Downtown Sheboygan Holidays from £1,091

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Your Downtown Sheboygan Holiday

Take the stress out of organising your next break by booking a Downtown Sheboygan holiday package. Immerse yourself in the sights and sounds of this appealing neighbourhood and enjoy all it has to offer. Wondering what to see and do during your trip to Downtown Sheboygan? Nearby attractions like Blue Harbour Resort & Conference Centre Water Park, John Michael Kohler Arts Centre and Stefanie H. Weill Centre for the Performing Arts are good places to begin. Don't just imagine it — turn it into a reality! Secure your ideal Downtown Sheboygan holiday with Expedia and experience travel your way.

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Pleasant Prairie Kenosha

Days Inn by Wyndham Pleasant Prairie Kenosha

2.5 out of 5
Price was £1,121, price is now £1,091 per person
£1,091
per person
13 Jun - 20 Jun
found 1 day ago
Return flight included
London (LHR) to Milwaukee (MKE)
8.4/10 Very Good! (424 reviews)
Breakfast and staff were great. We had hair that was not ours in the bathroom and only one washcloth for 2 of us. When I spoke with the front desk they were very accomdating and refunded us some of our cost. It should also be noted that there is no elevator in this hotel.

Reviewed on 6 May 2026

Holiday Inn Express Hotel & Suites Pleasant Prairie-Kenosha by IHG

Holiday Inn Express Hotel & Suites Pleasant Prairie-Kenosha by IHG

2.5 out of 5
Price was £1,421, price is now £1,316 per person
£1,316
per person
13 Jun - 20 Jun
found 1 day ago
Return flight included
London (LHR) to Milwaukee (MKE)
8.8/10 Excellent! (553 reviews)
Everything was very good

Reviewed on 29 Mar 2026

Fairfield Inn & Suites Kenosha Pleasant Prairie

Fairfield Inn & Suites Kenosha Pleasant Prairie

3 out of 5
Price was £1,427, price is now £1,367 per person
£1,367
per person
13 Jun - 20 Jun
found 1 day ago
Return flight included
London (LHR) to Milwaukee (MKE)
9.2/10 Wonderful! (715 reviews)
This is normally our favorite hotel in the area, Fairfield is the best chain IMO...this time we were disappointed. There was some sort of baseball event going on, the place was crowded with teenagers. It was very noisy. Parents were loud too. Kids running the halls at night, left garbage in the breakfast area. Our lock on our door didn't work so they switched our room. We didn't realize the lock didn't work until we went to go out to eat, already had showered and unpacked but they gave us a different room. Staff was helpful.

Reviewed on 27 Apr 2026

Top hotels in Downtown Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

2.5 out of 5
708 Niagara Avenue Sheboygan WI
Fully refundableReserve now, pay when you stay
The price is £99 per night from 17 May to 18 May
£99
17 May - 18 May
includes taxes & fees
8.6/10 Excellent! (1,030 reviews)
Check in took too long. One girl working me about 6-8 people waiting in line.

Reviewed on 26 Apr 2026

Grandstay Residential Suites Hotel - Sheboygan
Wingate by Wyndham Sheboygan

Wingate by Wyndham Sheboygan

3 out of 5
723 Center Avenue Sheboygan WI
Fully refundableReserve now, pay when you stay
The price is £61 per night from 21 May to 22 May
£61
21 May - 22 May
includes taxes & fees
7.2/10 Good! (177 reviews)
The room was clean and quiet. Parking was good, even on the weekend when the lot was almost full it was not a long walk. The pool area was clean and the water temperature in the pool was comfortable. If I had a complaint at all it would be low water pressure in the shower. Good chance it is an eco ...

Reviewed on 12 May 2026

Wingate by Wyndham Sheboygan
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Sheboygan WI
The price is £210 per night from 14 May to 15 May
£210
14 May - 15 May
includes taxes & fees
10/10 Exceptional! (13 reviews)
The stay was great ! Had lots of fun definitely will be back .

Reviewed on 28 Mar 2026

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
See all 455 properties in Downtown Sheboygan
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.
All Inclusive Holidays
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Family Friendly Holidays

Frequently asked questions

How much does a Downtown Sheboygan travel package cost?
Get your credit card ready, because a trip to Downtown Sheboygan starts from only £1,091. When you combine your hotels, flights and car rentals into a package, you'll pick up great deals.
If I'm not able to travel, can I cancel my Downtown Sheboygan travel package?
Because we know life can be unpredictable, the answer is yes. For further details, check out our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to change or cancel it for free. Your airline, hotel or car rental company may charge a fee if you made your booking a while ago.
How do I get a cheap travel package to Downtown Sheboygan?
Simply by bundling. Flights, hotels and rental cars — combine whatever you need into a Downtown Sheboygan travel package to save loads of cash. Score even more discounts when you include extras such as tours or experiences to your booking. But that's not the only good part. You have the freedom to customize your trip your way. We offer more than 550 air carriers and 1,000,000 hotel options all over the world, so that everyone has an opportunity to travel and fulfil those holiday fantasies.
Does Expedia offer Book Now, Pay Later Downtown Sheboygan holidays?
We do. Expedia has joined forces with online lender Klarna to help you easily pay for your holiday in instalments. Simply pick the payment plan that suits you best during the checkout process and take the stress out of budgeting for your trip. Remember to bundle your accommodation, car hire and flights with Expedia to get the biggest bang for your buck. Check out our flexible payment options below:

  • Pay monthly holidays: Klarna has convenient monthly payment plans that work for all budgets, so you can book that well-deserved holiday now.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay for your trip over multiple transactions.
  • Low deposit holidays: If paying a small percentage of your trip (rather than all of it upfront) makes it easier to click that "book now" button, consider a low deposit holiday payment plan with Klarna.

Where should I stay in Downtown Sheboygan?
With interesting attractions such as Blue Harbour Resort & Conference Centre Water Park and University of Wisconsin-Sheboygan in this neighbourhood, try to find a hotel situated near either of them. Stefanie H. Weill Centre for the Performing Arts is another sight that travellers flock to.
What are the top hotels in Downtown Sheboygan?
La Quinta Inn by Wyndham Sheboygan and Super 8 by Wyndham Sheboygan WI are two of the most popular hotels in Downtown Sheboygan. Why not look up the amenities and facilities at each and then make a decision?
How far in advance should I book my Downtown Sheboygan holiday?
To bag cheap prices, book as early as you can. Airlines generally release flights, along with some of the lowest fares, nearly a year prior to departure. Hotels, experiences and car rental should also be booked early to avoid disappointment. If you've decided on a last-minute getaway in Downtown Sheboygan, there are always plenty of great deals on Expedia. Book your escape today!
What does an Expedia Downtown Sheboygan travel package include?
Rental cars, flights and hotels, or any combination of them — it's your choice. Whether you're venturing to Downtown Sheboygan with the entire family or adventuring with your friends, there's a bundle to match every budget and style. Once you've made your booking, why not add on one or two tours or activities?
What should I know before booking a Downtown Sheboygan travel package?
When you book your flights, hotels and car rentals together, you'll score awesome discounts. Whether you're planning a beach escape in a villa or would rather stay in a cosy apartment in the city, Expedia will help make it happen.
Can I choose my airline with a Downtown Sheboygan Expedia travel package?
The choice is all yours! We offer more than 550 airlines worldwide, so you can tailor your Downtown Sheboygan trip according to your needs and budget.

Things to do

Sheboygan Showdown Scavenger Hunt

Sheboygan Showdown Scavenger Hunt

£21
per adult
Sheboygan Showdown Scavenger Hunt
Sheboygan Arts & Water Segway Tour w/ Private Tour Option

Sheboygan Segway Tour w/ Private Tour Option

£74
per adult
Sheboygan Segway Tour w/ Private Tour Option
Private Professional Golf Experience in American Club Wisconsin

Private Professional Golf Experience in American Club Wisconsin

£164
per adult
Private Professional Golf Experience in American Club Wisconsin
See all activities in Sheboygan

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.