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Sheboygan Vacation Rentals

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Our top choices for Sheboygan vacation rentals

1. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,126 reviews)
"Quiet place near the lake."
United States
Vivian
The price is CA $168
CA $190 total
includes taxes & fees
Nov 8 - Nov 9
Grandstay Residential Suites Hotel - Sheboygan

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

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Ellis Historical District
9.4 out of 10, Exceptional, (40 reviews)
"Very quiet, and only two blocks from Lake Michigan"
United States
Terri
The price is CA $91
CA $108 total
includes taxes & fees
Nov 8 - Nov 9
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

3. 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, (33 reviews)
"The location was perfect to experience the Art Fair, downtown, and the area overall!Clean & comfortable - would return!"
United States
Andrea L.
The price is CA $288
CA $528 total
includes taxes & fees
Nov 8 - Nov 9
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

4. 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
9.8 out of 10, Exceptional, (12 reviews)
"Close to everything we were looking to do while visiting the area. Great communication and hospitality from host, would stay again!!"
United States
Heidi
The price is CA $119
CA $231 total
includes taxes & fees
Nov 8 - Nov 9
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan

5. Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (32 reviews)
"It suited our needs. Interior lighting was a bit harsh"
United States
James
The price is CA $158
CA $502 total
includes taxes & fees
Nov 9 - Nov 10
Sleeps 8 & Spacious!

6. 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, (151 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is CA $176
CA $203 total
includes taxes & fees
Nov 9 - Nov 10
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

7. 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
9.8 out of 10, Exceptional, (43 reviews)
"Great place close to everything we needed. Walking distance to the coffee shop, beach, bar, and pizza place. Not much more you really need."
United States
Gregory D.
The price is CA $440
CA $801 total
includes taxes & fees
Nov 6 - Nov 7
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

8. Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.4 out of 10, Exceptional, (9 reviews)
"We had a great time up there and the host was excellent and the property was fantastic"
United States
Alex N.
The price is CA $131
CA $403 total
includes taxes & fees
Nov 8 - Nov 9
Logan Ave Holiday House - Upper

9. 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
9.8 out of 10, Exceptional, (8 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 CA $133
CA $259 total
includes taxes & fees
Nov 10 - Nov 11
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

10. Beautiful & Convenient!

Beautiful & Convenient!
Sheboygan
9.8 out of 10, Exceptional, (23 reviews)
"Wonderful property! Communication was wonderful and so very helpful at all times. Not far from the marina, where we spent a lot of our time. "
United States
Susan G.
The price is CA $170
CA $468 total
includes taxes & fees
Nov 9 - Nov 10
Beautiful & Convenient!

11. 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 CA $93
CA $799 total
includes taxes & fees
Nov 9 - Nov 10
Victorian Inn Elkhart Lake Wisconsin

12. 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, (15 reviews)
"We enjoyed our stay! The property was clean, "
United States
Benjamin B.
The price is CA $119
CA $242 total
includes taxes & fees
Nov 8 - Nov 9
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

13. Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan

Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
Sheboygan
10.0 out of 10, Exceptional, (1 review)
"Great location, centrally located, clean and well-furnished. Ginger was a great host, very accommodating."
United States
Tonja K.
The price is CA $133
CA $266 total
includes taxes & fees
Nov 9 - Nov 10
Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan

14. 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, (43 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 CA $163
CA $512 total
includes taxes & fees
Nov 9 - Nov 10
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

15. Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair

Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
Sheboygan
10.0 out of 10, Exceptional, (2 reviews)
"Very nice place. The owners were very helpful during our stay with recommendations on things to do as our fishing trip was cancelled!"
United States
Nicole B.
The price is CA $369
CA $455 total
includes taxes & fees
Nov 8 - Nov 9
Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair

16. Just Beachy: 4 Bedroom, Sleeps 12!

Just Beachy: 4 Bedroom, Sleeps 12!
Sheboygan
8.6 out of 10, Excellent, (8 reviews)
"The condo was very clean and comfortable. It was just steps from the lake. It's a great place to stay!"
United States
Erika M.
The price is CA $622
CA $1,099 total
includes taxes & fees
Nov 6 - Nov 7
Just Beachy: 4 Bedroom, Sleeps 12!

17. Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Sheboygan
10.0 out of 10, Exceptional, (9 reviews)
"We stayed a very short time due to many wedding details and festivities and the stay was just what we needed. Convenient to wedding location, very clean, comfy beds, friendly and reliable host! Would highly recommend!"
United States
Stephanie M.
The price is CA $161
CA $298 total
includes taxes & fees
Nov 30 - Dec 1
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

18. The Links! - Luxury Golf Retreat with Golf Simulator

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (16 reviews)
"Perfect trip and great location"
United States
Kristian N.
The price is CA $329
CA $836 total
includes taxes & fees
Nov 8 - Nov 9
The Links! - Luxury Golf Retreat with Golf Simulator

19. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (73 reviews)
"Absolutely Beautiful. Great, quiet location...clean and well kept. Recommend buying some of their amazing home made maple syrup!!"
United States
Barbara
The price is CA $278
CA $366 total
includes taxes & fees
Nov 10 - Nov 11
The Esker Ridge Chalet, Pristine Elkhart Solitude

20. Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.

Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.
Sheboygan
10.0 out of 10, Exceptional, (17 reviews)
"Everything was clean and spacious. Had a great time and would definitely stay again! "
United States
Brad T.
The price is CA $801
CA $1,351 total
includes taxes & fees
Nov 8 - Nov 9
Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.
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

Find out more about Sheboygan

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Sheboygan. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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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 scenic lakeside 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 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 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.