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Sheboygan Holiday Rentals

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Check prices for these dates

Tonight
31 Dec - 1 Jan
Tomorrow
1 Jan - 2 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Sheboygan holiday rentals

Terrace/patio
Victorian Inn Elkhart Lake Wisconsin

Aparthotel in Elkhart Lake

Victorian Inn Elkhart Lake Wisconsin
4.0 star property
8.8 out of 10, Excellent, (3)
"Perfect location, great amenities."
United States
Deirdre
Victorian Inn Elkhart Lake Wisconsin
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$971
HK$1,102 total
includes taxes & fees
1 Jan - 2 Jan 2026
Grandstay Residential Suites Hotel - Sheboygan
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$1,143
HK$3,130 total
includes taxes & fees
3 Jan - 4 Jan 2026
Large Backyard, Walk to Hospital: Sheboygan Abode!
Bar (on property)
First Floor Pet Friendly Queen Suite with Single Pull-out

Villa in Elkhart Lake

First Floor Pet Friendly Queen Suite with Single Pull-out
10.0 out of 10, Exceptional, (2)
"So convenient to all things Elkhart Lake. Great accommodations and host. Would highly recommend!"
United States
Brenda H.
First Floor Pet Friendly Queen Suite with Single Pull-out
Exterior
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Holiday Home in Oostburg

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
10.0 out of 10, Exceptional, (116)
"We loved the cozy cottage and cuddled up with books under the afghans on the cool evenings. The lake was a pleasant walk away."
United States
bev w.
The price is HK$933
HK$1,148 total
includes taxes & fees
12 Jan - 13 Jan 2026
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
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$1,015 total
includes taxes & fees
4 Jan - 5 Jan 2026
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
3 bedrooms, iron/ironing board, WiFi, bed sheets
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

Apartment in Sheboygan

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
10.0 out of 10, Exceptional, (4)
"Very clean and good location; nice place for our dog; we would definitely stay again if the opportunity presents itself."
United States
Stephanie K.
The price is HK$700
HK$1,324 total
includes taxes & fees
11 Jan - 12 Jan 2026
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Smart TV
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Apartment in Sheboygan

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
9.2 out of 10, Wonderful, (10)
"Coastal Comfort was very clean, pleasantly decorated and comfortable. It is within driving distance to the lake as well as restaurants in Sheboygan. Perfect stay for the two of us. "
United States
Kim K.
The price is HK$630
HK$1,245 total
includes taxes & fees
4 Jan - 5 Jan 2026
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Exterior
Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater

Holiday Home in Fond du Lac

Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater
4.0 star property
10.0 out of 10, Exceptional, (1)
"Our large family had a magical Christmas! Our beautifully decorated rented home had everything we needed . We were all very comfortable during the day and night time sleeping . We had private spaces and family get together areas ."
United States
Brenda J.
The price is HK$13,993
HK$25,147 total
includes taxes & fees
7 Jan - 8 Jan 2026
Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater
Indoor pool, a heated pool
Modern Room Near Indoor Pool

Villa in Elkhart Lake

Modern Room Near Indoor Pool
9.6 out of 10, Exceptional, (4)
"Our host was extremely responsive and resourceful. The room was very clean and nice. "
United Kingdom
Brandon B.
Modern Room Near Indoor Pool
Exterior detail
Logan Ave Holiday House - Upper

Apartment in Sheboygan

Logan Ave Holiday House - Upper
9.4 out of 10, Exceptional, (3)
"We had a great stay here during the boat races. The host was so nice and left us local cheese & beer to welcome us to the house/city. We would definitely stay here again!"
United States
MELISSA C.
The price is HK$700
HK$2,296 total
includes taxes & fees
2 Jan - 3 Jan 2026
Logan Ave Holiday House - Upper
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
The price is HK$840
HK$3,387 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hot Tub, Fire Pit, Point Beach & Neshotah Beach
Property grounds
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan

Apartment in Sheboygan

Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
10.0 out of 10, Exceptional, (1)
"In town for family celebration. This was a convenient location to my parent’s home! Thanks!"
United States
Shelly E.
The price is HK$630
HK$1,244 total
includes taxes & fees
4 Jan - 5 Jan 2026
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
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$894
HK$1,191 total
includes taxes & fees
31 Jan - 1 Feb 2026
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
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$1,161
HK$2,372 total
includes taxes & fees
5 Jan - 6 Jan 2026
Charming studio apartment - Perfect location for the outdoor explorer
Living area
2nd floor loft near the lake!

Apartment in Manitowoc

2nd floor loft near the lake!
9.8 out of 10, Exceptional, (15)
"Very clean, and tastefully decorated…would rent again:)"
United States
Kim B.
The price is HK$1,015
HK$1,753 total
includes taxes & fees
4 Jan - 5 Jan 2026
2nd floor loft near the lake!
Smart TV, books, music library
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Apartment in Downtown Sheboygan

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
9.8 out of 10, Exceptional, (9)
"The flat is gorgeous and in a fantastic location. "
United States
Sarah G.
The price is HK$665
HK$1,857 total
includes taxes & fees
11 Jan - 12 Jan 2026
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
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$1,244
HK$6,028 total
includes taxes & fees
1 Jan - 2 Jan 2026
Cabin on Lake 75 Acre Lake: Couples Get Away or Fun Family Vacation
Fridge, microwave, oven, stovetop
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

Holiday Home in Sheboygan

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
9.8 out of 10, Exceptional, (255)
"Beautiful view and perfect for our Wisconsin lake getaway."
United States
Holly A.
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Fridge, microwave, oven, stovetop
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

Holiday Home in Sheboygan

Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
10.0 out of 10, Exceptional, (6)
"4 forever friends getaway. Relaxation, eats and drinks with a little antique and thrift shopping"
United States
Stacy P.
The price is HK$840
HK$1,484 total
includes taxes & fees
21 Jan - 22 Jan 2026
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
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 1 day 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?

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 air conditioning 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. Some other homes for rent in Sheboygan include Lake Michigan Home with gorgeous views, great spot for family or golf retreat and Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX.

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 Kohler Park Dunes State Natural Area, 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-Andrae State Park 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.