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

Find Hotels with a Pool in Sheboygan, WI

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Check availability on Sheboygan Hotels with a Pool

Tonight
Oct 2 - Oct 3
Tomorrow
Oct 3 - Oct 4
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Sheboygan hotels with a pool

A swimming pool area with lounge chairs and umbrellas.
A spacious lobby with a central chandelier, multiple levels with balconies, and rows of blue chairs.
A beachfront hotel with multiple red-roofed buildings, a sandy path leading to the beach, and clear blue water.
A coastal hotel with a wooden boardwalk leading to beach chairs.

1. Blue Harbor Resort and Conference Center

Blue Harbor Resort and Conference Center
Sheboygan
  • Poolside paradise awaits at this beachfront resort with indoor and outdoor options for year-round splashing fun.
$207 nightly
$235 total
Oct 4 - Oct 5
Total with taxes and fees
Blue Harbor Resort and Conference Center
A swimming pool with a no diving sign, chairs around it, and a max pool capacity sign.
A spacious dining area with multiple wooden tables and chairs, a ceiling fan, and a bar area in the background.
A hotel room with two beds, a sofa, a TV, and a dining table.
A spacious living area with a fireplace, a sofa, and a dining area in the background.

2. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
Downtown Sheboygan
  • Splash into tranquil waters at this Sheboygan retreat with a pristine indoor pool.
$123 nightly
$140 total
Oct 21 - Oct 22
Total with taxes and fees
Grandstay Residential Suites Hotel - Sheboygan
An indoor swimming pool with a mural of a coastal scene, a lounge area with chairs, and a small table.
A living room with a view of the sea, a sofa, a wooden table, and a painting on the wall.
A view from a window overlooking a coastal area with a pathway leading to a building with a balcony.
A modern building with large windows, a pathway lined with rocks, and a view of the sea.

3. Lighthouse Inn

Lighthouse Inn
Two Rivers
  • Lakeside relaxation awaits with a private beach and stunning indoor pool, just steps from white sand shores of Lake Michigan.
$105 nightly
$119 total
Nov 1 - Nov 2
Total with taxes and fees
Lighthouse Inn
An indoor swimming pool with lounge chairs and tables, a clear blue pool, and a high ceiling with visible structural beams.
A reception area with a wooden reception desk, a flat-screen TV, and a seating area with two chairs and a small table.
A restaurant with multiple dining tables, chairs, and a bar area.
A conference room with a long table, six chairs, and a wooden accent wall.

4. Wingate by Wyndham Sheboygan

Wingate by Wyndham Sheboygan
Downtown Sheboygan
  • Dive into lakeside adventures with an indoor pool, arcade, and hiking trails nearby.
$93 nightly
$106 total
Nov 1 - Nov 2
Total with taxes and fees
Wingate by Wyndham Sheboygan
A family sitting by a poolside with chairs and a tiled wall in the background.
A coffee station with a chalkboard sign reading "Welcome to the Beginning of Day!" and various coffee-making equipment.
A spacious living area with a stone fireplace, comfortable seating, and a balcony with a railing.
A hotel room with a bed, a desk with a sink, a chair, a small table, and a window with curtains.

5. AmericInn by Wyndham Sheboygan

AmericInn by Wyndham Sheboygan
Sheboygan
  • Splash into warmth and comfort at this hotel's indoor pool oasis with year-round swim escapes.
$86 nightly
$97 total
Nov 1 - Nov 2
Total with taxes and fees
AmericInn by Wyndham Sheboygan
An indoor swimming pool with wooden walls and ceiling, surrounded by white lounge chairs and tables.
A hotel room with a bed, a sofa, a desk, and a television.
A hotel dining area with tables, chairs, a reception desk, and a ceiling fan.
A bathroom with a sink, mirror, towel rack, and toilet.

6. Quality Inn Sheboygan North I-43

Quality Inn Sheboygan North I-43
Sheboygan
  • Pool paradise awaits at this inviting hotel, where year-round swimming meets pure relaxation.
$84 nightly
$96 total
Nov 1 - Nov 2
Total with taxes and fees
Quality Inn Sheboygan North I-43
An indoor swimming pool with a geometric ceiling design, a seating area with chairs, and a view of the outdoors through large windows.
A multi-story hotel with a modern design, featuring a covered outdoor seating area and a visible fire feature.
A modern hotel room with two beds, a desk, and a view of the outdoors.
A buffet counter with a coffee machine, a display case with food, and a digital menu board.

7. Home2 Suites By Hilton Sheboygan

Home2 Suites By Hilton Sheboygan
Sheboygan
  • Sleek indoor pool oasis minutes from Lake Michigan creates a serene retreat for year-round swimming at this modern hotel.
$139 nightly
$157 total
Oct 25 - Oct 26
Total with taxes and fees
Home2 Suites By Hilton Sheboygan
A swimming pool area with lounge chairs and umbrellas, a pool building with a sign, and a multi-story building in the background.
A large building with a stone entrance, two flags, and a sign that reads 'The Osborn.'
A restaurant with tables set for dining, candles, and framed pictures on the walls.
A banquet hall with round tables, candles, and a central floral arrangement.

8. The Osthoff Resort

The Osthoff Resort
Elkhart Lake
  • Splash into relaxation at this lakeside resort offering indoor and outdoor pools for year-round swimming.
$251 nightly
$283 total
Oct 4 - Oct 5
Total with taxes and fees
The Osthoff Resort
An indoor swimming pool with clear water, tiled floor, and safety railings.
A hotel with a modern design, featuring a prominent tower with the hotel name, a covered entrance, and a well-maintained lawn.
A hotel room with a sofa, a small round table, a bed, a desk, and a lamp.
A hotel room with two beds, a desk, a chair, a sofa, and a round yellow table.

9. Comfort Inn & Suites Sheboygan I-43

Comfort Inn & Suites Sheboygan I-43
Sheboygan
  • Aquatic paradise features waterslide, children's pool, and hot tub for family fun all day long.
$86 nightly
$98 total
Nov 2 - Nov 3
Total with taxes and fees
Comfort Inn & Suites Sheboygan I-43
A swimming pool with a lifeguard sign, lounge chairs, and a view of the outdoors.
An outdoor patio with stone walls, a fire feature, and seating.
A reception area with a wooden reception desk, a digital display, and a refrigerator stocked with beverages.
A modern hotel entrance with a curved canopy, multiple floors, and a prominent sign.

10. Fairfield Inn & Suites by Marriott Sheboygan

Fairfield Inn & Suites by Marriott Sheboygan
Sheboygan
  • Dive into year-round aquatic bliss at this lakeside retreat with a pristine indoor pool just minutes from Lake Michigan.
$118 nightly
$134 total
Oct 30 - Oct 31
Total with taxes and fees
Fairfield Inn & Suites by Marriott Sheboygan
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Choose what matters most at hotels with a pool in Sheboygan

Breakfast included
Hot tub
Water park
4 stars
Spa

Hotels with pools and free breakfast in Sheboygan

A spacious living area with a fireplace, a sofa, and a dining area in the background.
A swimming pool with a no diving sign, chairs around it, and a max pool capacity sign.
A hotel room with two beds, a sofa, a TV, and a dining table.
A spacious dining area with multiple wooden tables and chairs, a ceiling fan, and a bar area in the background.

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
Downtown Sheboygan
$123 nightly
$140 total
Oct 21 - Oct 22
Total with taxes and fees
Grandstay Residential Suites Hotel - Sheboygan
A modern hotel entrance with a curved canopy, multiple floors, and a prominent sign.
A reception area with a wooden reception desk, a digital display, and a refrigerator stocked with beverages.
A swimming pool with a lifeguard sign, lounge chairs, and a view of the outdoors.
An outdoor patio with stone walls, a fire feature, and seating.

Fairfield Inn & Suites by Marriott Sheboygan

Fairfield Inn & Suites by Marriott Sheboygan
Sheboygan
$118 nightly
$134 total
Oct 30 - Oct 31
Total with taxes and fees
Fairfield Inn & Suites by Marriott Sheboygan
A Holiday Inn Express hotel with a brick facade, a covered entrance, and an American flag.
An indoor swimming pool with clear blue water, surrounded by white chairs and tables, and large windows offering views of the outdoors.
A modern dining area with a central island, bar stools, and a sofa.
A hotel room with a sofa, a desk, a chair, a television, and a window with curtains.

Holiday Inn Express Sheboygan-Kohler by IHG

Holiday Inn Express Sheboygan-Kohler by IHG
Sheboygan
$127 nightly
$144 total
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Express Sheboygan-Kohler by IHG
A spacious living area with a stone fireplace, comfortable seating, and a balcony with a railing.
A family sitting by a poolside with chairs and a tiled wall in the background.
A coffee station with a chalkboard sign reading "Welcome to the Beginning of Day!" and various coffee-making equipment.
A hotel room with a bed, a desk with a sink, a chair, a small table, and a window with curtains.

AmericInn by Wyndham Sheboygan

AmericInn by Wyndham Sheboygan
Sheboygan
$86 nightly
$97 total
Nov 1 - Nov 2
Total with taxes and fees
AmericInn by Wyndham Sheboygan
An outdoor patio area with tables and chairs, string lights, and a view of the building in the background.
An indoor swimming pool with a geometric ceiling design, a seating area with chairs, and a view of the outdoors through large windows.
A modern hotel room with two beds, a desk, and a view of the outdoors.
A buffet counter with a coffee machine, a display case with food, and a digital menu board.

Home2 Suites By Hilton Sheboygan

Home2 Suites By Hilton Sheboygan
Sheboygan
$139 nightly
$157 total
Oct 25 - Oct 26
Total with taxes and fees
Home2 Suites By Hilton Sheboygan
A hotel with a modern design, featuring a prominent tower with the hotel name, a covered entrance, and a well-maintained lawn.
An indoor swimming pool with clear water, tiled floor, and safety railings.
A hotel room with a sofa, a small round table, a bed, a desk, and a lamp.
A hotel room with two beds, a desk, a chair, a sofa, and a round yellow table.

Comfort Inn & Suites Sheboygan I-43

Comfort Inn & Suites Sheboygan I-43
Sheboygan
$86 nightly
$98 total
Nov 2 - Nov 3
Total with taxes and fees
Comfort Inn & Suites Sheboygan I-43
A hotel with a curved facade, illuminated signage, and snow-covered surroundings.
A cozy living room with a fireplace, leather furniture, and a chandelier.
A spa area with a green heated floor, a ceiling with a cloud mural, and two relaxation chairs on either side.
Two people sitting on a couch facing a fireplace with a fruit platter on the table.

Inn On Woodlake

Inn On Woodlake
Kohler
$229 nightly
$253 total
Nov 1 - Nov 2
Total with taxes and fees
Inn On Woodlake
A large, historic building with multiple chimneys and a prominent American flag.
A spacious indoor area with multiple seating arrangements, including chairs and sofas, and a bar area with shelves.
A large indoor pool with a waterfall feature, surrounded by white chairs and a large towel rack.
A coastal golf course with a view of the ocean.

The American Club

The American Club
Kohler
$500 nightly
$553 total
Nov 1 - Nov 2
Total with taxes and fees
The American Club
An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled deck.
A reception area with a Baymont Inn & Suites sign, a reception desk, a small round table, and a decorative wreath.
A hotel room with a flat-screen TV, a desk with a chair, a bed, a sofa, and a large window with curtains.
A hotel room with two beds, a desk with a computer, a TV, and a window with curtains.

Baymont by Wyndham Plymouth

Baymont by Wyndham Plymouth
Plymouth
$119 nightly
$135 total
Oct 15 - Oct 16
Total with taxes and fees
Baymont by Wyndham Plymouth
An indoor swimming pool with wooden walls and ceiling, surrounded by white lounge chairs and tables.
A hotel room with a bed, a sofa, a desk, and a television.
A hotel dining area with tables, chairs, a reception desk, and a ceiling fan.
A pathway leading to a building with a patio area, surrounded by sunflowers and marigolds.

Quality Inn Sheboygan North I-43

Quality Inn Sheboygan North I-43
Sheboygan
$84 nightly
$96 total
Nov 1 - Nov 2
Total with taxes and fees
Quality Inn Sheboygan North I-43
View all properties

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.
An indoor swimming pool with clear water, tiled floor, and safety railings.
A hotel room with a sofa, a small round table, a bed, a desk, and a lamp.
A hotel room with two beds, a desk, a chair, a sofa, and a round yellow table.

Comfort Inn & Suites Sheboygan I-43

Comfort Inn & Suites Sheboygan I-43
Sheboygan
$86 nightly
$98 total
Nov 2 - Nov 3
Total with taxes and fees
Comfort Inn & Suites Sheboygan I-43
An indoor swimming pool with wooden walls and ceiling, surrounded by white lounge chairs and tables.
A hotel room with a bed, a sofa, a desk, and a television.
A hotel dining area with tables, chairs, a reception desk, and a ceiling fan.
A pathway leading to a building with a patio area, surrounded by sunflowers and marigolds.

Quality Inn Sheboygan North I-43

Quality Inn Sheboygan North I-43
Sheboygan
$84 nightly
$96 total
Nov 1 - Nov 2
Total with taxes and fees
Quality Inn Sheboygan North I-43
A spacious atrium with a grand chandelier, multiple balconies, and large windows allowing natural light.
A large, white building with a symmetrical facade and multiple balconies.
A coastal hotel with a wooden boardwalk leading to beach chairs.
A spacious lobby with a central chandelier, multiple levels with balconies, and rows of blue chairs.

Blue Harbor Resort and Conference Center

Blue Harbor Resort and Conference Center
Sheboygan
$207 nightly
$235 total
Oct 4 - Oct 5
Total with taxes and fees
Blue Harbor Resort and Conference Center
An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled deck.
A reception area with a Baymont Inn & Suites sign, a reception desk, a small round table, and a decorative wreath.
A hotel room with a flat-screen TV, a desk with a chair, a bed, a sofa, and a large window with curtains.
A hotel room with two beds, a desk with a computer, a TV, and a window with curtains.

Baymont by Wyndham Plymouth

Baymont by Wyndham Plymouth
Plymouth
$119 nightly
$135 total
Oct 15 - Oct 16
Total with taxes and fees
Baymont by Wyndham Plymouth
An indoor swimming pool with clear blue water, tiled walls, and large windows offering a view of a field.
A bar area with a long counter, multiple stools, and a selection of beverages.
A spacious lobby with marble flooring, vending machines, and a staircase.
A neatly made bed with white bedding, two bedside lamps, a dark headboard, and a small bedside table with a phone and a lamp.

The Oasis Hotel & Bar

The Oasis Hotel & Bar
Sheboygan Falls
$71 nightly
$79 total
Oct 18 - Oct 19
Total with taxes and fees
The Oasis Hotel & Bar
Indoor pool
Lobby
A restaurant with stone walls, a flat-screen TV, a fireplace, and a kitchen area with a water dispenser and coffee machines.
Room

AmericInn by Wyndham Plymouth

AmericInn by Wyndham Plymouth
Plymouth
$111 nightly
$125 total
Nov 2 - Nov 3
Total with taxes and fees
AmericInn by Wyndham Plymouth
A large building with a stone entrance, two flags, and a sign that reads 'The Osborn.'
A spacious lobby with a high ceiling, chandeliers, a stone fireplace, and a blue patterned carpet.
A restaurant with tables set for dining, candles, and framed pictures on the walls.
A swimming pool area with lounge chairs and umbrellas, a pool building with a sign, and a multi-story building in the background.

The Osthoff Resort

The Osthoff Resort
Elkhart Lake
$251 nightly
$283 total
Oct 4 - Oct 5
Total with taxes and fees
The Osthoff Resort
A hotel lobby with a glass door leading to a pool area.
Room
A hotel room with a sofa, armchair, and a small table. There is a mirror on the wall and a lamp. The room has a carpeted floor and a picture of a sunset on the wall.
A living room with two couches, a coffee table, and a round mirror on the wall.

Holiday Inn Manitowoc by IHG

Holiday Inn Manitowoc by IHG
Manitowoc
$87 nightly
$99 total
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Manitowoc by IHG
A view from a window overlooking a coastal area with a pathway leading to a building with a balcony.
A lobby with a wooden staircase, a reception desk, and a seating area with a sofa and chairs.
A restaurant with wooden tables and chairs, large windows with a view of the sea, and hanging pendant lights.
A living room with a view of the sea, a sofa, a wooden table, and a painting on the wall.

Lighthouse Inn

Lighthouse Inn
Two Rivers
$105 nightly
$119 total
Nov 1 - Nov 2
Total with taxes and fees
Lighthouse Inn
An indoor swimming pool with clear water, wooden walls, and a tiled floor.
A modern living room with a grey sofa, a wooden coffee table, and a dining area with a wooden table and chairs.
A garden with a bench, a tree, and a view of the water.
A hotel room with a bed, a fireplace, a television, a sauna, a dining table, and a kitchen area.

Village Inn on the Lake

Village Inn on the Lake
Two Rivers
$90 nightly
$102 total
Oct 19 - Oct 20
Total with taxes and fees
Village Inn on the Lake
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 Sheboygan Hotel Reviews

Wingate by Wyndham Sheboygan

Wingate by Wyndham Sheboygan

8/10 Good
"Glad for the last minute availability."
Samantha F 2-night trip
Posted 3 days ago
Wingate by Wyndham Sheboygan
Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

8/10 Good
"Really charming little room. Comfy, clean, full size fridge, a microwave, basic dishes. A person could easily stay here awhile. Perfect location to walk to the Kohler Art Center, dine at the Black Pig and even walk to the lighthouse! Would rate higher, but I was double billed...once by Expedia and again by the front desk at check in. I called about it once I was home and the front desk gal was pleasant, admitted there had been an error and will refund me accordingly. No issues in resolving."
Susan 1-night trip
Posted 5 days ago
Grandstay Residential Suites Hotel - Sheboygan
Comfort Inn & Suites Sheboygan I-43

Comfort Inn & Suites Sheboygan I-43

8/10 Good
"Breakfast was incredible. Staff was helpful. The pool had red sediment/staining presumably iron deposits? Overall felt clean but could smell animals throughout and room was musty at first until we got used to it"
MELISSA M 2-night trip
Posted 5 days ago
Comfort Inn & Suites Sheboygan I-43
Holiday Inn Express Sheboygan-Kohler by IHG

Holiday Inn Express Sheboygan-Kohler by IHG

10/10 Excellent
"Clean property. Close to shopping centers."
Ka 4-night trip
Posted 5 days ago
Holiday Inn Express Sheboygan-Kohler by IHG
Blue Harbor Resort and Conference Center

Blue Harbor Resort and Conference Center

10/10 Excellent
"Perfect weekend getaway spent looking out the balcony at the beach waves!"
Alexis 1-night trip
Posted 6 days ago
Blue Harbor Resort and Conference Center
Super 8 by Wyndham Sheboygan WI

Super 8 by Wyndham Sheboygan WI

8/10 Good
"Fair pricing, been in worse for a lot more money. Beds were a bit hard, showers were hot, reserved an accessable room, apparently that means it's on the first floor. No grab bars in the shower or by the toilet. Good for the price."
Dana 4-night trip
Posted 11 days ago
Super 8 by Wyndham Sheboygan WI

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 $79 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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