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Sheboygan Vacation Rentals

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Vacation Rentals in Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
Lobby
Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
8.6 out of 10, Excellent, (807)
"The rooms are spacious and clean. It’s close to restaurants. "
The price is CA $203
CA $230 total
includes taxes & fees
May 30 - May 31
Grandstay Residential Suites Hotel - Sheboygan
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Property grounds
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
9.8 out of 10, Exceptional, (215)
"What a relaxing getaway for us who are busy raising three kids- 21,17 and 14. It’s been well over a decade since we did anything as husband and wife, without the kids. We grew up in Port Washington and savored being on Lake Michigan on two beautiful Spring Days. We took lots of walks and ate take out on the patio. With such views who needs a restaurant?? A total gem of a place, we will be back again. Thank you Mark!!"
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
REMODELED HOME ON LAKE MICHIGAN
REMODELED HOME ON LAKE MICHIGAN
10.0 out of 10, Exceptional, (142)
"Great location and view of the lake. The kitchen is one of the best stocked I have seen in a while. Good layout for hanging out. Communication was easy."
REMODELED HOME ON LAKE MICHIGAN
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*NEW* Sleeps 8 & Spacious!
TV
*NEW* Sleeps 8 & Spacious!
10.0 out of 10, Exceptional, (12)
"Would highly recommend! It was very clean and newly remodeled. Had everything we needed and we felt right at home!"
The price is CA $146
CA $532 total
includes taxes & fees
Jun 2 - Jun 3
*NEW* Sleeps 8 & Spacious!
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Private kitchen
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
10.0 out of 10, Exceptional, (2)
"Clean, well-organized, plenty of seating, pool table, darts and arcade games. Fourth bedroom is only accessible through bathroom or another bedroom."
The price is CA $239
CA $576 total
includes taxes & fees
Jun 11 - Jun 12
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
3 Bedroom Beach House
Golf
3 Bedroom Beach House
10.0 out of 10, Exceptional, (6)
"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
Perfect Paradise : Luxury Beachfront Condo!
On the beach, sun loungers, beach towels
Perfect Paradise : Luxury Beachfront Condo!
10.0 out of 10, Exceptional, (2)
"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!
Edgewater Escapes - 4 bed condo steps to the lake
Beach
Edgewater Escapes - 4 bed condo steps to the lake
9.2 out of 10, Wonderful, (9)
"Place was great! Awesome location and lots of room."
The price is CA $819
CA $1,372 total
includes taxes & fees
Jun 3 - Jun 4
Edgewater Escapes - 4 bed condo steps to the lake
Family-Friendly House: Walk to Lake Michigan!
Fridge, microwave, stovetop, dishwasher
Family-Friendly House: Walk to Lake Michigan!
10.0 out of 10, Exceptional, (2)
"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!
Beach front luxury spacious villa !
Interior
Beach front luxury spacious villa !
10.0 out of 10, Exceptional, (30)
"Great experience, would definitely recommend to anyone. Quality in every finish of the place. Will definitely make this our main home away from home when going on golf trips."
Beach front luxury spacious villa !
Walk to beach, restaurants, shops! Historic charm with updated amenities
Sun loungers, beach towels
Walk to beach, restaurants, shops! Historic charm with updated amenities
10.0 out of 10, Exceptional, (44)
"Carefully renovated home with charm and amenities for a lovely stay. Great location in quiet residental neighborhood close to the Lake and all that Sheboygan has to offer."
Walk to beach, restaurants, shops! Historic charm with updated amenities
Cozy 2 bd home, minutes from lake Michigan
Living area
Cozy 2 bd home, minutes from lake Michigan
7.4 out of 10, Good, (11)
"Cute place, very clean. Communication has been great, everything from check in through the stay has been easy and smooth!"
The price is CA $205
CA $381 total
includes taxes & fees
Jun 3 - Jun 4
Cozy 2 bd home, minutes from lake Michigan
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub
Property grounds
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub
10.0 out of 10, Exceptional, (157)
"The property is clean, nice, and very welcoming. We enjoyed our stay from the moment we got on property. Highly recommend this property as we will be staying here next time in town!"
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
Lake
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
9.8 out of 10, Exceptional, (67)
"Very nice condo.. spacious, clean and well-stocked. Loved being on the water and the decks to sit outside. We would definitely stay here again!"
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
Updated Sheboygan Home w/ Porch < 1 Mi to Beach
TV, fireplace
Updated Sheboygan Home w/ Porch < 1 Mi to Beach
9.8 out of 10, Exceptional, (36)
"pros Perfect location, a cute neighborhood. house had everything you could want to make your stay perfect. Clean, nice bathrooms, heater in LR worked really well. Beautiful furnishings and, nice "local book" , although we would've liked to have more info on the history of the property. comfy beds we were able to checkout late since no one was staying after us and they approved us to stay later. That was awesome since we arrived really late. due to it being winter, didnt get a chance to enjoy the...
Updated Sheboygan Home w/ Porch < 1 Mi to Beach
Fairway Getaway-by Whistling Straits, Golf sim/Theater Room, ZenDen &Poker Room!
Smart TV, video games
Fairway Getaway-by Whistling Straits, Golf sim/Theater Room, ZenDen &Poker Room!
10.0 out of 10, Exceptional, (1)
"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...
Fairway Getaway-by Whistling Straits, Golf sim/Theater Room, ZenDen &Poker Room!
Sheboygan Getaway w/ Deck + On-Site Lake Access!
Fridge, microwave, stovetop, dishwasher
Sheboygan Getaway w/ Deck + On-Site Lake Access!
10.0 out of 10, Exceptional, (1)
"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!
Property grounds
Shoreline Sanctuary - a Lakefront Retreat!
Shoreline Sanctuary - a Lakefront Retreat!
BEACHSIDE GETAWAY IN SHEBOYAN
Fridge, microwave, oven, stovetop
BEACHSIDE GETAWAY IN SHEBOYAN
10.0 out of 10, Exceptional, (10)
"Well equipped and comfortable for a full week’s stay. Loved access to the beach for sunrise walks."
BEACHSIDE GETAWAY IN SHEBOYAN
4 Bedroom Beachfront Condo
Property grounds
4 Bedroom Beachfront Condo
10.0 out of 10, Exceptional, (46)
"The property and location were awesome. We were close to everything. The house was stocked better than any place we’ve stayed. The view was beautiful, day and night. We were blessed with a full moon which just topped it off. The trees were in full bloom which almost made up for the weather being a little chilly and rainy."
4 Bedroom Beachfront Condo
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
Exterior
La Quinta Inn by Wyndham Sheboygan
2.5 star property
8.0 out of 10, Very good, (1000)
"Always our go to place to stay when in Sheboygan."
The price is CA $118
CA $133 total
includes taxes & fees
Jun 24 - Jun 25
La Quinta Inn by Wyndham Sheboygan
Grandstay Residential Suites Hotel - Sheboygan
Lobby
Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
8.6 out of 10, Excellent, (807)
"The rooms are spacious and clean. It’s close to restaurants. "
The price is CA $203
CA $230 total
includes taxes & fees
May 30 - May 31
Grandstay Residential Suites Hotel - Sheboygan
Blue Harbor Resort and Conference Center
Breakfast, dinner, brunch served; Regional cuisine, beach views
Blue Harbor Resort and Conference Center
3.0 star property
8.4 out of 10, Very good, (413)
"Nice property in a beautiful location. Nice amenities. "
The price is CA $292
CA $366 total
includes taxes & fees
May 30 - May 31
Blue Harbor Resort and Conference Center
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
Expedia verified reviews

La Quinta Inn by Wyndham Sheboygan

La Quinta Inn by Wyndham Sheboygan

5/5 Excellent
"Always our go to place to stay when in Sheboygan."
A verified traveller stayed at La Quinta Inn by Wyndham Sheboygan
Posted 7 days ago
La Quinta Inn by Wyndham Sheboygan