A red lighthouse amidst rough seas with waves crashing against a pier.

Find Hotels with a Pool in Sheboygan, WI

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Check availability on Sheboygan Hotels with a Pool

Our top choices for Sheboygan hotels with a pool

A modern interior with a stone fireplace, seating area, and a flat-screen TV mounted above it.

1. Watershed Hotel

Watershed Hotel
3.0 star property
Sheboygan
9.8 out of 10, Exceptional, (723 reviews)
"Great place in a nice location. Will stay here again."
United States
Tisha
$123 nightly
The price is $140
Nov 15 - Nov 16
Total with taxes and fees
Watershed Hotel
A swimming pool with a no diving sign, chairs around it, and a max pool capacity sign.

2. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,131 reviews)
"Quiet place near the lake."
United States
Vivian
$97 nightly
The price is $110
Nov 18 - Nov 19
Total with taxes and fees
Grandstay Residential Suites Hotel - Sheboygan
A kitchen with dark cabinets, a wooden countertop, and pendant lights.

3. Harbor Winds Hotel

Harbor Winds Hotel
2.0 star property
Sheboygan
8.6 out of 10, Excellent, (1,003 reviews)
"Clean and comfortable very easy to get around the city for the weekend in Sheboygan Knowledgeable friendly staff"
United States
Alecia
$91 nightly
The price is $103
Nov 23 - Nov 24
Total with taxes and fees
Harbor Winds Hotel
A modern kitchen with a marble countertop, a coffee machine, and various food items displayed.

4. La Quinta Inn by Wyndham Sheboygan

La Quinta Inn by Wyndham Sheboygan
3.0 star property
Sheboygan
8.0 out of 10, Very good, (1,003 reviews)
"The staff was very friendly and the room was clean"
United States
Spencer
$92 nightly
The price is $104
Nov 15 - Nov 16
Total with taxes and fees
La Quinta Inn by Wyndham Sheboygan
Restaurant

5. Inn of Sheboygan

Inn of Sheboygan
2.0 star property
Downtown Sheboygan
8.0 out of 10, Very good, (655 reviews)
"Nice hotel for the price and good location."
United States
Anonymous traveler
$1,000 nightly
The price is $1,135
Nov 13 - Nov 14
Total with taxes and fees
Inn of Sheboygan
An indoor swimming pool with lounge chairs and tables, a clear blue pool, and a high ceiling with visible structural beams.

6. Wingate by Wyndham Sheboygan

Wingate by Wyndham Sheboygan
3.0 star property
Downtown Sheboygan
7.0 out of 10, Good, (242 reviews)
"Was ok"
United States
Jason
$70 nightly
The price is $80
Nov 15 - Nov 16
Total with taxes and fees
Wingate by Wyndham Sheboygan
Pool

7. Home2 Suites By Hilton Sheboygan

Home2 Suites By Hilton Sheboygan
3.0 star property
Sheboygan
9.6 out of 10, Exceptional, (161 reviews)
"This has to be one of the cleanest hotels I have ever stayed in. The bed was very comfortable and staff was extremely friendly. Would definitely stay here again!"
United States
Misty
$118 nightly
The price is $134
Nov 22 - Nov 23
Total with taxes and fees
Home2 Suites By Hilton Sheboygan
A spa area with a pool, lounge chairs, and a seating area with a sofa and cushions.

8. The American Club

The American Club
5.0 star property
Kohler
9.6 out of 10, Exceptional, (270 reviews)
"It’s a magical place! Very romantic with historic charm. The attention to detail is impeccable."
United States
Emily
$500 nightly
The price is $553
Nov 15 - Nov 16
Total with taxes and fees
The American Club
A swimming pool with a lifeguard sign, lounge chairs, and a view of the outdoors.

9. Fairfield Inn & Suites by Marriott Sheboygan

Fairfield Inn & Suites by Marriott Sheboygan
3.0 star property
Sheboygan
9.4 out of 10, Exceptional, (307 reviews)
"Nicely kept hotel, great staff, rooms were great! ...And how can you beat happy hour with free beer and wine every day and free breakfast?! I would definitely stay there again."
United States
Lawrence
$122 nightly
The price is $139
Nov 27 - Nov 28
Total with taxes and fees
Fairfield Inn & Suites by Marriott Sheboygan
A hotel room with a bed, bedside tables, a desk, a chair, and a window with curtains.

10. Hampton Inn Manitowoc

Hampton Inn Manitowoc
2.5 star property
Manitowoc
9.6 out of 10, Exceptional, (40 reviews)
"Second time staying there, Everything was great , helpful front desk, clean hotel , quite rooms , nice walk-in shower , excellent breakfast"
United States
Richard
$118 nightly
The price is $134
Nov 22 - Nov 23
Total with taxes and fees
Hampton Inn Manitowoc
A hotel with a curved facade, illuminated signage, and snow-covered surroundings.

11. Inn On Woodlake

Inn On Woodlake
3.5 star property
Kohler
9.4 out of 10, Exceptional, (293 reviews)
"Great place to stay."
United States
Peter
$229 nightly
The price is $253
Nov 15 - Nov 16
Total with taxes and fees
Inn On Woodlake
A large outdoor swimming pool with lounge chairs and umbrellas, surrounded by a building with multiple windows and a covered patio area.

12. Siebkens Resort

Siebkens Resort
3.0 star property
Elkhart Lake
9.2 out of 10, Wonderful, (312 reviews)
"Great old school hotel with racing history."
United States
Samuel
$107 nightly
The price is $121
Dec 1 - Dec 2
Total with taxes and fees
Siebkens Resort
A swimming pool area with lounge chairs and umbrellas, a pool building with a sign, and a multi-story building in the background.

13. The Osthoff Resort

The Osthoff Resort
3.5 star property
Elkhart Lake
9.2 out of 10, Wonderful, (517 reviews)
"Beautiful and clean property…perfect get away from the city!!"
United States
Stephen
$251 nightly
The price is $283
Nov 15 - Nov 16
Total with taxes and fees
The Osthoff Resort
An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled deck.

14. Baymont by Wyndham Plymouth

Baymont by Wyndham Plymouth
2.5 star property
Plymouth
9.0 out of 10, Wonderful, (619 reviews)
"The staff was friendly and helpful during both check in and check out. Our room was clean and comfortable."
United States
Traci
$125 nightly
The price is $142
Nov 30 - Dec 1
Total with taxes and fees
Baymont by Wyndham Plymouth
An indoor swimming pool with a mural of a coastal scene, a lounge area with chairs, and a small table.

15. Lighthouse Inn

Lighthouse Inn
2.5 star property
Two Rivers
9.0 out of 10, Wonderful, (1,000 reviews)
"It was a great stay"
United States
Christa
$99 nightly
The price is $112
Nov 29 - Nov 30
Total with taxes and fees
Lighthouse Inn
An indoor swimming pool with clear blue water, surrounded by white chairs and tables, and large windows offering views of the outdoors.

16. Holiday Inn Express Sheboygan-Kohler by IHG

Holiday Inn Express Sheboygan-Kohler by IHG
2.5 star property
Sheboygan
8.8 out of 10, Excellent, (412 reviews)
"Clean property. Close to shopping centers."
United States
Ka
$105 nightly
The price is $119
Nov 15 - Nov 16
Total with taxes and fees
Holiday Inn Express Sheboygan-Kohler by IHG
A spacious dining area with white chairs and tables, large windows with blinds, and a view of the outdoors.

17. Harbor Town, BW Signature Collection

Harbor Town, BW Signature Collection
2.5 star property
Manitowoc
8.8 out of 10, Excellent, (1,004 reviews)
"nice place and a good breakfast"
United States
Patrick
$73 nightly
The price is $83
Nov 18 - Nov 19
Total with taxes and fees
Harbor Town, BW Signature Collection
An indoor swimming pool with clear glass walls, wooden ceiling beams, and a poolside seating area with chairs and potted plants.

18. Best Western Stanton Inn

Best Western Stanton Inn
2.5 star property
Chilton
9.0 out of 10, Wonderful, (579 reviews)
"Staff was very friendly . Hotel was very clean great breakfast and the pool looked wonderful. We will be back"
United States
Jennifer
$132 nightly
The price is $139
Nov 15 - Nov 16
Total with taxes and fees
Best Western Stanton Inn
An indoor swimming pool with wooden walls and ceiling, surrounded by tables and chairs.

19. AmericInn by Wyndham Manitowoc

AmericInn by Wyndham Manitowoc
3.0 star property
Manitowoc
8.8 out of 10, Excellent, (1,009 reviews)
"Decent breakfast, clean and comfortable room, friendly staff."
United States
Hongmei
$84 nightly
The price is $96
Nov 18 - Nov 19
Total with taxes and fees
AmericInn by Wyndham Manitowoc
A swimming pool with clear no diving signs, a changing room, and a door marked "EXIT".

20. Cobblestone Hotel & Suites - Two Rivers

Cobblestone Hotel & Suites - Two Rivers
3.0 star property
Two Rivers
8.8 out of 10, Excellent, (1,004 reviews)
"Very nice little hotel. The staff was super helpful and allowed us to check in early to get ready for a wedding."
United States
Rocky
$109 nightly
The price is $123
Dec 1 - Dec 2
Total with taxes and fees
Cobblestone Hotel & Suites - Two Rivers
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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Choose what matters most at hotels with a pool in Sheboygan

Breakfast included
Hot tub

Hotels with pools and free breakfast in Sheboygan

A spacious living area with a stone fireplace, comfortable seating, and a balcony with a railing.
AmericInn by Wyndham Sheboygan

AmericInn by Wyndham Sheboygan

AmericInn by Wyndham Sheboygan
3.0 star property
Sheboygan
8.4 out of 10, Very good, (1007)
$84 nightly
The price is $96
Nov 18 - Nov 19
Total with taxes and fees
AmericInn by Wyndham Sheboygan
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Hotels with pools and hot tubs in Sheboygan

A hotel with a modern design, featuring a prominent tower with the hotel name, a covered entrance, and a well-maintained lawn.
Comfort Inn & Suites Sheboygan I-43

Comfort Inn & Suites Sheboygan I-43

Comfort Inn & Suites Sheboygan I-43
2.5 star property
Sheboygan
8.4 out of 10, Very good, (296)
$78 nightly
The price is $88
Dec 8 - Dec 9
Total with taxes and fees
Comfort Inn & Suites Sheboygan I-43
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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Find out more about Sheboygan

Discover top Sheboygan attractions

Sheboygan offers a delightful mix of adventure and relaxation for travelers looking to explore the beauty of the Wisconsin shoreline. Start your day with a stroll along the picturesque Lake Michigan shoreline, where stunning views and sandy beaches invite you to unwind. For those seeking a bit of excitement, the nearby scenic trails provide a perfect opportunity for biking or walking while soaking in the natural beauty of the area. Art enthusiasts can discover the vibrant local art scene by visiting unique galleries and studios that showcase the talent of local artists. Families will appreciate the interactive experiences available at various local attractions that engage children and adults alike. Lastly, don’t miss the chance to savor Sheboygan's renowned culinary offerings, from fresh seafood to farm-to-table cuisine, ensuring a memorable dining experience. After a day of exploration, consider staying in one of the charming accommodations that not only provide comfort but also enhance your overall experience with attentive service and local insights.

Top Sheboygan Hotel Reviews

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

10/10 Excellent
"Was a very nice stay, hotel room was nice and staff was very helpful and friendly. Will definitely be coming back"
Maxim 1-night trip
Posted 2 hours ago
Grandstay Residential Suites Hotel - Sheboygan

Frequently asked questions

How much does a hotel with outdoor pool in Sheboygan cost?
Enjoy staying in a hotel in Sheboygan with an outdoor pool. You can find a great deal from $81 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
What are some of the best Sheboygan hotels with outdoor pools and scenic views?
Blue Harbor Resort and Conference Center is a fantastic choice for travellers seeking an unforgettable stay in Sheboygan. This 3-star resort not only boasts a stunning outdoor pool but also offers scenic views of the beautiful lake, making it a great backdrop for relaxation and fun.

Families will appreciate the array of amenities designed to enhance their experience. The outdoor pool features inviting sun loungers and poolside cabanas, allowing for leisurely days under the sun. For added excitement, there's even a waterslide that kids (and adults.) will love. Guests rave about the friendly and professional staff, ensuring an inviting space throughout their stay.

With a review score of 8.4, travellers frequently highlight the spacious rooms and lovely balconies that provide a great spot to take in the lake views.
Is it cheaper to book flights and a Sheboygan hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Sheboygan for you.

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