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Sheboygan Vacation Rentals

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Vacation Rentals in Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
8.6 out of 10, Excellent, 814 reviews
"Nothing unique, clean, good wi-fi."
The price is CA $232
CA $263 total
includes taxes & fees
Jun 16 - Jun 17
Grandstay Residential Suites Hotel - Sheboygan
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
9.8 out of 10, Exceptional, 217 reviews
"Very nice kitchen and living room. Small TV. Both bedrooms are on second floor with bath/shower on main living area. Lots of stairs, so if you have bad knees this place isn't for you. But the sunrises were amazing and it was quiet and so pleasant to sit out on the back deck on a cliff over looking Lake Michigan. Great location in Sheboygan."
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
REMODELED HOME ON LAKE MICHIGAN
10.0 out of 10, Exceptional, 143 reviews
"Easy check in, very clean."
REMODELED HOME ON LAKE MICHIGAN
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
10.0 out of 10, Exceptional, 3 reviews
"Very clean property, comfortable beds, and plenty to do for kids and adults alike."
The price is CA $240
CA $579 total
includes taxes & fees
Jun 17 - Jun 18
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
*NEW* Sleeps 8 & Spacious!
10.0 out of 10, Exceptional, 12 reviews
"Would highly recommend! It was very clean and newly remodeled. Had everything we needed and we felt right at home!"
The price is CA $147
CA $535 total
includes taxes & fees
Jun 17 - Jun 18
*NEW* Sleeps 8 & Spacious!
Family-Friendly House: Walk to Lake Michigan!
9.4 out of 10, Exceptional, 3 reviews
"My family and I were in town for Christmas, and the house served as a great spot of us to hang our hats. Mike was a tremendous host who was very quick to respond to any questions. He even ensured that the house was pleasantly decorated for the season. The house is conveniently situated between town (~3 blocks) and the lake Michigan beaches (~2 blocks). We found the kitchen to be fully equipped and included a selection of K-cups for us to enjoy each morning. Most importantly, the house was clean...
Family-Friendly House: Walk to Lake Michigan!
3 Bedroom Beach House
10.0 out of 10, Exceptional, 6 reviews
"The owner was super amazing helping us reschedule our trip. The house was clean and the beds and pillows were very comfortable. I looked up what they were to order them :) Lots of food and bars close enough to walk to. Very close to the lake too."
3 Bedroom Beach House
Edgewater Escapes - 4 bed condo steps to the lake
9.2 out of 10, Wonderful, 9 reviews
"Place was great! Awesome location and lots of room."
The price is CA $823
CA $1,380 total
includes taxes & fees
Jun 18 - Jun 19
Edgewater Escapes - 4 bed condo steps to the lake
Perfect Paradise : Luxury Beachfront Condo!
10.0 out of 10, Exceptional, 2 reviews
"The property was excellent. Clean and comfortable. Great location with close proximity to Blackwolf Run and Whistling Straits. Enjoyed our time at the property. Will rent again next year."
Perfect Paradise : Luxury Beachfront Condo!
Beach front luxury spacious villa !
10.0 out of 10, Exceptional, 32 reviews
"Very nice place. Much appreciated."
Beach front luxury spacious villa !
Cozy 2 bd home, minutes from lake Michigan
7.4 out of 10, Good, 11 reviews
"Cute place, very clean. Communication has been great, everything from check in through the stay has been easy and smooth!"
The price is CA $206
CA $382 total
includes taxes & fees
Jun 18 - Jun 19
Cozy 2 bd home, minutes from lake Michigan
Walk to beach, restaurants, shops! Historic charm with updated amenities
10.0 out of 10, Exceptional, 46 reviews
"We really enjoyed our stay in this well-appointed, cozy house. Downtown and the beach were both walkable from the house, which made it easy to get around. Our hosts provided good info about local places to eat and visit and were very responsive. Overall, just an excellent, welcoming place!"
Walk to beach, restaurants, shops! Historic charm with updated amenities
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub
10.0 out of 10, Exceptional, 158 reviews
"Quiet neighborhood, clean accomodations."
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
9.8 out of 10, Exceptional, 68 reviews
"Beautiful, comfortable, well stocked condo (towels, paper products, etc.). Exceptionally clean. Enjoyed our stay."
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
Fairway Getaway-by Whistling Straits, Golf sim/Theater Room, ZenDen &Poker Room!
10.0 out of 10, Exceptional, 1 review
"Shawn has created an ideal getaway and we all highly recommend staying here. Everything was brand new and very clean. We had so much fun staying here for our friend's 40th birthday. There were 10 adults and we all had a comfortable place to sleep. The space is perfect for large groups and you could throw an amazing party. I would love to return in warmer weather and enjoy more time on the deck and front patio. There are spacious gathering areas and small quiet areas for when you need a little...
The price is CA $1,852
CA $3,025 total
includes taxes & fees
Jun 16 - Jun 17
Fairway Getaway-by Whistling Straits, Golf sim/Theater Room, ZenDen &Poker Room!
Sheboygan Getaway w/ Deck + On-Site Lake Access!
10.0 out of 10, Exceptional, 1 review
"I felt is was exactly what i expected as per viewing pictures and description. Deck was an extra fun thing to be able to see Lake Michigan and watch the sunrise, we will be back !"
Sheboygan Getaway w/ Deck + On-Site Lake Access!
Shoreline Sanctuary - a Lakefront Retreat!
Shoreline Sanctuary - a Lakefront Retreat!
BEACHSIDE GETAWAY IN SHEBOYAN
10.0 out of 10, Exceptional, 10 reviews
"We had a great stay at the property!"
BEACHSIDE GETAWAY IN SHEBOYAN
4 Bedroom Beachfront Condo
10.0 out of 10, Exceptional, 48 reviews
"Property extremely well appointed with ample sleeping arrangements for up to 10. Easy check in/check out with clear instructions. Would book again in future"
4 Bedroom Beachfront Condo
Lovely Lake Lookout - Beachfront Condo mins to Lake Michigan!
9.6 out of 10, Exceptional, 4 reviews
"The home was clean and has plenty of room to sleep a lot of people. It is only about 2 blocks from the beach and some shops. They thought of everything including floss and a makeup remover in each bathroom. The kitchen is well stocked with all that we needed."
Lovely Lake Lookout - Beachfront Condo mins to Lake Michigan!
Don't see what you're looking for?
See all available properties in Sheboygan
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.

Other types of properties in Sheboygan you may be interested in

La Quinta Inn by Wyndham Sheboygan
2.5 star property
8.0 out of 10, Very good, 1,001 reviews
"I was in town for the Golf Tournament and stayed an extra day. The area is beautiful and my stay was nice and quiet."
The price is CA $118
CA $134 total
includes taxes & fees
Jul 1 - Jul 2
La Quinta Inn by Wyndham Sheboygan
Blue Harbor Resort and Conference Center
3.0 star property
8.4 out of 10, Very good, 416 reviews
"Room was super clean, beds were comfortable, check-in was easy!"
Blue Harbor Resort and Conference Center
Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
8.6 out of 10, Excellent, 814 reviews
"Nothing unique, clean, good wi-fi."
The price is CA $232
CA $263 total
includes taxes & fees
Jun 16 - Jun 17
Grandstay Residential Suites Hotel - Sheboygan
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.

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.

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?

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 a barbecue grill 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 90 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-Andrae State Park, 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 Whistling Straits Golf Course 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.

Recent reviews of Sheboygan properties
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