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Check prices for these dates, December 14 – 15, 2026

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Our top choices for Sheboygan cottages

1. 1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

A suburban street with houses, a gas station, and a clear sky.

Location: Two Rivers
Price: $435 nightly, $490 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Sheboygan cottages

2. Charming cottage on Lake Winnebago

A brick house with a chimney, a front porch, and a well-maintained garden.

Location: Neenah
Guest rating: 10/10 (Exceptional, 60 reviews)
Price: $414 nightly, $476 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Sheboygan cottages
Review: Great rental, beautiful lakefront!, by Sara D.

3. Eclectic Hubertus Home w/ Game Room & Fire Pit!

A wooden deck with outdoor seating, large windows, and a view of trees.

Location: Hubertus
Price: $732 nightly, $772 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Sheboygan cottages

4. Pontoon Included with Cottage! Boat or JetSki Lake Winnebago! Package Deal!

A grassy area with a house, a pond, and a building with a textured exterior.

Location: Fond du Lac
Guest rating: 10/10 (Exceptional, 1 review)
Price: $1,599 nightly, $1,815 total, Nov 21 - Nov 22, Total with taxes and fees, for Our top choices for Sheboygan cottages
Review: "My husband and I just had the absolute best stay at this amazing little cottage on the Fond du Lac River! If you are looking for a perfect getaway just down the river from Lake Winnebago, this is absolutely the place to book.The cottage itself is incredibly cute, beautifully decorated, and was spotless when we arrived. The host has thought of everything to make it feel like a home away from home. We spent our days making full use of the kayaks (provided by host at no charge) and fishing right..., by Dani H.

5. Boat or WaveRunner Rentals available next door! Relax or Explore Lake Winnebago!

Location: Fond du Lac
Guest rating: 10/10 (Exceptional, 1 review)
Price: $798 nightly, $906 total, Nov 21 - Nov 22, Total with taxes and fees, for Our top choices for Sheboygan cottages
Review: "Excellent stay! We couldn’t be happier with our time at this cottage. We enjoyed using their four complimentary kayaks (they had life jackets and paddles for us), had a fire at night (host supplied free chopped firewood), grilled out burgers on the grill, and rented a pontoon boat and wave runner (Lake Winnebago Boat & WaveRunner Rentals is next door. The host (Brad) who owns this cottage also owns the boat rental place next door). We even did some fishing (there is a bait shop also next door)..., by Magen S.

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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Sheboygan and related destinations

Stroll the pristine Lake Michigan shoreline where surfers catch surprisingly good waves and locals grill world-class bratwurst. The Kohler-Andrae State Park offers sandy dunes and boardwalk trails, while downtown's art scene thrives in renovated brick buildings from the 1920s.

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

Top reviews in Sheboygan

The Rochester Inn, A Historic Hotel

A two-story white building with green shutters, a front porch, and a staircase leading to the upper floor.

Location: Sheboygan Falls
Review: A quaint, hidden gem! A beautiful room, ultra comfortable mattress, soft cozy bedding, unique amenities, and whirlpool tub. The almond crusted french toast for breakfast was off the charts! Located off the beaten path and worth seeking out. The inn, room, amenities, service and breakfast are memorable. Hope to visit again some day!, by Anonymous traveler, January 2, 2021, rated 10/10 Excellent

Kress Inn, an Ascend Collection Hotel

A large brick building with a central entrance, surrounded by well-maintained lawns and a clear sky.

Location: De Pere
Review: The room was stunning! Beautiful tile shower, reclining chair, two sink & mirror areas for getting ready, good breakfast, a wrap around writing desk, Starbucks coffee in room & guest passes to the YMCA. Cruiser bikes available for guests. Nice neighborhood for a stroll. Absolutely wonderful hotel, I highly recommend! ⭐️⭐️⭐️⭐️⭐️, by Brooke, June 30, 2023, rated 10/10 Excellent

The American Club

A large brick building with a prominent American Club sign, surrounded by lush greenery and a well-maintained lawn.

Location: Kohler
Review: Love this place. Everything is perfect. Will be back again soon., by Anna, December 14, 2023, rated 10/10 Excellent

Fairfield Inn & Suites by Marriott Sheboygan

A modern hotel entrance with a curved canopy, multiple floors, and a prominent sign.

Location: Sheboygan
Review: My 6 year old daughter and I were taking our first "mother-daughter" vacation to Sheboygan for a few days. We were originally reserved to stay at a nearby hotel. That experience was a nightmare (extremely dirty hotel room, "upgraded" to another dirty room, terrible customer service, etc.) and it looked like I was going to have to cancel our trip and my daughter was very upset. At the last minute, there was an opening at Fairfield Inn that my husband was able to reserve for us. He had been..., by Jenny, September 6, 2021, rated 10/10 Excellent

Home2 Suites by Hilton Appleton

A modern hotel building with a sign reading "HOME 2 SUITES BY HILTON".

Location: Appleton
Review: Best hotel room ever .... Keep up the great work... Very pleased....., by Rene, December 30, 2020, rated 10/10 Excellent

Inn On Woodlake

A hotel with a curved facade, illuminated signage, and snow-covered surroundings.

Location: Kohler
Review: Nice hotel. Great change of pace from the big chain hotels. Especially appreciated the access to The Sports Core for a workout., by Dennis, April 19, 2024, rated 10/10 Excellent

CopperLeaf Hotel BW Premier Collection

A multi-story building with a series of vertical banners displaying the name "Copper Leaf".

Location: Appleton
Review: Great night at the Copper Leaf. Cozy room with great beds and we enjoyed a drink and sharable at Rye…the restaurant attached to the hotel., by Lisa, July 12, 2025, rated 10/10 Excellent

Hotel Retlaw, Trademark Collection by Wyndham

A hotel entrance with a sign reading "HOTEL RETLAW".

Location: Fond du Lac
Review: Historic hotel fully restored with black marble floors, comfortable room & bed, comfortable furniture, free parking, overhead rain forest type bathroom shower, immaculately clean (room, hallways, elevator & lobby), friendly staff & rich flair of the past hotel glory from 1913. Shall stay here again. A delightful change & surprize from todays chain hotels. My wife & I took a unknown risk to stay @ Retlaw for tge first time and were rewarded with a very fine, enjoyable, relaxing & interesting..., by Ward, August 21, 2024, rated 10/10 Excellent

Hampton Inn Appleton-Fox River Mall Area

A Hampton Inn by Hilton building with a large sign, a parking lot, and a well-maintained lawn.

Location: Appleton
Review: Great rooms and very friendly staff, by Valerie, November 10, 2026, rated 10/10 Excellent

Best Western Premier Bridgewood Resort Hotel

A modern building with a sign for Batley's Grill & Bar, featuring a prominent entrance and awnings.

Location: Neenah
Review: The staff were welcoming and efficient at getting me checked in, and they had a tray of lots of different types of cookies available for a welcome snack, as well as coffee and tea in the lobby, which was very welcome after a long day traveling., by Anonymous traveler, March 18, 2015, rated 10/10 Excellent

Siebkens Resort

A building with a green awning labeled "Siebkens" and a brick facade.

Location: Elkhart Lake
Review: We wanted to take a night off in the country away from the Chicago area and our favorite two hour away place is Elkhart Lake, WI. We were upgraded to a 2 bedroom condo due to an issue in the reserved room. The condo had a fireplace, kitchen, a tremendous view of the lake, it was outstanding! We didn't expect the upgrade but the staff was so accommodating, what a delightful stay at Siebken's in Elkhart Lake, thank you!, by Mary, March 24, 2018, rated 10/10 Excellent

The Osthoff Resort

An aerial view of a residential area with a large central building, a lake, and surrounding greenery.

Location: Elkhart Lake
Review: Had some mechanical issues on a hot first day. A/C compressor was not starting on each cycle. Whirlpool would not shut off. Tried for an hour did not want to bother other guests but finally got it shut off. Minor maintenance issue. We had to leave early and return late from a conference about 70 miles away. Other guests would hog all the parking places on our side every day and had to park on opposite side of resort and walk around late at night after a long day. It is a large resort and a long..., by Robert, July 27, 2015, rated 10/10 Excellent

The Harborview on Lake Michigan, an Ascend Collection Hotel

A waterfront patio with outdoor seating, a railing, and a view of the water.

Location: Port Washington
Review: Always stay at the Harborview when in Port Washington. We’ve not been disappointed!, by Tammy, October 5, 2024, rated 10/10 Excellent

Holiday Inn Appleton by IHG

A Holiday Inn hotel with a brick facade, a covered entrance, and a landscaped area with small trees.

Location: Appleton
Review: Everything was terrific, really nice rooms, friendly staff, beautiful pool and hot tub. Coffee was free but other than that there is no basic free breakfast. Kids eat free with a full price adult entree., by Anonymous traveler, July 1, 2019, rated 10/10 Excellent

Frequently Asked Questions

How much do cottages in Sheboygan cost?

Prices for cottages in Sheboygan range between $476 and $1,814 per night. No matter your budget, you'll find the ideal place to get in touch with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

Why book your cottage in Sheboygan with Expedia?

We think that vacays should be a breeze, so if you're after cottages in Sheboygan at a great price, Expedia has got you covered. Save those pennies and select a cheap option surrounded by nature, or book an upmarket cottage to pamper your loved ones.

How can I find cheap cottages in Sheboygan?

The easiest way to locate cheap cottages in Sheboygan is with Expedia's useful filter tool. Refine your search results by star rating, amenities and budget to snag awesome rates in just a few keystrokes.

What is there to do in Sheboygan near my cottage?

You'll find loads of terrific things to see and do in Sheboygan. Don't miss major attractions like Sheboygan County Historical Museum, Blue Harbor Resort & Conference Center Water Park and Whistling Straits Golf Course. John Michael Kohler Arts Center, Stefanie H. Weill Center for the Performing Arts and Above & Beyond Children's Museum are also visitor favorites.

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