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Find Romantic Hotels in Sheboygan, WI

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Check availability on Sheboygan Romantic Hotels

Tonight
Dec 20 - Dec 21
Tomorrow
Dec 21 - Dec 22
Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4

Our top choices for Sheboygan romantic hotels

Lakeside Two Queen Beds | Terrace/patio
Lighthouse Inn

Lighthouse Inn

Lighthouse Inn
2.5 star property
Two Rivers
9.0 out of 10, Wonderful, (1001)
"Great place clean room awesome staff and great food at restaurant "
United States
Jason
The price is ￥14,056
￥15,955 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Lighthouse Inn
Interior detail
Fairway Inn & Suites

Fairway Inn & Suites

Fairway Inn & Suites
3.0 star property
Mishicot
7.8 out of 10, Good, (486)
"Nice staff, had the place basically to ourselves"
United States
Mark
The price is ￥7,851
￥8,910 total
includes taxes & fees
Dec 28 - Dec 29
Fairway Inn & Suites
Exterior
Watershed Hotel

Watershed Hotel

Watershed Hotel
3.0 star property
Sheboygan
9.8 out of 10, Exceptional, (467)
"Beautiful place I will be staying here anytime I am in Sheboygan "
United States
Matt
The price is ￥17,037
￥19,337 total
includes taxes & fees
Dec 22 - Dec 23
Watershed Hotel
Front of property - evening/night
AmericInn by Wyndham Manitowoc

AmericInn by Wyndham Manitowoc

AmericInn by Wyndham Manitowoc
2.5 star property
Manitowoc
8.8 out of 10, Excellent, (947)
"Great, easy & efficient stay"
United States
Alexandra
The price is ￥14,750
￥16,741 total
includes taxes & fees
Jan 1 - Jan 2, 2026
AmericInn by Wyndham Manitowoc
Dining
The Inn on Maritime Bay, an Ascend Collection Hotel

The Inn on Maritime Bay, an Ascend Collection Hotel

The Inn on Maritime Bay, an Ascend Collection Hotel
2.5 star property
Manitowoc
7.6 out of 10, Good, (1000)
"Room was nice and clean, beautiful view of the lake!!"
United States
Emily
The price is ￥19,332
￥21,941 total
includes taxes & fees
Dec 23 - Dec 24
The Inn on Maritime Bay, an Ascend Collection Hotel
Seasonal outdoor pool
Siebkens Resort

Siebkens Resort

Siebkens Resort
3.0 star property
Elkhart Lake
9.2 out of 10, Wonderful, (241)
"I loved the historic atmosphere… short walk to the lake and a quaint on site bar and restaurant. I really enjoyed their house made granola for breakfast."
United States
Jessica
The price is ￥18,772
￥21,120 total
includes taxes & fees
Dec 22 - Dec 23
Siebkens Resort
Fridge, microwave, oven, stovetop
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Sheboygan
9.8 out of 10, Exceptional, (255)
"Beautiful view and perfect for our Wisconsin lake getaway."
United States
Holly A.
The price is ￥22,006
￥49,417 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Breakfast, dinner, brunch served; Regional cuisine, beach views
Blue Harbor Resort and Conference Center

Blue Harbor Resort and Conference Center

Blue Harbor Resort and Conference Center
3.0 star property
Sheboygan
8.4 out of 10, Very Good, (445)
"Nice property right on the water "
United States
bud
The price is ￥29,024
￥37,101 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Blue Harbor Resort and Conference Center
Exterior detail
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
New Holstein
10.0 out of 10, Exceptional, (173)
"Great place would go back"
United States
William
The price is ￥31,944
￥52,841 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
Exterior
The American Club

The American Club

The American Club
5.0 star property
Kohler
9.6 out of 10, Exceptional, (233)
"The shower was amazing "
United States
Patrick
The price is ￥77,298
￥85,414 total
includes taxes & fees
Dec 22 - Dec 23
The American Club
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.
View all properties

Top Sheboygan Hotel Reviews

La Quinta Inn by Wyndham Sheboygan

La Quinta Inn by Wyndham Sheboygan

10/10 Excellent
"Yes "
Robert 2-night trip
Posted 11 days ago
La Quinta Inn by Wyndham Sheboygan
Blue Harbor Resort and Conference Center

Blue Harbor Resort and Conference Center

10/10 Excellent
"Nice property right on the water "
bud 1-night trip
Posted 3 months ago
Blue Harbor Resort and Conference Center

Frequently asked questions

Searching for romantic hotels in Sheboygan?
If you and your partner need some romantic time away, we'd like to help you plan for it. Our guests also love Sheboygan for its array of dining options, golfing, and beautiful lakeside setting. If you'd like to explore some of the area's notable sights, you might make a stop by Lake Michigan, John Michael Kohler Arts Center, or Stefanie H. Weill Center for the Performing Arts. If you'd like to stay close to a certain attraction, you can sort properties by neighborhood and proximity to top sights, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Sheboygan?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Sheboygan: The hottest months are usually August and July with an average temp of 67°F, while the coldest months are February and January with an average of 27°F. The snowiest months in Sheboygan are January, March, February, and October, with each month seeing an average of 7 inches of snowfall.
What is there to do in Sheboygan?
There's nothing better than wandering around a new destination with your sweetheart, so consider checking out all that Sheboygan has to offer. Couples looking for a little of everything will enjoy Sheboygan for its museums, restaurants, and lakeside setting. A visit to Lake Michigan, John Michael Kohler Arts Center, or Stefanie H. Weill Center for the Performing Arts might be just the ticket when you're checking out the sights.