Photo by John Sukowaty

Sheboygan Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Our top choices for Sheboygan vacation rentals

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,015 reviews)
"Would definitely stay here again!"
United States
Donna
$125 nightly
The price is $142
Jan 14 - Jan 15
Total with taxes and fees
Grandstay Residential Suites Hotel - Sheboygan

Large Backyard, Walk to Hospital: Sheboygan Abode!

Large Backyard, Walk to Hospital: Sheboygan Abode!
3.0 star property
Sheboygan
$358 nightly
The price is $403
Jan 16 - Jan 17
Total with taxes and fees
Large Backyard, Walk to Hospital: Sheboygan Abode!

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.
$150 nightly
The price is $170
Jan 15 - Jan 16
Total with taxes and fees
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

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
9.8 out of 10, Exceptional, (9 reviews)
"The flat is gorgeous and in a fantastic location. "
United States
Sarah G.
$209 nightly
The price is $237
Jan 18 - Jan 19
Total with taxes and fees
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan
Sheboygan
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.
$271 nightly
The price is $308
Feb 1 - Feb 2
Total with taxes and fees
Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

Hot Tub, Fire Pit, Point Beach & Neshotah Beach

Hot Tub, Fire Pit, Point Beach & Neshotah Beach
2.0 star property
Two Rivers
$395 nightly
The price is $456
Jan 16 - Jan 17
Total with taxes and fees
Hot Tub, Fire Pit, Point Beach & Neshotah Beach

2nd floor loft near the lake!

2nd floor loft near the lake!
Manitowoc
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 14 - Jan 15
Total with taxes and fees
2nd floor loft near the lake!

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, (119 reviews)
"Rooms were clean, kitchen was adequate, laundry set up in one of the bedroom closets. Plenty of bedding and towels."
United States
Hallie R.
$140 nightly
The price is $148
Jan 14 - Jan 15
Total with taxes and fees
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Cabin on Lake 75 Acre Lake: Couples Get Away or Fun Family Vacation

Cabin on Lake 75 Acre Lake: Couples Get Away or Fun Family Vacation
2.0 star property
Fond du Lac
$735 nightly
The price is $775
Jan 14 - Jan 15
Total with taxes and fees
Cabin on Lake 75 Acre Lake: Couples Get Away or Fun Family Vacation

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, (24 reviews)
"Great place! Nice location and very comfortable. "
United States
Jana F.
$115 nightly
The price is $131
Jan 15 - Jan 16
Total with taxes and fees
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

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, (12 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.
$117 nightly
The price is $133
Jan 19 - Jan 20
Total with taxes and fees
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown

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.
2.0 star property
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.
$135 nightly
The price is $153
Jan 15 - Jan 16
Total with taxes and fees
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
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
Jan 14 - Jan 15
Total with taxes and fees
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

The Beach town bungalow

The Beach town bungalow
2.0 star property
Sheboygan
$198 nightly
The price is $201
Jan 14 - Jan 15
Total with taxes and fees
The Beach town bungalow

Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan

Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Sheboygan
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 14 - Jan 15
Total with taxes and fees
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan

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, (32 reviews)
"Adorable very clean cottage right on the river. Nice backyard with beautiful views and if you bring your furry friend, plenty of room for your doggie to roam and play out back. Close to beautiful Neshota Beach and lots of dining options. "
United States
Pamela S.
$188 nightly
The price is $213
Jan 15 - Jan 16
Total with taxes and fees
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

Luxury Suites #3

Luxury Suites #3
Brillion
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
$271 nightly
The price is $297
Jan 14 - Jan 15
Total with taxes and fees
Luxury Suites #3

Charming studio apartment - Perfect location for the outdoor explorer

Charming studio apartment - Perfect location for the outdoor explorer
Kewaskum
9.8 out of 10, Exceptional, (8 reviews)
"Perfect location friendly accommodating hosts!"
United States
steven s.
$290 nightly
The price is $305
Jan 14 - Jan 15
Total with taxes and fees
Charming studio apartment - Perfect location for the outdoor explorer

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Sheboygan
10.0 out of 10, Exceptional, (21 reviews)
"Wonderfully close to the lake. Sad there was no off street parking."
United States
Lucas T.
$316 nightly
The price is $359
Jan 14 - Jan 15
Total with taxes and fees
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater

Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater
4.0 star property
Fond du Lac
10.0 out of 10, Exceptional, (1 review)
"Our large family had a magical Christmas! Our beautifully decorated rented home had everything we needed . We were all very comfortable during the day and night time sleeping . We had private spaces and family get together areas ."
United States
Brenda J.
$2,866 nightly
The price is $3,253
Jan 19 - Jan 20
Total with taxes and fees
Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Sheboygan Hotel Reviews

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 $131 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.

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: Visitors give good reviews to this Sheboygan vacation home rental, which 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.

How many vacation rentals will I find in Sheboygan?

Choose from 97 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 Kohler Park Dunes State Natural Area, 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-Andrae State 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.