A rocky shoreline with waves crashing against the rocks and a large weeping willow tree in the background.

Find Hotels with a Pool in Cleveland, WI

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Check availability on Cleveland Hotels with a Pool

Tonight
12 Aug - 13 Aug
Tomorrow
13 Aug - 14 Aug
This weekend
14 Aug - 16 Aug
Next weekend
21 Aug - 23 Aug

Our top choices for Cleveland hotels with a pool

Indoor pool
Free daily full breakfast
Pillowtop beds, in-room safe, desk, iron/ironing board
Hydromassage showerhead, free toiletries, hair dryer, towels

1. 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.
SAR 311
SAR 353 total
includes taxes & fees
13 Sep - 14 Sep
Quality Inn Sheboygan North I-43
Indoor pool
Bar (on property)
Down comforters, desk, soundproofing, iron/ironing board
Bar (on property)

2. AmericInn by Wyndham Manitowoc

AmericInn by Wyndham Manitowoc
Manitowoc
  • Indoor pool paradise with a children's pool and hot tub for aquatic fun in Manitowoc.
SAR 380
SAR 431 total
includes taxes & fees
23 Aug - 24 Aug
AmericInn by Wyndham Manitowoc
Indoor pool
Terrace/patio
Iron/ironing board, WiFi (free)
Free daily breakfast

3. 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.
SAR 520
SAR 591 total
includes taxes & fees
23 Aug - 24 Aug
Home2 Suites By Hilton Sheboygan
Indoor pool
Exterior
Exterior
Down comforters, in-room safe, desk, iron/ironing board

4. Holiday Inn Manitowoc by IHG

Holiday Inn Manitowoc by IHG
Manitowoc
  • Indoor oasis awaits with divine hot tub and pool for year-round swimming and relaxation.
SAR 357
SAR 405 total
includes taxes & fees
13 Sep - 14 Sep
Holiday Inn Manitowoc by IHG
Indoor pool, open 6:00 AM to 10:00 PM, sun loungers
Luxury Room, 1 King Bed | Premium bedding, desk, blackout drapes, WiFi (free)
Game room
Reception

5. The Oasis Hotel & Bar

The Oasis Hotel & Bar
Sheboygan Falls
  • Splash into serenity at this Lake Michigan hotel with year-round indoor pool and arcade fun.
SAR 289
SAR 319 total
includes taxes & fees
13 Sep - 14 Sep
The Oasis Hotel & Bar
Indoor pool
Room, 2 Double Beds, Non Smoking | Premium bedding, memory foam beds, in-room safe, desk
Dining
Lobby

6. Wingate by Wyndham Sheboygan

Wingate by Wyndham Sheboygan
Downtown Sheboygan
  • Dive into lakeside adventures with an indoor pool, arcade, and hiking trails nearby.
SAR 342
SAR 388 total
includes taxes & fees
13 Sep - 14 Sep
Wingate by Wyndham Sheboygan
Indoor pool
Desk, laptop workspace, blackout drapes, iron/ironing board
Property amenity
Free daily continental breakfast

7. The Inn on Maritime Bay, an Ascend Collection Hotel

The Inn on Maritime Bay, an Ascend Collection Hotel
Manitowoc
  • Splash into relaxation at this maritime hotel with an indoor pool oasis for all-weather fun.
SAR 476
SAR 540 total
includes taxes & fees
13 Sep - 14 Sep
The Inn on Maritime Bay, an Ascend Collection Hotel
Indoor pool
Free daily on-the-go breakfast
Exterior
Egyptian cotton sheets, premium bedding, pillowtop beds, desk

8. 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.
SAR 460
SAR 522 total
includes taxes & fees
1 Sep - 2 Sep
Grandstay Residential Suites Hotel - Sheboygan
Indoor pool
In-room safe, desk, iron/ironing board, cribs (surcharge)
Suite, 2 Queen Beds, Non Smoking | In-room safe, desk, iron/ironing board, cribs (surcharge)
Exterior

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.
SAR 338
SAR 384 total
includes taxes & fees
3 Sep - 4 Sep
Comfort Inn & Suites Sheboygan I-43
Indoor pool
Lobby sitting area
Coffee/tea maker, fridge, microwave
Front of property

10. Cobblestone Hotel & Suites - Two Rivers

Cobblestone Hotel & Suites - Two Rivers
Two Rivers
  • Luxurious indoor pool retreat beckons with year-round swimming and riverside relaxation in a clean, modern hotel setting.
SAR 319
SAR 378 total
includes taxes & fees
16 Aug - 17 Aug
Cobblestone Hotel & Suites - Two Rivers
View all properties

Choose what matters most at hotels with a pool in Cleveland

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Cleveland Hotel Reviews

Harbor Town, BW Signature Collection

Harbor Town, BW Signature Collection

8/10 Good
"Overnight stay. The place is a little older & shabby, but it was clean and wifi was good."
Kathy 1-night trip
Posted 3 hours ago
Harbor Town, BW Signature Collection
AmericInn by Wyndham Sheboygan

AmericInn by Wyndham Sheboygan

8/10 Good
"Very nice pool, breakfast, cookies and snacks. Helpful staff."
Gabriel 3-night trip
Posted 6 hours ago
AmericInn by Wyndham Sheboygan
The Inn on Maritime Bay, an Ascend Collection Hotel

The Inn on Maritime Bay, an Ascend Collection Hotel

8/10 Good
"Gorgeous location. Needs updates to physical plant."
Mary 1-night trip
Posted 1 day ago
The Inn on Maritime Bay, an Ascend Collection Hotel
AmericInn by Wyndham Manitowoc

AmericInn by Wyndham Manitowoc

10/10 Excellent
"Great breakfast. Nice staff and clean room."
Joyce 1-night trip
Posted 2 days ago
AmericInn by Wyndham Manitowoc
Holiday Inn Manitowoc by IHG

Holiday Inn Manitowoc by IHG

8/10 Good
"This hotel 15 years ago was probably great. It’s kind of worn out now."
Nancy 2-night trip
Posted 2 days ago
Holiday Inn Manitowoc by IHG
Quality Inn Sheboygan North I-43

Quality Inn Sheboygan North I-43

8/10 Good
"Breakfast was very crowded so we grabbed something and sat outside, juat a quick stay after a brewers game. Staff was very helpful with our late night checkin."
Lindsay 1-night trip
Posted 3 days ago
Quality Inn Sheboygan North I-43
The Osthoff Resort

The Osthoff Resort

10/10 Excellent
"Great family trip! Loved the multiple pools, the beach was perfect, bars/restaurants at the lake and pool! Perfect for families."
JESSICA HARAMIS 4-night trip
Posted 5 days ago
The Osthoff Resort

Frequently asked questions

What are some accommodations with pools in Cleveland?
Shoreline Serenity - 2 Private Acres: Vacation home, 1-minute walk from Lake Michigan. Offers complimentary wireless internet access, a pool, and kitchens. Insane luxury beachfront estate - complete with indoor pool, arcade and theater!: Hotel, 1-minute walk from Lake Michigan. Features a private beach, an indoor pool, and cooked-to-order. Lighthouse Inn: Hotel, 6-minute walk from Lake Michigan. Offers a snack bar/deli, an indoor pool, and continental. Harbor Town, BW Signature Collection: Aparthotel, 14-minute walk from Lake Michigan. Provides daily, an indoor pool, and free self parking. Watershed Hotel: Hotel, 7-minute walk from Lake Michigan. Features a sauna, an indoor pool, and daily.
What is there to see and do in Cleveland?
Explore places like Lake Michigan while you're in Cleveland. Make a point to visit attractions like North Side Municipal Beach and Bookworm Gardens.
When is the best time to book a hotel with a pool in Cleveland?
Taking into account the local weather in Cleveland is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Cleveland are January, March, February, and October, with each month seeing an average of 7 inches of snowfall.