm water.

Sheboygan
Wisconsin
United States of America
North America
Hotwire.com

Sheboygan Flight + Hotel Packages

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

Abbey Resort and Avani Spa

3.5 out of 5

Price was $817, price is now $676 per person

$676

per person

Oct 14 - Oct 18

found 17 hours ago

Roundtrip flight included

Dallas (DFW) to Milwaukee (MKE)

Book a stay at this beach resort in Fontana. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Geneva Lake and Fontana Beach are located nearby.

Excellent location, very clean. Also, very quiet.

Reviewed on Aug 27, 2026

Saint Kate - The Arts Hotel

4 out of 5

Price was $1,667, price is now $1,185 per person

$1,185

per person

Sep 27 - Oct 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Milwaukee (MKE)

Stay at this hotel in Milwaukee. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions American Family Field and Fiserv Forum are located nearby.

The Pfister Hotel

4.5 out of 5

Price was $1,782, price is now $1,286 per person

$1,286

per person

Sep 27 - Oct 1

found 1 day ago

Roundtrip flight included

Boston (BOS) 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 American Family Field and Fiserv Forum are located nearby.

We try to stay here whenever we are in Milwaukee. The staff is wonderful, rooms clean, beds comfortable and spacious. Great experience and highly recommend.

Reviewed on Aug 27, 2026

The Iron Horse Hotel

4 out of 5

Price was $1,276, price is now $1,025 per person

$1,025

per person

Sep 27 - Oct 1

found 1 day ago

Roundtrip flight included

Boston (BOS) 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 American Family Field and Harley-Davidson Museum are located nearby.

Great and helpful service, place has a great vibe. I had some minor quibbles with the room (TV issues and some bathroom oddities, walls seemed to be a bit thin) but otherwise I enjoyed my brief stay.

Reviewed on Aug 26, 2026

Landing Apartments at Mayfair Collection

4 out of 5

Price was $1,022, price is now $842 per person

$842

per person

Sep 30 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Milwaukee (MKE)

Book a stay at this business-friendly apartment in Milwaukee. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions American Family Field and Mayfair Mall are located nearby.

Instructions to find the Serenity apartments at Wauwatosa Wisconsin weren't great but once we found the actual apartment, it exceeded our expectations. It was truly a home away from home, as it was immaculately clean and had everything needed for a fuss free stay. Shops and restaurants witin walking distance. We highly recommend staying here and will definitely be returning for a longer extended stay!

Reviewed on May 21, 2026

Lake Lawn Resort

3.5 out of 5

Price was $1,019, price is now $847 per person

$847

per person

Oct 14 - Oct 18

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Milwaukee (MKE)

Book a stay at this beach resort in Delavan. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Lake Lawn Resort Marina and Delavan Lake are located nearby.

County Clare Irish Hotel & Pub

2.5 out of 5

Price was $915, price is now $789 per person

$789

per person

Sep 27 - Oct 1

found 1 day ago

Roundtrip flight included

Boston (BOS) 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 American Family Field and Fiserv Forum are located nearby.

Kinn Guesthouse Downtown

4.5 out of 5

Price was $1,117, price is now $977 per person

$977

per person

Sep 27 - Oct 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Milwaukee (MKE)

Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions American Family Field and Harley-Davidson Museum are located nearby.