Vacation rentals in Sheboygan - HomeToGo base64Hash Vacation rentals in Sheboygan - HomeToGo

Vacation rentals in Sheboygan

Browse 431 available vacation homes and compared across 7 trusted partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • House
    • Apartment
    • Farmhouse

  • Distance to center

    • 2 mi
    • 3 mi
    • Any

  • Rating

    • 4.5+
    • 4+

  • Booking Options

    • Instant Booking

  • Services

    • Pool
    • WiFi
    • Air conditioning
    • Kitchen
    • TV
    • Microwave
    • Washing machine
    • Balcony/patio
    • Parking
    • Hot tub
    • Dishwasher
    • Fireplace
    • Yard
    • Crib
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • Wheelchair access
    • No pets

  • Activities

    • Grill
    • Fishing

Top 15 most Recommended Vacation Rentals in Sheboygan

Discover your ideal Sheboygan vacation rental with real-time comparisons of 431 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Apartment Sheboygan
Apartment ∙ 7 guests ∙ 2 bedrooms

Holiday apartment | Water view

Sheboygan, Sheboygan County, Wisconsin, United States
This waterfront apartment at South Pier offers a kitchen, fireplace, balcony, and beach access with stunning sea views for seven guests.
from $218
per night
Excellent(17 ratings)
from $218
per night
View deal
Villa Sheboygan
Villa ∙ 12 guests ∙ 4 bedrooms

Villa | Lake view

Sheboygan, Sheboygan County, Wisconsin, United States
This waterfront villa at South Pier offers a kitchen, fireplace, and beach access, perfect for a memorable family getaway.
from $315
per night
Outstanding(119 ratings)
from $315
per night
View deal
House Sheboygan
House ∙ 14 guests ∙ 5 bedrooms

Vacation home with patio, yard & grill | Lake view | Good for workation

Sheboygan, Sheboygan County, Wisconsin, United States
This house rental in Roosevelt Park features a fireplace, kitchen, and balcony, perfect for family gatherings by the waterfront.
from $552
per night
Outstanding(154 ratings)
from $552
per night
View deal
Cabin Sheboygan
Cabin ∙ 2 guests ∙ 1 bedroom

Cottage with barbecue, yard & patio | Nature view

Sheboygan, Sheboygan County, Wisconsin, United States
This waterfront cabin in Sheboygan features a kitchen, fireplace, and beach access, perfect for a cozy getaway for two.
from $216
per night
Outstanding(304 ratings)
from $216
per night
View deal
Condo Sheboygan
Condo ∙ 4 guests ∙ 2 bedrooms

Fully equipped condo with terrace | Lake view | Beach nearby

Sheboygan, Sheboygan County, Wisconsin, United States
This waterfront condo in King Park features a kitchen and parking, perfect for a getaway with friends or family of four.
from $106
per night
Outstanding(42 ratings)
from $106
per night
View deal
House Sheboygan
House ∙ 9 guests ∙ 4 bedrooms

Family-friendly beautiful vacation home with patio, grill & garden | City view | Beach nearby

Sheboygan, Sheboygan County, Wisconsin, United States
This house rental in the Ellis Historical District features a fireplace, kitchen, and yard, accommodating up to 9 guests.
from $301
per night
Outstanding(90 ratings)
from $301
per night
View deal
House Sheboygan
House ∙ 16 guests ∙ 7 bedrooms

Family-friendly charming vacation home with barbeque, garden & private pool | Good for workation

Sheboygan, Sheboygan County, Wisconsin, United States
This Sheboygan house rental features a private heated pool, hot tub, and ample space for 16 guests to create unforgettable memories.
from $1,269
per night
Outstanding(9 ratings)
from $1,269
per night
View deal
House Sheboygan
House ∙ 10 guests ∙ 3 bedrooms

Child-friendly vacation home with grill | Close to the beach

Sheboygan, Sheboygan County, Wisconsin, United States
This house rental in King Park features a kitchen, parking, and ample space for 10, making it perfect for family getaways.
from $155
per night
Outstanding(24 ratings)
from $155
per night
View deal
Condo Sheboygan
Condo ∙ 8 guests ∙ 2 bedrooms

Condo with 2 rooms for 8 persons

Sheboygan, Sheboygan County, Wisconsin, United States
This South Pier condo features a kitchen and comfortably accommodates up to 8 guests, perfect for your next getaway.
from $93
per night
Outstanding(33 ratings)
from $93
per night
View deal
House Sheboygan
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped house with barbeque | Beach nearby

Sheboygan, Sheboygan County, Wisconsin, United States
This house rental in Farnsworth features a kitchen, balcony, and parking for 8 guests, perfect for your next getaway.
from $175
per night
Outstanding(7 ratings)
from $175
per night
View deal
Apartment Sheboygan
Apartment ∙ 5 guests ∙ 2 bedrooms

Apartment with 2 rooms for 5 persons

Sheboygan, Sheboygan County, Wisconsin, United States
This apartment in Roosevelt Park features a kitchen, balcony, beach access, and parking, comfortably accommodating five guests.
from $327
per night
Outstanding(9 ratings)
from $327
per night
View deal
House Sheboygan
House ∙ 10 guests ∙ 4 bedrooms

House with patio

Sheboygan, Sheboygan County, Wisconsin, United States
This spacious house rental in Sheboygan accommodates 10, features a kitchen, allows pets, and includes convenient parking.
from $352
per night
Outstanding(76 ratings)
from $352
per night
View deal
House Sheboygan
House ∙ 8 guests ∙ 4 bedrooms

Family-oriented spacious vacation home with grill | Good for workation

Sheboygan, Sheboygan County, Wisconsin, United States
This waterfront house rental in Sheboygan offers a kitchen, parking, and space for 8, perfect for family getaways.
from $301
per night
Outstanding(47 ratings)
from $301
per night
View deal
House Sheboygan
House ∙ 5 guests ∙ 2 bedrooms

Family-friendly pleasant house with hot tub, yard & BBQ | Pet-friendly

Sheboygan, Sheboygan County, Wisconsin, United States
This family-friendly house in Sheboygan features a kitchen, yard, hot tub, and a cozy fireplace, perfect for your getaway.
from $183
per night
Outstanding(222 ratings)
from $183
per night
View deal
House Sheboygan
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented spacious house with terrace, yard & barbeque | Nature view | Beach nearby | Pets are welcome

Sheboygan, Sheboygan County, Wisconsin, United States
This Sheboygan house rental for six features a kitchen, yard, and parking, plus it's perfect for families and pets.
from $197
per night
Outstanding(104 ratings)
from $197
per night
View deal

Vacation Houses With Pools

Aparthotel Sheboygan
from $160
per night
Aparthotel ∙ 4 guests ∙ 1 bedroom

Aparthotel with pool, terrace & barbecue | Good for workation

4.3
Very good(912 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
Pool
View deal
Aparthotel Sheboygan
from $135
per night
Aparthotel ∙ 3 guests ∙ 1 bedroom

Fully equipped aparthotel with pool, patio & barbecue | Suitable for remote work

4.3
Very good(912 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
Pool
View deal
Aparthotel Sheboygan
from $134
per night
Aparthotel ∙ 4 guests ∙ 1 bedroom

Aparthotel with pool, BBQ & terrace | Suitable for remote work

4.3
Very good(912 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
Pool
View deal
See all offers

Dog-Friendly Vacation Rentals

House Sheboygan
from $263
per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with patio

5.0
Outstanding(76 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
Pet-friendly
View deal
House Sheboygan
from $162
per night
House ∙ 11 guests ∙ 4 bedrooms

Children-friendly house with grill | Pets are welcome

5.0
Outstanding(36 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
Pet-friendly
View deal
House Sheboygan
from $137
per night
House ∙ 6 guests ∙ 2 bedrooms

House with patio & yard

5.0
Outstanding(7 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
Pet-friendly
View deal
See all offers

Vacation rentals with a balcony

House Sheboygan
from $133
per night
House ∙ 7 guests ∙ 3 bedrooms

House with patio, barbeque & garden | Lake view

4.9
Outstanding(173 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
Balcony
View deal
House Sheboygan
from $1,739
per night
House ∙ 24 guests ∙ 10 bedrooms

House with jacuzzi, terrace & garden | City view | Suitable for remote work

4.9
Outstanding(94 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
Balcony
View deal
House Sheboygan
from $166
per night
House ∙ 6 guests ∙ 2 bedrooms

Vacation home with terrace | Lake view

4.9
Outstanding(290 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
Balcony
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Sheboygan offering exceptional value for money

House Sheboygan
from $185
per night
House ∙ 6 guests ∙ 2 bedrooms

Family-friendly house with garden | Pets allowed

Sheboygan, Sheboygan County, Wisconsin, United States
View deal
House Sheboygan
from $214
per night
House ∙ 12 guests ∙ 4 bedrooms

Child-friendly vacation home with barbecue & yard | City view | Beach nearby | Suitable for remote work

4.9
Outstanding(15 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
View deal
Condo Sheboygan
from $179
per night
Condo ∙ 7 guests ∙ 2 bedrooms

Family-friendly condo | Next to the beach | Good for workation

4.7
Excellent(60 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
View deal

Top-Rated Vacation rentals in Sheboygan

Book the highest-rated Sheboygan vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Condo Sheboygan
from $213
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Children-friendly condo | Suitable for remote work

5.0
Outstanding(48 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
View deal
House Sheboygan
from $616
per night
House ∙ 9 guests ∙ 4 bedrooms

Child-friendly charming house with garden, terrace & grill | City view | Next to the beach | Perfect for remote work

4.9
Outstanding(47 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
View deal
Condo Sheboygan
from $52
per night
Condo ∙ 8 guests ∙ 2 bedrooms

Fully equipped condo with terrace | Close to the beach

4.8
Outstanding(47 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
View deal

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Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

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Spend your budget exactly as planned by comparing thousands of providers.

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Find your dream stay

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Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Features & Amenities in Sheboygan

  • Pet-friendly (139)
  • Pool (173)
  • WiFi (425)
  • Air conditioning (428)
  • Kitchen (217)
  • TV (392)
  • Microwave (345)
  • Grill (94)
  • Washing machine (216)
  • Balcony/patio (76)
  • Parking (17)
  • Hot tub (24)

Sheboygan is a great vacation destination if you want an accommodation with a pool, as 40% of the accommodations provide one. Additionally, more House rental have pools than any other accommodation type. They are a great choice if you go in a group of 11, as that is the number of people they can welcome on average. If you would ideally like to be close to the water, two-thirds of the accommodations with a pool are within 2 miles of the waterfront.

Information about vacation rentals in Sheboygan

🏡 Vacation rentals available 431 rentals
💳 Possible discounts up to 13%
🌙 Nightly prices starting at $26
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 137 homes
🏊 Vacation rentals with pools 173 homes

Frequently Asked Questions

What is the nightly price for a vacation rental in Sheboygan?

The price of a night's stay in Sheboygan starts at $26. Nightly prices for house rentals are $698 on average. Apartment rentals in Sheboygan cost on average $306 per night.

How many vacation homes are available for booking in Sheboygan?

There are currently 431 vacation homes from 7 providers in Sheboygan.

What are the most popular amenities for vacation homes in Sheboygan?

Usually travelers look for Pool, Pets allowed, and Internet when booking a vacation rental in Sheboygan.

How many vacation rentals with pools are in Sheboygan?

Check out 173 vacation rentals available to book in Sheboygan.

Are dogs allowed in vacation homes in Sheboygan?

Absolutely, currently there are 137 rentals in Sheboygan that allow dogs , with an average nightly rate of $308.

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