Photo by ed lee schneider

Sheboygan Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Find properties with these dates

Tonight
May 1 - May 2
Tomorrow
May 2 - May 3
This weekend
May 3 - May 5
Next weekend
May 10 - May 12

Holiday Rentals in Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
Lobby
Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
8.6 out of 10, Excellent, (795)
"Great space very upgraded for that price! Roomy and comfortable suites!! "
The price is HK$1,047
HK$1,189 total
includes taxes & fees
15 May - 16 May
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, (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!
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
*NEW* Sleeps 8 & Spacious!
TV
*NEW* Sleeps 8 & Spacious!
10.0 out of 10, Exceptional, (10)
"My friends and I rented this property as a short vacation. We began working on a cookbook and had a great time. The property was very clean and well maintained. It was more than we imagined. We will consider going back to rent again."
The price is HK$647
HK$2,799 total
includes taxes & fees
7 May - 8 May
*NEW* Sleeps 8 & Spacious!
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
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 HK$1,174
HK$3,046 total
includes taxes & fees
7 May - 8 May
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
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!
Downtown waterfront condo. Full hook-up boat slip! Close to beach! Private deck!
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!
Beach front luxury spacious villa !
Interior
Beach front luxury spacious villa !
10.0 out of 10, Exceptional, (30)
"I recently stayed at the lake house for a bachelorette party, and it was an absolute dream! The house was impeccably clean, creating a cozy and inviting atmosphere that was perfect for our celebration. The views of the lake were breathtaking, offering a serene backdrop for our weekend getaway. The host was incredibly communicative, making sure that all our needs were met and providing helpful tips for exploring the area. Overall, it was an unforgettable experience, and I highly recommend this...
Beach front luxury spacious villa !
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, (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
Cozy 2 bd home, minutes from lake Michigan
Living area
Cozy 2 bd home, minutes from lake Michigan
7.0 out of 10, Good, (10)
"The property was nice. Clean except for floors. Beds were comfortable. TV was a bit tuff to navigate. Back yard needs cleaned a bit. We had our dog and it was nice the yard was fenced."
The price is HK$1,174
HK$2,185 total
includes taxes & fees
2 May - 3 May
Cozy 2 bd home, minutes from lake Michigan
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
Lake
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
9.8 out of 10, Exceptional, (64)
"We were in Sheboygan for a wedding at Blue Harbor-the condo was perfect for our group! Clean, comfy beds, lots of towels and we felt at home. Walking distance to many good restaurants-loved Harry's Prohibition and Driftwood! Nice views of the river from the 2 balcony's, stocked kitchen and easy check in and out. Thanks for the use of the condo-hope to return on our next Sheboygan trip!"
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
BEACHSIDE GETAWAY IN SHEBOYAN
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
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!
5 Bedroom Modern House
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
Shoreline Sanctuary - a Lakefront Retreat!
Property grounds
Shoreline Sanctuary - a Lakefront Retreat!
Shoreline Sanctuary - a Lakefront Retreat!
4 Bedroom Beachfront Condo
Property grounds
4 Bedroom Beachfront Condo
10.0 out of 10, Exceptional, (44)
"This was our second stay at this condo and we absolutely loved it again! The view is so beautiful and the property is very well kept!"
4 Bedroom Beachfront Condo
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Aerial view
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!
The Suncatcher- Pet Friendly, 1 block to lake
Fridge, microwave, oven, stovetop
The Suncatcher- Pet Friendly, 1 block to lake
10.0 out of 10, Exceptional, (4)
"If I could give 6 stars, I would. This place is truly a gem in a wonderful town. Suncatcher is the perfect name, as there are so many accents of sunshine throughout. The amenities are out of this world! Fully stocked kitchen, two showers with everything you need, games, comfy sitting areas,( that couch is 100!), a fireplace(!!), and the perfect amount of space for three women who need to get away from it all! (Also…there is a cheese themed bedroom that I didn’t know I needed in my life.) So...
The price is HK$1,174
HK$2,939 total
includes taxes & fees
7 May - 8 May
The Suncatcher- Pet Friendly, 1 block to lake
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...
The price is HK$19,559
HK$28,602 total
includes taxes & fees
15 May - 16 May
Fairway Getaway-by Whistling Straits, Golf sim/Theater Room, ZenDen &Poker Room!
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

AmericInn by Wyndham Sheboygan
Lobby
AmericInn by Wyndham Sheboygan
2.0 star property
8.6 out of 10, Excellent, (924)
"Beds were a bit hard for our taste. The pillows were ok. The drain stopper in bathroom sink came off. MLB channel was listed but not available"
The price is HK$632
HK$717 total
includes taxes & fees
5 May - 6 May
AmericInn by Wyndham Sheboygan
La Quinta Inn by Wyndham Sheboygan
Exterior
La Quinta Inn by Wyndham Sheboygan
2.5 star property
8.0 out of 10, Very good, (1001)
"Very nice!"
The price is HK$632
HK$717 total
includes taxes & fees
7 May - 8 May
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, (795)
"Great space very upgraded for that price! Roomy and comfortable suites!! "
The price is HK$1,047
HK$1,189 total
includes taxes & fees
15 May - 16 May
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.

Search for holiday rentals in Sheboygan on Expedia! You can easily find your home rentals, villas, holiday apartments in Sheboygan using one of the methods below:

  • View our selection of featured holiday rentals in Sheboygan
  • Use the map to find apartments and other holiday homes in the Sheboygan neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sheboygan while they last

Look no further and take a look at our great range of rental properties in Sheboygan!

Frequently asked questions

Can I find a holiday rental in Sheboygan?

Yes, there are holiday rentals in Sheboygan close to Blue Harbor Resort & Conference Center Water Park, or you can select a more secluded option if you're looking for 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 holiday rentals that Sheboygan has to offer?

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!: This highly rated holiday home rental in Sheboygan is located on a lake, and has a fireplace, a balcony and a BBQ 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 holiday with amenities such as a selection of games. Our travellers also rate REMODELED HOME ON LAKE MICHIGAN as a favourite home for rent in Sheboygan.

How many holiday rentals will I find in Sheboygan?

Choose from 90 Expedia holiday rentals in Sheboygan for a memorable holiday.

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 holiday rental in Sheboygan like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sheboygan. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a family trip.

Recent reviews of Sheboygan properties
Expedia verified reviews

Inn of Sheboygan

Inn of Sheboygan

5/5 Excellent
"This is a renovated motel that is clean & in a great location — within walking distance of downtown shopping & dining. Our room with a king bed was clean & updated, but it was compact. The bathroom was definitely small — not a lot of room for toiletries & the toilet was super close to the door & at an awkward angle. Other than that this is a great place to stay if you want convenient downtown access, somewhere safe, & a super clean environment."
A verified traveller from Onalaska stayed at Inn of Sheboygan
Posted 2 days ago
Inn of Sheboygan