Sheboygan, WI Cottage Rentals from $476

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Our top choices for Sheboygan cottages

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

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

Two Rivers

$435 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

2. Charming cottage on Lake Winnebago

Neenah

Joe M.

$414 nightly

Nov 16 - Nov 17

Total with taxes and fees

A wooden deck with a glass railing overlooking a snowy landscape with trees.

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

Hubertus

$732 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

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

Fond du Lac

"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...

Dani H.

$1,607 nightly

Nov 19 - Nov 20

Total with taxes and fees

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

Fond du Lac

"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)...

Magen S.

$798 nightly

Nov 19 - Nov 20

Total with taxes and fees

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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.

See all hotels in Sheboygan

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

Top reviews in Sheboygan

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

The Rochester Inn, A Historic Hotel

Sheboygan Falls

10/10 Excellent

Anonymous traveler

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

Kress Inn, an Ascend Collection Hotel

De Pere

10/10 Excellent

Brooke

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

Fairfield Inn & Suites by Marriott Sheboygan

Sheboygan

10/10 Excellent

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...

Jenny

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

Inn On Woodlake

Kohler

10/10 Excellent

Dennis

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

Home2 Suites by Hilton Appleton

Appleton

10/10 Excellent

Rene

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

Hotel Retlaw, Trademark Collection by Wyndham

Fond du Lac

10/10 Excellent

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...

Ward

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

CopperLeaf Hotel BW Premier Collection

Appleton

10/10 Excellent

Lisa

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

Hampton Inn Appleton-Fox River Mall Area

Appleton

10/10 Excellent

Valerie

An outdoor patio area with multiple tables and chairs, ceiling fans, and a view of the outdoor space.

Best Western Premier Bridgewood Resort Hotel

Neenah

10/10 Excellent

Anonymous traveler

A view from a balcony overlooking a snow-covered landscape with a road, trees, and a distant building.

Siebkens Resort

Elkhart Lake

10/10 Excellent

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!

Mary

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

The Osthoff Resort

Elkhart Lake

10/10 Excellent

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...

Robert

A patio with tables and chairs, a red umbrella, and a view of a body of water and buildings.

The Harborview on Lake Michigan, an Ascend Collection Hotel

Port Washington

10/10 Excellent

Tammy

A modern building with a brick facade and large windows.

Cobblestone Hotel & Suites - De Pere/Green Bay

De Pere

10/10 Excellent

Diane

A Holiday Inn Express hotel with a modern design, featuring a large entrance and a parking area.

Holiday Inn Express & Suites Green Bay East by IHG

Green Bay

10/10 Excellent

Jacqueline

Frequently Asked Questions

How much do cottages in Sheboygan cost?

Prices for cottages in Sheboygan range between $476 and $1,823 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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Sheboygan Vacation Rentals
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Search Sheboygan Cottages

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Sheboygan cottages

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

2. Charming cottage on Lake Winnebago

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

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

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

Sheboygan and related destinations

Top reviews in Sheboygan

The Rochester Inn, A Historic Hotel

10/10 Excellent

Frequently Asked Questions

How much do cottages in Sheboygan cost?

Why book your cottage in Sheboygan with Expedia?

How can I find cheap cottages in Sheboygan?

What is there to do in Sheboygan near my cottage?

Explore a world of travel with Expedia