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Sheboygan Vacation Rentals

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Vacation Rentals in Sheboygan

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
TV
*NEW* Sleeps 8 & Spacious!
10.0 out of 10, Exceptional, (11)
"The property was perfect for our needs (space & rooms & beds). The house was clean and communication was excellent. Check-in & check-out were easy. We would definitely consider staying again. The only surprise was that this was an apartment building and this space was on the second floor."
The price is CA $127
CA $506 total
includes taxes & fees
May 22 - May 23
*NEW* Sleeps 8 & Spacious!
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 $184
CA $503 total
includes taxes & fees
May 20 - May 21
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
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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
On the beach, sun loungers, beach towels
Perfect Paradise : Monthly Stays Welcome!
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 : Monthly Stays Welcome!
Property grounds
Downtown waterfront condo. Full hook-up boat slip! Close to beach! Private deck!
10.0 out of 10, Exceptional, (60)
"We enjoyed a relaxing weekend here and appreciated the location as well as the peaceful atmosphere and view of the water."
Downtown waterfront condo. Full hook-up boat slip! Close to beach! Private deck!
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 !
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!
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
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, (156)
"Everything went well with our stay. Thank you."
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub
Highchair
3 blocks from Lake Spacious Entire Place 1 BDRM full bath 5 min to downtown
10.0 out of 10, Exceptional, (1)
"From the begining of the reservation we had great communication with the host. They gave us ideas of places to visit after asking a few questions. They sent check in messages to see if we needed anything or were doing ok. The location was well stocked in the kitchen and bathroom, they even had things if we forgot anything. Nice and bright space. Good neighborhood and nice porch to sit on. The location was close to everything we hoped to get to: state park, downtown, beach, walking trails. It...
The price is CA $135
CA $315 total
includes taxes & fees
May 23 - May 24
3 blocks from Lake Spacious Entire Place 1 BDRM full bath 5 min to downtown
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!
Fridge, microwave, oven, stovetop
BEACHSIDE GETAWAY IN SHEBOYAN
10.0 out of 10, Exceptional, (9)
"Fantastic friends' getaway; with beautiful views of the lake from the front and back patio doors and decks. Walk right out and you're within steps of the beach and a close walk to South Pier. Will stay here again."
BEACHSIDE GETAWAY IN SHEBOYAN
Property grounds
4 Bedroom Beachfront Condo
10.0 out of 10, Exceptional, (45)
"Great view, super clean. This host clearly put a lot of effort into making sure we had a nice stay."
4 Bedroom Beachfront Condo
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!
Golf
5 Bedroom Modern House
10.0 out of 10, Exceptional, (4)
"Home was perfect for our weekend in Sheboygan. Great location and very clean. We left an expensive electric toothbrush behind and the owner was kind enough to ship it to us! We'll be back!"
5 Bedroom Modern House
Fridge, microwave, stovetop, dishwasher
Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan
10.0 out of 10, Exceptional, (12)
"Liked it can meet our needs very well ."
Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan
Dining
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
10.0 out of 10, Exceptional, (5)
"Place was off the charts. Great! Host was responsive. Property was spotless perfect place to spend time with friends and family if I can give more than five stars I would."
The price is CA $204
CA $513 total
includes taxes & fees
May 21 - May 22
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Fridge, microwave, stovetop, dishwasher
Downtown Sheboygan Apartment w/ Private Deck!
10.0 out of 10, Exceptional, (2)
"Fantastic location in downtown Sheboygan, host was easy to contact and answered all questions."
Downtown Sheboygan Apartment w/ Private Deck!
Property grounds
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
9.8 out of 10, Exceptional, (214)
"100% recommend staying here! The views were incredible! The photos in the listing don’t do it justice! Being able to watch the sunrise and see the full moon over the lake from the balcony was stunning! The large windows and slider doors allow you to view the lake when you’re cooking and eating as well! We also brought our dogs which is something that usually makes it difficult to travel! But they were welcomed and had a blast being with us! Dog gates and sheets to cover the couch were provided...
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
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

Exterior
Watershed Hotel
3.0 star property
9.8 out of 10, Exceptional, (213)
"The hotel facilities are beautiful, modern and very clean. We had a room facing the river on the first floor, the view was incredible! However, if you are looking for a quiet place, you can hear other guest walking around on the second floor, opening and closing doors, and chatting as if they were in the same room with you! Other than that staff was nice and friendly and continental breakfast was good. "
The price is CA $252
CA $286 total
includes taxes & fees
May 17 - May 18
Watershed Hotel
Lobby
Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
8.6 out of 10, Excellent, (797)
"Great space very upgraded for that price! Roomy and comfortable suites!! "
The price is CA $202
CA $230 total
includes taxes & fees
May 19 - May 20
Grandstay Residential Suites Hotel - Sheboygan
Lobby
AmericInn by Wyndham Sheboygan
2.0 star property
8.6 out of 10, Excellent, (929)
"Check in was easy and friendly. The room was clean, the tv and WiFi worked fine. We only spent one night and didn’t use the pool or do any sightseeing in the area. The pillows on the bed were small and hard. We did manage to sleep but were woken up at 6:30 am by beeping from a vehicle at the company next door. This hotel is right next to the freeway in an industrial area, so they have limited control over what the neighbors are doing, but it was very unpleasant. We had not planned to get...
The price is CA $138
CA $156 total
includes taxes & fees
Jun 9 - Jun 10
AmericInn by Wyndham 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.

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sheboygan vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sheboygan vacation rentals we have selected for you start as low as CA $127 per night. Entering your travel dates in the search wizard 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?

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

Harbor Winds Hotel

Harbor Winds Hotel

5/5 Excellent
"Great stay! "
A verified traveller stayed at Harbor Winds Hotel
Posted 2 days ago
Harbor Winds Hotel