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Sheboygan Holiday Rentals

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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Sheboygan holiday rentals

Lobby
Grandstay Residential Suites Hotel - Sheboygan

Aparthotel in Downtown Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
8.6 out of 10, Excellent, (1015)
"Would definitely stay here again!"
United States
Donna
The price is HK$972
HK$1,103 total
includes taxes & fees
4 Jan - 5 Jan
Grandstay Residential Suites Hotel - Sheboygan
Fridge, microwave, oven, stovetop
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler

Holiday Home in Kiel

Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
2.0 star property
10.0 out of 10, Exceptional, (3)
"Wonderful place! "
United States
Colleen & Mark G.
The price is HK$2,802
HK$4,746 total
includes taxes & fees
12 Jan - 13 Jan
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
Property grounds
tranquil cabin on 5 private acres w/ hot tub and sauna

Cabin in Cascade

tranquil cabin on 5 private acres w/ hot tub and sauna
10.0 out of 10, Exceptional, (11)
"This was a lovely property and truly a place to relax and recharge. We enjoyed our stay! "
United States
Kelly D.
The price is HK$2,226
HK$2,685 total
includes taxes & fees
11 Jan - 12 Jan
tranquil cabin on 5 private acres w/ hot tub and sauna
Interior
Large Backyard, Walk to Hospital: Sheboygan Abode!

Cottage in Sheboygan

Large Backyard, Walk to Hospital: Sheboygan Abode!
3.0 star property
The price is HK$1,144
HK$3,134 total
includes taxes & fees
3 Jan - 4 Jan
Large Backyard, Walk to Hospital: Sheboygan Abode!
Dining
Beautiful private home hidden in the woods. Can sleep 11 guests

Holiday Home in Plymouth

Beautiful private home hidden in the woods. Can sleep 11 guests
10.0 out of 10, Exceptional, (14)
"Very clean and private property! "
United States
sherine m.
The price is HK$6,226
HK$7,505 total
includes taxes & fees
10 Jan - 11 Jan
Beautiful private home hidden in the woods. Can sleep 11 guests
Property grounds
Waterfront Condo, Private Beach, Outdoor/Indoor Pools, & Walkable to Downtown

Condo in Elkhart Lake

Waterfront Condo, Private Beach, Outdoor/Indoor Pools, & Walkable to Downtown
10.0 out of 10, Exceptional, (8)
"Definitely recommend this unit and owner. "
United States
Patty M.
The price is HK$1,891
HK$3,923 total
includes taxes & fees
3 Jan - 4 Jan
Waterfront Condo, Private Beach, Outdoor/Indoor Pools, & Walkable to Downtown
Exterior
Cabin on Lake 75 Acre Lake: Couples Get Away or Fun Family Vacation

Cabin in Fond du Lac

Cabin on Lake 75 Acre Lake: Couples Get Away or Fun Family Vacation
2.0 star property
The price is HK$1,245
HK$5,986 total
includes taxes & fees
15 Jan - 16 Jan
Cabin on Lake 75 Acre Lake: Couples Get Away or Fun Family Vacation
Property grounds
NEW Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!

Condo in Sheboygan

NEW Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!
2.0 star property
10.0 out of 10, Exceptional, (7)
The price is HK$1,518
HK$2,563 total
includes taxes & fees
31 Jan - 1 Feb
NEW Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!
Exterior detail
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

Holiday Home in New Holstein

Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
10.0 out of 10, Exceptional, (173)
"Great place would go back"
United States
William
The price is HK$1,576
HK$2,607 total
includes taxes & fees
8 Jan - 9 Jan
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
Private kitchen
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.

Holiday Home in Ellis Historical District

Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
2.0 star property
9.6 out of 10, Exceptional, (12)
"A warm and cozy place to stay. Beautifully decorated and friendly hosts. Would stay again anytime we’re in Sheboygan."
United States
Rebecca S.
The price is HK$895
HK$1,193 total
includes taxes & fees
19 Jan - 20 Jan
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
Property grounds
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

Holiday Home in Reedsville

Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
9.8 out of 10, Exceptional, (32)
"Great place for family to stay for wedding of grandson. "
United States
Dawn C.
The price is HK$2,335
HK$3,687 total
includes taxes & fees
4 Jan - 5 Jan
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Microwave, oven, stovetop, dishwasher
3 Min to Road America, outdoor deck, grill, & fire table

Holiday Home in Plymouth

3 Min to Road America, outdoor deck, grill, & fire table
10.0 out of 10, Exceptional, (1)
"This place was perfect for our group. We were karting at Road America, and location was a little over a mile from the gate. Newly renovated and very nice. Hosts did lots of little things to add value to our stay. Plenty to do nearby. Kids loved the basement and yard, adults hung out on patio. Would definitely stay here again. "
United States
Matt W.
The price is HK$2,724
HK$6,052 total
includes taxes & fees
20 Jan - 21 Jan
3 Min to Road America, outdoor deck, grill, & fire table
Fridge, microwave, oven, stovetop
5 min from Road America. Great yard and plenty of parking

Holiday Home in Elkhart Lake

5 min from Road America. Great yard and plenty of parking
10.0 out of 10, Exceptional, (2)
" We enjoyed our stay very much. The house is lovely, spacious, and clean. The property is quite big and provides an excellent space to walk or room for younger children to play. Several family members enjoyed a walk about after our drive on Saturday. The house was perfect for our group, and the living room was our gathering place for Saturday evening as well as Sunday morning. We cooked our evening meal and our morning breakfast in the kitchen. The only minor issue was that our group had 9...
United States
Paul & Jacqleene M.
The price is HK$6,421
HK$9,615 total
includes taxes & fees
1 Feb - 2 Feb
5 min from Road America. Great yard and plenty of parking
Fridge, microwave, oven, stovetop
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

Apartment in Ellis Historical District

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
9.8 out of 10, Exceptional, (24)
"Great place! Nice location and very comfortable. "
United States
Jana F.
The price is HK$739
HK$1,016 total
includes taxes & fees
4 Jan - 5 Jan
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Exterior
Charming studio apartment - Perfect location for the outdoor explorer

Apartment in Kewaskum

Charming studio apartment - Perfect location for the outdoor explorer
9.8 out of 10, Exceptional, (8)
"Perfect location friendly accommodating hosts!"
United States
steven s.
The price is HK$1,163
HK$2,375 total
includes taxes & fees
7 Jan - 8 Jan
Charming studio apartment - Perfect location for the outdoor explorer
Fridge, microwave, oven, stovetop
Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.

Holiday Home in Sheboygan

Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.
10.0 out of 10, Exceptional, (12)
"Everything was clean and spacious. Had a great time and would definitely stay again! "
United States
Brad T.
The price is HK$3,261
HK$6,042 total
includes taxes & fees
5 Jan - 6 Jan
Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.
Exterior
Edgewater Villa: 4 Bedroom, Sleeps 14!

Condo in Sheboygan

Edgewater Villa: 4 Bedroom, Sleeps 14!
2.0 star property
8.6 out of 10, Excellent, (12)
"Nice property, close to the beach. It was perfect for our weekend getaway. "
United States
Rebecca B.
The price is HK$2,296
HK$4,882 total
includes taxes & fees
3 Jan - 4 Jan
Edgewater Villa: 4 Bedroom, Sleeps 14!
Beach
Hot Tub, Fire Pit, Point Beach & Neshotah Beach

Holiday Home in Two Rivers

Hot Tub, Fire Pit, Point Beach & Neshotah Beach
2.0 star property
Hot Tub, Fire Pit, Point Beach & Neshotah Beach
Terrace/patio
Brand new Modern, 6 bedroom waterfront home on a beautiful Long Lake.

Holiday Home in Campbellsport

Brand new Modern, 6 bedroom waterfront home on a beautiful Long Lake.
2.0 star property
The price is HK$6,220
HK$10,405 total
includes taxes & fees
4 Jan - 5 Jan
Brand new Modern, 6 bedroom waterfront home on a beautiful Long Lake.
Fridge, microwave, oven, stovetop
Cate's Place: Charming home just minutes from Ice Age Trail & Neshotah Beach

Holiday Home in Two Rivers

Cate's Place: Charming home just minutes from Ice Age Trail & Neshotah Beach
9.8 out of 10, Exceptional, (37)
"House worked well for what we needed. Will look to book again if in the area another time. "
United States
Jodi S.
The price is HK$1,646
HK$2,107 total
includes taxes & fees
3 Jan - 4 Jan
Cate's Place: Charming home just minutes from Ice Age Trail & Neshotah Beach
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

Comfort Inn & Suites Sheboygan I-43

Comfort Inn & Suites Sheboygan I-43

10/10 Excellent
"Hot tub was great. Beds were very comfortable "
susan 2-night trip
Posted 4 days ago
Comfort Inn & Suites Sheboygan I-43

Find out more about Sheboygan

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 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 holiday rentals that Sheboygan has to offer?

Lake Michigan Home with gorgeous views, great spot for family or golf retreat: 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. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals will I find in Sheboygan?

Choose from 97 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 Bookworm Gardens, 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 Kohler Park Dunes State Natural Area 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.