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

Vacation rentals in Sheboygan

Browse 343 available vacation homes and compared across 6 trusted partners
Anytime
Guests
Anytime
Guests

  • Price per night

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

  • Accommodation types

    • House
    • Apartment
    • Farmhouse

  • Distance to center

    • 1 mi
    • 2 mi
    • 3 mi

  • Rating

    • 4.5+
    • 4+

  • Popular amenities

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

  • Other Services

    • 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 365 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Villa Sheboygan
Villa ∙ 12 guests ∙ 4 bedrooms

Villa with hot tub | 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 $372
per night
Outstanding(138 ratings)
from $372
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 $243
per night
Excellent(9 ratings)
from $243
per night
View deal
House Sheboygan
House ∙ 10 guests ∙ 5 bedrooms

House with patio, yard & hot tub | City view | Suitable for remote work

Sheboygan, Sheboygan County, Wisconsin, United States
This waterfront house in Sheboygan features a kitchen, fireplace, and yard, accommodating up to 10 guests for a perfect getaway.
from $176
per night
Outstanding(23 ratings)
from $176
per night
View deal
House Sheboygan
House ∙ 11 guests ∙ 4 bedrooms

Children-friendly house with grill | Pets are welcome

Sheboygan, Sheboygan County, Wisconsin, United States
This house rental in Gateway accommodates 11 guests, featuring a kitchen, parking, and a pet-friendly environment for families.
from $283
per night
Outstanding(48 ratings)
from $283
per night
View deal
House Sheboygan
House ∙ 12 guests ∙ 4 bedrooms

Vacation home with barbecue | Beach nearby

Sheboygan, Sheboygan County, Wisconsin, United States
This Sheboygan house rental features a kitchen and accommodates up to 12 guests, perfect for your next group getaway.
from $677
per night
Outstanding(5 ratings)
from $677
per night
View deal
House Sheboygan
House ∙ 16 guests ∙ 7 bedrooms

Family-friendly charming vacation home with barbeque, garden & private pool | Nature view | 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 $1,686
per night
Outstanding(15 ratings)
from $1,686
per night
View deal
House Sheboygan
House ∙ 12 guests ∙ 5 bedrooms

House with patio & BBQ | Good for workation

Sheboygan, Sheboygan County, Wisconsin, United States
This house rental on South Pier offers a fireplace, kitchen, balcony, and parking for up to 12 guests, perfect for family gatherings.
from $270
per night
Outstanding(10 ratings)
from $270
per night
View deal
House Sheboygan
House ∙ 9 guests ∙ 3 bedrooms

Child-friendly lovely house with grill & garden | Lake view | Close to the beach

Sheboygan, Sheboygan County, Wisconsin, United States
This Sheboygan house rental offers a kitchen, yard, and waterfront views, perfect for family stays of up to 9 guests.
from $449
per night
Outstanding(30 ratings)
from $449
per night
View deal
Condo Sheboygan
Condo ∙ 14 guests ∙ 4 bedrooms

Condo with terrace | Lake view

Sheboygan, Sheboygan County, Wisconsin, United States
This waterfront condo on South Pier features a fireplace, kitchen, balcony, and parking, accommodating up to 14 guests.
from $453
per night
Good(10 ratings)
from $453
per night
View deal
House Sheboygan
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with patio, yard & jacuzzi | Lake view

Sheboygan, Sheboygan County, Wisconsin, United States
This Sheboygan house rental offers a kitchen, a yard, waterfront views, and parking for up to 10 guests.
from $413
per night
Outstanding(11 ratings)
from $413
per night
View deal
House Sheboygan
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with patio

Sheboygan, Sheboygan County, Wisconsin, United States
This Sheboygan house rental offers a kitchen, parking, and space for 10, making it perfect for family and pet-friendly getaways.
from $478
per night
Outstanding(25 ratings)
from $478
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 $633
per night
Outstanding(155 ratings)
from $633
per night
View deal
House Sheboygan
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped lovely house with barbeque, yard & terrace | Close to the beach

Sheboygan, Sheboygan County, Wisconsin, United States
This North Point house rental offers a fireplace, kitchen, yard, and parking, perfect for up to 8 guests seeking adventure.
from $434
per night
Outstanding(34 ratings)
from $434
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 $204
per night
Outstanding(109 ratings)
from $204
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 $323
per night
Outstanding(93 ratings)
from $323
per night
View deal

Dog-Friendly Vacation Rentals

Apartment Sheboygan
from $132
per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Holiday apartment with garden | Lake view | Perfect for remote work

4.7
Excellent(13 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
Pet-friendly
View deal
House Sheboygan
from $337
per night
House ∙ 8 guests ∙ 4 bedrooms

House | Perfect for remote work

5.0
Outstanding(18 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
Pet-friendly
View deal
Apartment Sheboygan
from $157
per night
Apartment ∙ 5 guests ∙ 3 bedrooms

Holiday apartment with barbecue | Suitable for remote work

4.8
Outstanding(20 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
Pet-friendly
View deal
See all offers

Vacation Houses With Pools

Aparthotel Sheboygan
from $165
per night
Aparthotel ∙ 6 guests ∙ 1 bedroom

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

4.3
Very good(1062 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
Pool
View deal
Aparthotel Sheboygan
from $136
per night
Aparthotel ∙ 3 guests ∙ 1 bedroom

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

4.3
Very good(1062 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
Pool
View deal
Resort Sheboygan
from $274
per night
Resort ∙ 2 guests ∙ 1 bedroom

Resort with jacuzzi & pool | City view

4.2
Very good(473 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
Pool
View deal
See all offers

Vacation rentals and apartments with air conditioning

House Sheboygan
from $194
per night
House ∙ 8 guests ∙ 4 bedrooms

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

4.9
Outstanding(56 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
Air conditioning
View deal
House Sheboygan
from $293
per night
House ∙ 7 guests ∙ 3 bedrooms

Vacation home with yard & barbeque

5.0
Outstanding(19 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
Air conditioning
View deal
Cabin Sheboygan
from $241
per night
Cabin ∙ 7 guests ∙ 2 bedrooms

Fully equipped nice cottage with BBQ | Good for workation

Sheboygan, Sheboygan County, Wisconsin, United States
Air conditioning
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Sheboygan offering exceptional value for money

Condo Sheboygan
from $451
per night
Condo ∙ 6 guests ∙ 3 bedrooms

Fully equipped ample condo with patio | Next to the beach | Perfect for remote work

Sheboygan, Sheboygan County, Wisconsin, United States
View deal
House Sheboygan
from $296
per night
House ∙ 9 guests ∙ 3 bedrooms

Vacation home with yard, terrace & BBQ | City view | Perfect for remote work

5.0
Outstanding(28 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
View deal
Apartment Sheboygan
from $128
per night
Apartment ∙ 5 guests ∙ 2 bedrooms

Children-friendly apartment with yard & terrace | Perfect for remote work

5.0
Outstanding(3 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 $251
per night
Condo ∙ 7 guests ∙ 3 bedrooms

Condo with terrace & hot tub | City view

5.0
Outstanding(157 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
View deal
House Sheboygan
from $292
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with terrace, barbecue & garden | City view | Perfect for remote work

4.9
Outstanding(33 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
View deal
Apartment Sheboygan
from $230
per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Rental apartment with yard & terrace

5.0
Outstanding(11 ratings)
Sheboygan, Sheboygan County, Wisconsin, United States
View deal

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

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Popular Features & Amenities in Sheboygan

  • Pet-friendly (139)
  • Pool (173)
  • WiFi (424)
  • Air conditioning (426)
  • Kitchen (215)
  • TV (390)
  • Microwave (344)
  • Grill (94)
  • Washing machine (215)
  • 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 14, as that is the number of people they can welcome on average. If you would ideally like to be close to the water, more than two-thirds of the accommodations with a pool are within 2 miles of the waterfront.

Information about vacation rentals in Sheboygan

🏡 Vacation rentals available 343 rentals
💳 Possible discounts up to 13%
🌙 Nightly prices starting at $113
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 80 homes
🏊 Vacation rentals with pools 136 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 $113. Nightly prices for house rentals are $659 on average. Condos in Sheboygan cost on average $541 per night.

How many vacation homes are available for booking in Sheboygan?

There are currently 343 vacation homes from 6 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 136 vacation rentals available to book in Sheboygan.

Are dogs allowed in vacation homes in Sheboygan?

Absolutely, currently there are 80 rentals in Sheboygan that allow dogs , with an average nightly rate of $304.

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