Sheboygan Vacation Rentals

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Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Sheboygan vacation rentals

Lobby

Aparthotel in Downtown Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
8.6 out of 10, Excellent, (1,019 reviews)
"Great start!! Will be back!"
United States
Venir
$109 nightly
The price is $124
Jan 28 - Jan 29
Total with taxes and fees
Grandstay Residential Suites Hotel - Sheboygan
House (2 Bedrooms) | Interior

Cottage in Sheboygan

Large Backyard, Walk to Hospital: Sheboygan Abode!
3.0 star property
$364 nightly
The price is $409
Jan 28 - Jan 29
Total with taxes and fees
Large Backyard, Walk to Hospital: Sheboygan Abode!
Fridge, microwave, oven, stovetop

Apartment in Sheboygan

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan
9.8 out of 10, Exceptional, (12 reviews)
"We stayed in the upstairs last year and loved it. The downstairs did not disappoint either! Very clean, welcoming, and convenient location. We look forward to staying again next year. "
United States
MELISSA C.
$263 nightly
The price is $298
Feb 1 - Feb 2
Total with taxes and fees
Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan
Interior

Apartment in Sheboygan

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
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.
$150 nightly
The price is $170
Jan 28 - Jan 29
Total with taxes and fees
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
1 bedroom, WiFi

Apartment in Ellis Historical District

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
9.8 out of 10, Exceptional, (24 reviews)
"Great place! Nice location and very comfortable. "
United States
Jana F.
$115 nightly
The price is $131
Jan 30 - Jan 31
Total with taxes and fees
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Smart TV

Vacation Home in Sheboygan

3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
10.0 out of 10, Exceptional, (13 reviews)
"Great place to stay and even better hosts’. The house is conveniently located to everything we wanted to explore and was a great place to unwind after a long day. The host was very helpful and made sure we were settled in and having a good time. Would love to come back soon! "
United States
Riley W.
$118 nightly
The price is $134
Jan 28 - Jan 29
Total with taxes and fees
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
Property grounds

Vacation Home in Two Rivers

New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
10.0 out of 10, Exceptional, (33 reviews)
"Had a great weekend getaway with the family. "
United States
Joe Z.
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
Dining

Apartment in Downtown Sheboygan

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
10.0 out of 10, Exceptional, (11 reviews)
"The flat is gorgeous and in a fantastic location. "
United States
Sarah G.
$208 nightly
The price is $236
Feb 2 - Feb 3
Total with taxes and fees
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
3 bedrooms, desk, iron/ironing board, travel crib

Apartment in Sheboygan

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
9.2 out of 10, Wonderful, (10 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.
$141 nightly
The price is $160
Feb 1 - Feb 2
Total with taxes and fees
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
3 bedrooms, iron/ironing board, travel crib, WiFi

Apartment in Sheboygan

Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
10.0 out of 10, Exceptional, (1 review)
"In town for family celebration. This was a convenient location to my parent’s home! Thanks!"
United States
Shelly E.
$141 nightly
The price is $160
Jan 28 - Jan 29
Total with taxes and fees
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Children's area

Vacation Home in Oostburg

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
10.0 out of 10, Exceptional, (119 reviews)
"Lovely place and quiet"
United States
grandma d.
$150 nightly
The price is $158
Feb 2 - Feb 3
Total with taxes and fees
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Living area

Apartment in Manitowoc

2nd floor loft near the lake!
9.8 out of 10, Exceptional, (15 reviews)
"Very clean, and tastefully decorated…would rent again:)"
United States
Kim B.
$199 nightly
The price is $225
Jan 28 - Jan 29
Total with taxes and fees
2nd floor loft near the lake!
Exterior

Apartment in Sheboygan

Logan Ave Holiday House - Upper
9.4 out of 10, Exceptional, (3 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.
$260 nightly
The price is $295
Jan 28 - Jan 29
Total with taxes and fees
Logan Ave Holiday House - Upper
Dining

Vacation Home in Sheboygan

Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
10.0 out of 10, Exceptional, (6 reviews)
"4 forever friends getaway. Relaxation, eats and drinks with a little antique and thrift shopping"
United States
Stacy P.
$163 nightly
The price is $185
Jan 28 - Jan 29
Total with taxes and fees
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Interior

Apartment in Sheboygan

*NEW* Sleeps 8 & Spacious!
10.0 out of 10, Exceptional, (28 reviews)
"Great location! Roomy, close to everything, very nice inside, clean, always found parking."
United States
Beth D.
*NEW* Sleeps 8 & Spacious!
Fridge, microwave, oven, stovetop

Vacation Home in Sheboygan

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
10.0 out of 10, Exceptional, (40 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.
$332 nightly
The price is $377
Feb 1 - Feb 2
Total with taxes and fees
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Living area

Vacation Home in Ellis Historical District

Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
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.
$135 nightly
The price is $153
Jan 28 - Jan 29
Total with taxes and fees
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
Interior

Vacation Home in Two Rivers

Beach Walk Home with Hot Tub and Fire Pit
$372 nightly
The price is $429
Jan 28 - Jan 29
Total with taxes and fees
Beach Walk Home with Hot Tub and Fire Pit
Living area

Apartment in Brillion

Luxury Suites #3
10.0 out of 10, Exceptional, (1 review)
"Apartments were clean with easy access. Centrally located entertainment room was enjoyed by my granddaughter with claw machines, games, and TV. It is a newer property and still needs a few touches, like wall decor to soften the echoes. A bench outside the individual rentsls would be nice for seating, but there's a great area out back with chairs and heating if needed. "
United States
Debby
$272 nightly
The price is $298
Jan 28 - Jan 29
Total with taxes and fees
Luxury Suites #3
Smart TV

Vacation Home in Sheboygan

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
10.0 out of 10, Exceptional, (23 reviews)
"Wonderfully close to the lake. Sad there was no off street parking."
United States
Lucas T.
$316 nightly
The price is $359
Jan 28 - Jan 29
Total with taxes and fees
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
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

Beach front luxury spacious villa !

Beach front luxury spacious villa !

10/10 Excellent
"The host was very nice and responsive. House was clean. "
Candace C. 2-night trip
Posted 2 days ago
Beach front luxury spacious villa !

Find out more about Sheboygan

Everything you need to know about Sheboygan vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sheboygan vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sheboygan vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sheboygan vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sheboygan. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Sheboygan in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $124 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sheboygan rentals

At Expedia, we put the best Sheboygan vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Sheboygan rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sheboygan vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sheboygan. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Sheboygan?

Yes, we offer vacation rentals in Sheboygan close to Blue Harbor Resort & Conference Center Water Park, 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?

Lake Michigan Home with gorgeous views, great spot for family or golf retreat: This Sheboygan vacation home rental is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Our travelers also rate Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX as a favorite home for rent in Sheboygan.

How many vacation rentals will I find in Sheboygan?

Choose from 95 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 Bookworm Gardens, or simply take in cultural attractions like John Michael Kohler Arts Center and Stefanie H. Weill Center for the Performing Arts. While here, Blue Harbor Resort & Conference Center Water Park and Kohler Park Dunes State Natural Area 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.