Sheboygan Vacation Rentals

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Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Sheboygan vacation rentals

Cabin, Lake View | Beach

Tiki Beach Campground

Tiki Beach Campground
3.0 star property
Campbellsport
10.0 out of 10, Exceptional, (1 review)
"Beautiful"
United States
Angela
The price is ￥15,705
￥16,568 total
includes taxes & fees
Apr 21 - Apr 22
Tiki Beach Campground
Lobby

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,027 reviews)
"Room was clean, staff was nice. The breakfast was pretty darn good. "
United States
andrea
The price is ￥22,665
￥25,724 total
includes taxes & fees
Apr 21 - Apr 22
Grandstay Residential Suites Hotel - Sheboygan
Bar (on property)

Victorian Inn Elkhart Lake Wisconsin

Victorian Inn Elkhart Lake Wisconsin
4.0 star property
Elkhart Lake
8.8 out of 10, Excellent, (3 reviews)
"Perfect location, great amenities."
United States
Deirdre
The price is ￥19,277
￥101,734 total
includes taxes & fees
Apr 21 - Apr 22
Victorian Inn Elkhart Lake Wisconsin
Interior

Gleason's Chouse

Gleason's Chouse
Campbellsport
10.0 out of 10, Exceptional, (41 reviews)
"Incredibly decorated home. Loved staying here. "
United States
Mike L.
The price is ￥21,416
￥30,628 total
includes taxes & fees
Apr 21 - Apr 22
Gleason's Chouse
Living area

Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.

Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
Ellis Historical District
9.6 out of 10, Exceptional, (12 reviews)
"A warm and cozy place to stay. Beautifully decorated and friendly hosts. Would stay again anytime we’re in Sheboygan."
United States
Rebecca S.
The price is ￥18,244
￥24,309 total
includes taxes & fees
Apr 22 - Apr 23
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
Smart TV

3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown

3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
Sheboygan
10.0 out of 10, Exceptional, (14 reviews)
"Very nice,had everything you need. Nicely decorated.. close to town and parks"
United States
Dennis B.
The price is ￥12,533
￥25,929 total
includes taxes & fees
Apr 27 - Apr 28
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
Living area

2nd floor loft near the lake!

2nd floor loft near the lake!
Manitowoc
9.8 out of 10, Exceptional, (17 reviews)
"Very clean, and tastefully decorated…would rent again:)"
United States
Kim B.
The price is ￥20,703
￥35,563 total
includes taxes & fees
Apr 21 - Apr 22
2nd floor loft near the lake!
Children's area

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Oostburg
10.0 out of 10, Exceptional, (126 reviews)
"Welcoming and accommodating host, very clean and cozy cottage, amazing fireplace "
United States
Cade R.
The price is ￥19,989
￥24,436 total
includes taxes & fees
Apr 28 - Apr 29
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
1 bedroom, WiFi

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Ellis Historical District
9.8 out of 10, Exceptional, (25 reviews)
"Great place! Nice location and very comfortable. "
United States
Jana F.
The price is ￥15,071
￥20,707 total
includes taxes & fees
Apr 23 - Apr 24
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Interior

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Sheboygan
10.0 out of 10, Exceptional, (4 reviews)
"Very clean and good location; nice place for our dog; we would definitely stay again if the opportunity presents itself."
United States
Stephanie K.
The price is ￥18,085
￥31,330 total
includes taxes & fees
Apr 21 - Apr 22
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Dining

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Downtown Sheboygan
10.0 out of 10, Exceptional, (13 reviews)
"Super cute place with great amenities. I even got to park my car in the garage! We enjoyed our stay here!"
United States
Carolyn W.
The price is ￥15,071
￥39,614 total
includes taxes & fees
May 4 - May 5
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Beach nearby, sun loungers, beach towels

No Cleaning Fee. King Bed. Cedar soaking Hot Tub, 5min walk to Beach

No Cleaning Fee. King Bed. Cedar soaking Hot Tub, 5min walk to Beach
Two Rivers
10.0 out of 10, Exceptional, (22 reviews)
"Amazing place with exceptional hospitality. Every detail has been thoughtfully considered, from the amenities to the overall comfort. The design is beautiful, and the outdoor space offers wonderfully relaxing vibes. We’d definitely love to return—thank you for hosting us!"
United States
Aleks M.
The price is ￥30,935
￥39,793 total
includes taxes & fees
Apr 21 - Apr 22
No Cleaning Fee. King Bed. Cedar soaking Hot Tub, 5min walk to Beach
Exterior

The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (59 reviews)
"Great spot, super close to town (and the always great Off The Rail cafe). Clean and quiet. Used as a base for track time at Road America."
United States
Scott G.
The price is ￥31,569
￥43,013 total
includes taxes & fees
Apr 21 - Apr 22
The Esker Ridge Chalet, Pristine Elkhart Solitude
Bar (on property)

First Floor Pet Friendly Queen Suite with Single Pull-out

First Floor Pet Friendly Queen Suite with Single Pull-out
Elkhart Lake
10.0 out of 10, Exceptional, (2 reviews)
"So convenient to all things Elkhart Lake. Great accommodations and host. Would highly recommend!"
United States
Brenda H.
The price is ￥36,551
￥61,843 total
includes taxes & fees
Apr 21 - Apr 22
First Floor Pet Friendly Queen Suite with Single Pull-out
Apartment (2 Bedrooms) | Front of property

Modern South Pier Condo on Sheboygan River!

Modern South Pier Condo on Sheboygan River!
4.0 star property
Sheboygan
The price is ￥27,127
￥63,790 total
includes taxes & fees
May 10 - May 11
Modern South Pier Condo on Sheboygan River!
Interior

Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth

Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
Plymouth
9.6 out of 10, Exceptional, (10 reviews)
"Great property! Close to many great places. Property was very kid and adult friendly. Great time with family. We'll be back again. "
United States
Andrew M.
The price is ￥30,411
￥91,164 total
includes taxes & fees
Apr 21 - Apr 22
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
Property grounds

New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
Two Rivers
10.0 out of 10, Exceptional, (34 reviews)
"The property was very nice, clean, and comfortable! The hosts were very kind and available if you needed them. A great place to stay if youre in the area!"
United States
Tara F.
The price is ￥15,705
￥38,713 total
includes taxes & fees
Apr 24 - Apr 25
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
Fridge, microwave, oven, stovetop

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Sheboygan
10.0 out of 10, Exceptional, (41 reviews)
"We absolutely loved our stay. Everything was so well stocked and comfortable. Perfect location near the lake. Between the fenced in yard for the dog and the little play area for the kids, it couldn’t have worked out better."
United States
Jean S.
The price is ￥21,416
￥64,821 total
includes taxes & fees
Apr 21 - Apr 22
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
3 bedrooms, desk, iron/ironing board, travel crib

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Sheboygan
9.4 out of 10, Exceptional, (11 reviews)
"Coastal Comfort was very clean, pleasantly decorated and comfortable. It is within driving distance to the lake as well as restaurants in Sheboygan. Perfect stay for the two of us. "
United States
Kim K.
The price is ￥19,703
￥33,348 total
includes taxes & fees
Apr 26 - Apr 27
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Exterior

Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.6 out of 10, Exceptional, (4 reviews)
"We had a great stay here during the boat races. The host was so nice and left us local cheese & beer to welcome us to the house/city. We would definitely stay here again!"
United States
MELISSA C.
The price is ￥21,892
￥57,258 total
includes taxes & fees
May 11 - May 12
Logan Ave Holiday House - Upper
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

Comfort Inn & Suites Sheboygan I-43

Comfort Inn & Suites Sheboygan I-43

10/10 Excellent
"Great place to bring kids. "
yufeng 1-night trip
Posted 8 hours ago
Comfort Inn & Suites Sheboygan I-43

Find out more about Sheboygan

Search for holiday rentals in Sheboygan on Expedia! You can easily find your home rentals, villas, holiday apartments in Sheboygan using one of the methods below:

  • View our selection of featured holiday rentals in Sheboygan
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Look no further and take a look at our great range of rental properties in Sheboygan!

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Frequently asked questions

Can I find a vacation rental in Sheboygan?

Yes, we offer vacation rentals in Sheboygan close to John Michael Kohler Arts Center, or you can go with a more remote option if you want a relaxing stay. Visitors to Sheboygan speak positively about the popular beaches and top-notch restaurants in this destination. Leave some time to check out the marina and museums during your trip.

What are some of the best vacation home rentals in Sheboygan?

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!: This Sheboygan vacation home rental is located on a lake and has a fireplace, a balcony, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games. Our travelers also rate REMODELED HOME ON LAKE MICHIGAN as a favorite home for rent in Sheboygan.

How many vacation rentals will I find in Sheboygan?

Choose from 98 Expedia vacation rentals in Sheboygan for a memorable vacation.

What’s there to see and do in Sheboygan?

Enjoy the outdoors at Lake Michigan and North Side Municipal Beach, or simply take in cultural attractions like John Michael Kohler Arts Center and Sheboygan County Historical Museum. While here, Stefanie H. Weill Center for the Performing Arts and Blue Harbor Resort & Conference Center Water Park are other places worth a visit.

What’s a vacation rental in Sheboygan like?

A vacation rental is a private property where you can stay for a long or short time in Sheboygan. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family getaway.