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Find Hotels with a Pool in Sheboygan, WI

Check availability on Sheboygan Hotels with a Pool

Tonight
Oct 5 - Oct 6
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Oct 6 - Oct 7
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Sheboygan hotels with a pool

A swimming pool area with lounge chairs and umbrellas.
A spacious atrium with a grand chandelier, multiple balconies, and large windows allowing natural light.
A beachfront hotel with multiple red-roofed buildings, a sandy path leading to the beach, and clear blue water.
A spacious lobby with a central chandelier, multiple levels with balconies, and rows of blue 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 7 - Oct 8
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 spacious living area with a fireplace, a sofa, and a dining area in the background.
A hotel room with two beds, a sofa, a TV, and a dining table.

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.
$133 nightly
$151 total
Nov 5 - Nov 6
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 modern building with large windows, a pathway lined with rocks, and a view of the sea.
A view from a window overlooking a coastal area with a pathway leading to a building with a balcony.
A living room with a view of the sea, a sofa, a wooden table, and a painting on the wall.

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 conference room with a long table, six chairs, and a wooden accent wall.
A hotel room with two beds, a desk, a chair, a TV, and an air conditioning unit.
A reception area with a wooden reception desk, a flat-screen TV, and a seating area with two chairs and a small table.

4. Wingate by Wyndham Sheboygan

Wingate by Wyndham Sheboygan
Downtown Sheboygan
  • Dive into lakeside adventures with an indoor pool, arcade, and hiking trails nearby.
$85 nightly
$97 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 hotel room with a bed, a desk with a sink, a chair, a small table, and a window with curtains.
A reception area with two desks, a TV, and orange chairs.

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 painting on the wall.
A hotel dining area with tables, chairs, a reception desk, and a ceiling fan.
A hotel room with a bed, a sofa, a desk, and a television.

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.
$80 nightly
$91 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 buffet counter with a coffee machine, a display case with food, and a digital menu board.
An outdoor patio area with tables and chairs, string lights, and a view of the building in the background.
A multi-story hotel with a modern design, featuring a covered outdoor seating area and a visible fire feature.

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 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.
A large building with a stone entrance, two flags, and a sign that reads 'The Osborn.'

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 11 - Oct 12
Total with taxes and fees
The Osthoff Resort
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.
A hotel with a modern design, featuring a prominent tower with the hotel name, a covered entrance, and a well-maintained lawn.

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.
$84 nightly
$95 total
Nov 3 - Nov 4
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.
A reception area with a wooden reception desk, a digital display, and a refrigerator stocked with beverages.
A bar area with wooden bar stools and a well-stocked liquor shelf.
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.
$125 nightly
$142 total
Nov 1 - Nov 2
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 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 hotel room with a bed, a desk with a sink, a chair, a small table, and a window with curtains.
A reception area with two desks, a TV, and orange chairs.

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
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 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.

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
Downtown Sheboygan
$133 nightly
$151 total
Nov 5 - Nov 6
Total with taxes and fees
Grandstay Residential Suites Hotel - 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 painting on the wall.
A hotel dining area with tables, chairs, a reception desk, and a ceiling fan.
A hotel room with a bed, a sofa, a desk, and a television.

Quality Inn Sheboygan North I-43

Quality Inn Sheboygan North I-43
Sheboygan
$80 nightly
$91 total
Nov 1 - Nov 2
Total with taxes and fees
Quality Inn Sheboygan North I-43
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.
An indoor swimming pool with clear water, tiled floor, and safety railings.

Comfort Inn & Suites Sheboygan I-43

Comfort Inn & Suites Sheboygan I-43
Sheboygan
$84 nightly
$95 total
Nov 3 - Nov 4
Total with taxes and fees
Comfort Inn & Suites Sheboygan I-43
An indoor swimming pool with clear blue water, tiled walls, and large windows offering a view of a field.
A reception area with two counters, a marble wall, an ATM, 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.
A bar area with a long counter, multiple stools, and a selection of beverages.

The Oasis Hotel & Bar

The Oasis Hotel & Bar
Sheboygan Falls
$65 nightly
$72 total
Nov 3 - Nov 4
Total with taxes and fees
The Oasis Hotel & Bar
An indoor swimming pool with lounge chairs and tables, a clear blue pool, and a high ceiling with visible structural beams.
A conference room with a long table, six chairs, and a wooden accent wall.
A hotel room with two beds, a desk, a chair, a TV, and an air conditioning unit.
A reception area with a wooden reception desk, a flat-screen TV, and a seating area with two chairs and a small table.

Wingate by Wyndham Sheboygan

Wingate by Wyndham Sheboygan
Downtown Sheboygan
$85 nightly
$97 total
Nov 1 - Nov 2
Total with taxes and fees
Wingate by Wyndham Sheboygan
An outdoor patio area with tables and chairs, string lights, and a view of the building in the background.
A buffet counter with a coffee machine, a display case with food, and a digital menu board.
A multi-story hotel with a modern design, featuring a covered outdoor seating area and a visible fire feature.
An indoor swimming pool with a geometric ceiling design, a seating area with chairs, and a view of the outdoors through large windows.

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 modern hotel entrance with a curved canopy, multiple floors, and a prominent sign.
A swimming pool with a lifeguard sign, lounge chairs, and a view of the outdoors.
A modern restaurant with wooden accents, white tiled walls, and yellow chairs.
An outdoor patio with stone walls, a fire feature, and seating.

Fairfield Inn & Suites by Marriott Sheboygan

Fairfield Inn & Suites by Marriott Sheboygan
Sheboygan
$125 nightly
$142 total
Nov 1 - Nov 2
Total with taxes and fees
Fairfield Inn & Suites by Marriott Sheboygan
An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled deck.
A hotel room with a flat-screen TV, a desk with a chair, a bed, a sofa, and a large window with curtains.
A reception area with a Baymont Inn & Suites sign, a reception desk, a small round table, and a decorative wreath.
A breakfast area with wooden tables and chairs, a coffee station, and a wall-mounted TV.

Baymont by Wyndham Plymouth

Baymont by Wyndham Plymouth
Plymouth
$125 nightly
$142 total
Oct 25 - Oct 26
Total with taxes and fees
Baymont by Wyndham Plymouth
A hotel with a curved facade, illuminated signage, and snow-covered surroundings.
Two people sitting on a couch facing a fireplace with a fruit platter on the table.
A spa area with a green heated floor, a ceiling with a cloud mural, and two relaxation chairs on either side.
A cozy living room with a fireplace, leather furniture, and a chandelier.

Inn On Woodlake

Inn On Woodlake
Kohler
$229 nightly
$253 total
Nov 1 - Nov 2
Total with taxes and fees
Inn On Woodlake
View all properties

Hotels with pools and hot tubs in 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 painting on the wall.
A hotel dining area with tables, chairs, a reception desk, and a ceiling fan.
A hotel room with a bed, a sofa, a desk, and a television.

Quality Inn Sheboygan North I-43

Quality Inn Sheboygan North I-43
Sheboygan
$80 nightly
$91 total
Nov 1 - Nov 2
Total with taxes and fees
Quality Inn Sheboygan North I-43
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.
An indoor swimming pool with clear water, tiled floor, and safety railings.

Comfort Inn & Suites Sheboygan I-43

Comfort Inn & Suites Sheboygan I-43
Sheboygan
$84 nightly
$95 total
Nov 3 - Nov 4
Total with taxes and fees
Comfort Inn & Suites Sheboygan I-43
An indoor swimming pool with clear blue water, tiled walls, and large windows offering a view of a field.
A reception area with two counters, a marble wall, an ATM, 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.
A bar area with a long counter, multiple stools, and a selection of beverages.

The Oasis Hotel & Bar

The Oasis Hotel & Bar
Sheboygan Falls
$65 nightly
$72 total
Nov 3 - Nov 4
Total with taxes and fees
The Oasis Hotel & Bar
An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled deck.
A hotel room with a flat-screen TV, a desk with a chair, a bed, a sofa, and a large window with curtains.
A reception area with a Baymont Inn & Suites sign, a reception desk, a small round table, and a decorative wreath.
A breakfast area with wooden tables and chairs, a coffee station, and a wall-mounted TV.

Baymont by Wyndham Plymouth

Baymont by Wyndham Plymouth
Plymouth
$125 nightly
$142 total
Oct 25 - Oct 26
Total with taxes and fees
Baymont by Wyndham Plymouth
A spacious atrium with a grand chandelier, multiple balconies, and large windows allowing natural light.
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.
A large, white building with a symmetrical facade and multiple balconies.

Blue Harbor Resort and Conference Center

Blue Harbor Resort and Conference Center
Sheboygan
$207 nightly
$235 total
Oct 7 - Oct 8
Total with taxes and fees
Blue Harbor Resort and Conference Center
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.
A spacious hotel lobby with a central kitchen area, a staircase, and a seating area with a sofa and a small table.

AmericInn by Wyndham Plymouth

AmericInn by Wyndham Plymouth
Plymouth
$101 nightly
$115 total
Nov 1 - Nov 2
Total with taxes and fees
AmericInn by Wyndham Plymouth
An indoor swimming pool with clear water, wooden walls, and a tiled floor.
A garden with a bench, a tree, and a view of the water.
A modern living room with a grey sofa, a wooden coffee table, and a dining area with a wooden table and chairs.
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
A view from a window overlooking a coastal area with a pathway leading to a building with a balcony.
A living room with a view of the sea, a sofa, a wooden table, and a painting on the wall.
A restaurant with wooden tables and chairs, large windows with a view of the sea, and hanging pendant lights.
A lobby with a wooden staircase, a reception desk, and a seating area with a sofa and chairs.

Lighthouse Inn

Lighthouse Inn
Two Rivers
$105 nightly
$119 total
Nov 1 - Nov 2
Total with taxes and fees
Lighthouse Inn
A hotel room with a bed, a desk with a chair, a television, a mirror, and a small table.
A modern lobby with a grey sofa, armchairs, and a large ship's wheel on the wall.
A hotel room with two beds, a desk, a TV, and a dresser.
A spacious indoor dining area with multiple tables and chairs, large windows offering views of the outdoors, and pendant lighting fixtures.

The Inn on Maritime Bay, an Ascend Collection Hotel

The Inn on Maritime Bay, an Ascend Collection Hotel
Manitowoc
$118 nightly
$134 total
Nov 1 - Nov 2
Total with taxes and fees
The Inn on Maritime Bay, an Ascend Collection Hotel
A hotel lobby with a glass door leading to a pool area.
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.
A modern hotel lobby with a high ceiling, a zebra-patterned carpet, and a glass partition with a view of the lobby area.

Holiday Inn Manitowoc by IHG

Holiday Inn Manitowoc by IHG
Manitowoc
$93 nightly
$106 total
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Manitowoc by IHG
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

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

8/10 Good
"Location was disappointing. We were driving everywhere for sightseeing and restaurants."
Barbara 2-night trip
Posted 7 hours ago
Grandstay Residential Suites Hotel - Sheboygan
Quality Inn Sheboygan North I-43

Quality Inn Sheboygan North I-43

8/10 Good
"The room was great. When going into hot tube it was hard to have a conversation with my partner cause kids where being so loud. The staff did nothing"
Sarah 1-night trip
Posted 7 hours ago
Quality Inn Sheboygan North I-43
La Quinta Inn by Wyndham Sheboygan

La Quinta Inn by Wyndham Sheboygan

8/10 Good
"Room was clean. Smelled like the perfume strippers wear. Staff was friendly and helpful. Sign said rooms not made up on Friday and Sunday unless requested. We stayed over and our room was not made up on Saturday, but trash removed. VERY convenient to Road America. Don’t know if restaurants are near, but there is a McDonald’s very close. Would stay here again."
jeff 3-night trip
Posted 1 day ago
La Quinta Inn by Wyndham Sheboygan
Wingate by Wyndham Sheboygan

Wingate by Wyndham Sheboygan

10/10 Excellent
"Clean room"
Stefani 1-night trip
Posted 2 days ago
Wingate by Wyndham Sheboygan
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 8 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 9 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 2 weeks 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 $91 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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