Find Romantic Hotels in Downtown Sheboygan, Sheboygan from $134

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Check availability on Downtown Sheboygan Romantic Hotels

Our top choices for Downtown Sheboygan romantic hotels

Reception
Watershed Hotel

Watershed Hotel

Watershed Hotel
3.0 star property
Sheboygan
9.8 out of 10, Exceptional, (461)
"Beautiful place I will be staying here anytime I am in Sheboygan "
United States
Matt
$120 nightly
The price is $136
Dec 13 - Dec 14
Total with taxes and fees
Watershed Hotel
Seasonal outdoor pool
Siebkens Resort

Siebkens Resort

Siebkens Resort
3.0 star property
Elkhart Lake
9.2 out of 10, Wonderful, (239)
"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
$119 nightly
The price is $134
Dec 19 - Dec 20
Total with taxes and fees
Siebkens Resort
Lobby
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
$207 nightly
The price is $235
Dec 14 - Dec 15
Total with taxes and fees
Blue Harbor Resort and Conference Center
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
$490 nightly
The price is $541
Dec 14 - Dec 15
Total with taxes and fees
The American Club
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, (254)
"Beautiful view and perfect for our Wisconsin lake getaway."
United States
Holly A.
$276 nightly
The price is $313
Dec 31 - Jan 1, 2026
Total with taxes and fees
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
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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Top Downtown Sheboygan Hotel Reviews

Harbor Winds Hotel

Harbor Winds Hotel

10/10 Excellent
"Could use a better selection of foods. "
Steve 3-night trip
Posted 4 days ago
Harbor Winds Hotel

Frequently asked questions

Searching for romantic hotels in Downtown Sheboygan?
Are you and your partner looking for a romantic getaway? If you'd like to explore some of the area's notable sights, you might make a stop by Stefanie H. Weill Center for the Performing Arts, Above & Beyond Children's Museum, or John Michael Kohler Arts Center. If you'd like to stay close to a particular destination, you can sort properties by neighborhood and proximity to top sights, so you'll be able to see everything on your list.
What is there to do in Downtown Sheboygan?
There's nothing better than experiencing a new place with your sweetheart, so consider taking time to discover all that Downtown Sheboygan has to offer. You might think about stopping by Stefanie H. Weill Center for the Performing Arts, Above & Beyond Children's Museum, or John Michael Kohler Arts Center while you're seeing the sights.

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