Sheboygan vacation rentals

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Top-rated vacation rentals in Sheboygan

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Oostburg

4.97 out of 5 average rating, 231 reviews

Sandalwood Cottage - 300 Feet From Lake Michigan

A HIDEAWAY one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan, on a private drive. Just South of Sheboygan. Close by: Whistling Straits & PGA golf courses. Ice Age Trail in the Kettle Moraine, Elkhart Lake - Road America, Charter Fishing, Kohler Andrae State Park, Several State & local beaches, & several 5 star restaurants. 2 hours & 20 min from Chicago. 45 min from Milwaukee, 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.

Oct 31 – Nov 7

G$33,033 GYD per night

Guest favorite

Home in Howards Grove

4.95 out of 5 average rating, 151 reviews

Spacious lower level priv entrance no cleaning fee

Entire basement is for rent with a separate entrance. Kitchen area includes refrigerator, microwave, coffee pot, toaster, sink, dining table and chairs. NO STOVE OR OVEN IS AVAILABLE. Free Wifi and Cable TV. Air conditioning. Plenty of parking, keyless entry. 14 min to Road America, 13 min to Kohler, 9 min to Whistling Straits, 5 min to Lakeland University, 1 hr to Milwaukee, 1 hr to Green Bay. Lots of nice amenities, clean, spacious. No cleaning fee. Unit NOT set up for babies or toddlers.

Apr 30 – May 7

G$22,646 GYD per night

Guest favorite

Townhouse in Sheboygan

4.97 out of 5 average rating, 117 reviews

Family Friendly Riverfront Escape|HUGE Game Room

Welcome to The WAVE – your ideal family friendly retreat nestled along the scenic Sheboygan River, just minutes from the beaches of Lake Michigan. As you step into The WAVE, you'll be greeted by a tastefully designed interior featuring LUX furnishings that exude both style and coziness. The accommodations include a King Suite with a riverfront balcony and a Guest Room with 2 queen beds. Entertainment is taken to a whole new level with our 500 sq ft game room with a 130-inch projection screen.

Oct 24 – 31

G$25,457 GYD per night

Guest favorite

Home in Sheboygan

4.83 out of 5 average rating, 150 reviews

Home Away From Home-One Block From Lake Michigan!

Amazing location close to all things beautiful in this spacious centrally-located pet friendly home. YouTube “Sheboygan AirBnb” to watch a thorough walkthrough! Walking distance from the beach, parks, downtown 8th street, also many golf courses nearby including Whistling Straights, multiple boat ramps, 16 miles from Road America, and so much more! Multiple room configurations available, pet friendly, fully fenced back yard, lots of parking, driveway should be able to fit most boats.

Nov 30 – Dec 7

G$34,887 GYD per night

Guest favorite

Home in Sheboygan

4.97 out of 5 average rating, 151 reviews

Logan's Guest Nest

Logan's Guest Nest is located in a nice small town feel area. With a small look on the outside your Nest has a big feel on the inside. Spacious rooms and quiet area to rest after a day at the many beaches lining Lake Michigan. Or coming back from the races at Road America. Not to mention a day of golf at the many area courses, Whistling Straits maybe. All these wonderful outings are just minutes from the Nest. Plenty of local dinning or delivery for a nice ending of the day.

Jun 19 – 26

G$32,965 GYD per night

Guest favorite

Apartment in Sheboygan

4.92 out of 5 average rating, 394 reviews

Cozy Sheboygan Upper

We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.

Jan 2 – 9

G$17,163 GYD per night

Guest favorite

Condo in Sheboygan

4.87 out of 5 average rating, 192 reviews

Beachside Lake View - 2br - First Floor - Garage

Located just one lot in from the beautiful shores or Lake Michigan. Amazing location provides year round stunning views . This is a lower 2 bedroom 1 bath condo in a 4unit building were all the units have the same basic layout. You can listen to the waves or walk just a few feet and have the sand on your feet. This condo features front and rear balconies. Makes for a great place to enjoy a weekend get away or a place to relax at night while on a business trip.

Mar 7 – 14

G$30,709 GYD per night

Guest favorite

Home in Sheboygan

4.94 out of 5 average rating, 171 reviews

Beachfront getaway in Sheboygan

One of the few homes in Sheboygan that walks out onto the sands of Lake Michigan, this 3 bedroom/ 2 bath home is meant for total relaxation and fun. The open kitchen, dining and living room is full of light from the sliding glass doors on the back of the house, which access a deck and a large back yard. Upstairs is a spacious loft with a pull out couch. Fire pit in the back yard. Just steps from a playground at King Park. Amazing sunrises, worth waking up for.

Oct 23 – 30

G$54,353 GYD per night

Guest favorite

Apartment in Sheboygan

4.84 out of 5 average rating, 183 reviews

Sheboygan Surf House "Jetties"

Located just 24 steps above Wisconsin's first Surf Shop, EOS Surf. Our Urban living oasis is a fully equipped studio apartment conveniently located in the heart of downtown, just steps from bars and restaurants and only blocks to Lake Michigan South Pier and Blue Harbor. Whether you are here for adventure sports like Surfing on the Great Lake, Kite boarding, charter fishing, a Wedding or leisure time SSH is perfect for you. Support Dog friendly

Dec 8 – 15

G$11,823 GYD per night

Guest favorite

Guesthouse in Sheboygan

4.83 out of 5 average rating, 367 reviews

Carriage House Sheboygan, Lake Mich beach access!

The Carriage House is the perfect getaway. Located in a beautiful historic neighborhood with Lake Michigan public beach access across the street, 100 yards away. Ideal for a family of four or an individual in town for business. Amenities have been thoughtfully placed to create the most comfortable and convenient stay for guests. We pride ourselves on ensuring you enjoy your stay with us and guarantee you'll love the neighborhood!

Feb 12 – 19

G$29,679 GYD per night

Guest favorite

Home in Sheboygan

4.97 out of 5 average rating, 115 reviews

Lake Michigan home with gorgeous views!

Our beautiful lakefront home is perfect for bringing everyone together - Ladies weekend, guys golf trip, family reunion, Packers games...this is your place. Minutes to downtown Sheboygan/Kohler, with 5 star PGA championship golf courses (Black Wolf Run, Whistling Straits, The Bull of Pinehurst), Kohler Waters Spa, and the beaches/dunes of Kohler Andrae State Park. Renovated bedroom and movie room completed early 2020.

Jan 30 – Feb 6

G$106,554 GYD per night

Guest favorite

Apartment in Sheboygan

4.89 out of 5 average rating, 270 reviews

Spiritual Vibes Downtown Walk-up

New art and hand crafted decor. Some are even available for purchase, others are for guests to enjoy during their stay. Cozy, inviting, private apartment close to restaurants, shops and entertainment. Wonderful morning and evening light. Large deck for relaxing outdoors or enjoying the sun. We have a storage shed for bikes, strollers and the like if needed. Just give us the heads up and we'll give you the key.

Mar 19 – 26

G$19,246 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Sheboygan vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Sheboygan's top sights

Blue Harbor Resort27 locals recommend

Bookworm Gardens31 locals recommend

Black Pig19 locals recommend

Parker John's BBQ & Pizza - Sheboygan22 locals recommend

Texas Roadhouse3 locals recommend

Deland Park22 locals recommend

Other great vacation rentals in Sheboygan

Guest favorite

Apartment in Waldo

4.98 out of 5 average rating, 258 reviews

The Blue Cobb House

Dec 22 – 29

G$22,289 GYD per night

Superhost

Apartment in Sheboygan

4.84 out of 5 average rating, 63 reviews

The Beach | Sheboygan 2Br/1 Ba

Nov 21 – 28

G$25,275 GYD per night

Guest favorite

Guest suite in Sheboygan

4.92 out of 5 average rating, 66 reviews

Cozy 1BD RM W/ fireplace by lake

May 8 – 15

G$20,381 GYD per night

Guest favorite

Apartment in Sheboygan

4.88 out of 5 average rating, 48 reviews

One Bdrm Apt - The Erie House near lake & downtown

Jun 9 – 16

G$19,304 GYD per night

Guest favorite

Apartment in Sheboygan

4.98 out of 5 average rating, 89 reviews

Lovely modern two bedroom home with fire pit

Dec 6 – 13

G$27,033 GYD per night

Guest favorite

Townhouse in Sheboygan

4.94 out of 5 average rating, 81 reviews

Danz Sheboygan Retreat. Newly Remodeled in 2021.

Nov 5 – 12

G$20,515 GYD per night

Guest favorite

Apartment in Sheboygan

5.0 out of 5 average rating, 36 reviews

Quaint Blast from the Past - walk to lake/8th st

Oct 21 – 28

G$27,290 GYD per night

Guest favorite

Home in Sheboygan

4.91 out of 5 average rating, 69 reviews

Spacious MCM Vibe Near Lake MI w/ Fire Pit

Nov 7 – 14

G$26,864 GYD per night

Show all

Other great vacation rentals in Sheboygan

Guest favorite

Home in Sheboygan

4.94 out of 5 average rating, 54 reviews

ClaraVida - Cheerful 1 Bed/2 Bath Near Beach

Oct 26 – Nov 2

G$29,554 GYD per night

Guest favorite

Apartment in Sheboygan

5.0 out of 5 average rating, 87 reviews

Modern Upstairs Apt - Steps from Lake Michigan

Feb 27 – Mar 6

G$27,582 GYD per night

Superhost

Apartment in Sheboygan

4.9 out of 5 average rating, 49 reviews

Lovely 1 Bedroom Serviced apartment in Sheboygan

Sep 7 – 14

G$24,030 GYD per night

Guest favorite

Home in Sheboygan

4.94 out of 5 average rating, 17 reviews

House on a quiet street w/ off street parking 3bdr

May 9 – 16

G$24,112 GYD per night

Guest favorite

Home in Sheboygan

5.0 out of 5 average rating, 63 reviews

Relaxing Sheboygan/Kohler Getaway

Aug 26 – Sep 2

G$29,525 GYD per night

Guest favorite

Home in Sheboygan

5.0 out of 5 average rating, 14 reviews

The perfect location!

Dec 13 – 20

G$25,809 GYD per night

Guest favorite

Apartment in Sheboygan

4.96 out of 5 average rating, 27 reviews

North 7th Place - Entire Unit- 2 bedrooms

Jun 16 – 23

G$30,314 GYD per night

Guest favorite

Apartment in Sheboygan

4.95 out of 5 average rating, 20 reviews

Peaceful apartment by the lake

Jan 30 – Feb 6

G$25,094 GYD per night

Show all

Quick stats about vacation rentals in Sheboygan

Total rentals
250 properties
Rentals with dedicated workspaces
130 properties have a dedicated workspace
Pet-friendly rentals
70 properties allow pets
Family-friendly rentals
200 properties are a good fit for families
Total number of reviews
9.4K reviews
Nightly prices starting at
G$4,178 GYD before taxes and fees

Frequently Asked Questions

Where should I stay in Sheboygan?
Make yourself at home in Sheboygan by choosing from our most frequently booked neighborhoods. We have over 200 vacation rentals in James Madison, over 200 vacation rentals in Business Drive North, and over 260 vacation rentals in End Park.
Are there vacation rentals with a dedicated workspace in Sheboygan?
Yes! Work meets play with ease at over 130 vacation rentals in Sheboygan featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Sheboygan?
Four-legged friends are welcome in Sheboygan. Choose from more than 70 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Sheboygan?
Experience the best of Sheboygan with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Sheboygan have a gym?
Absolutely! We offer over 10 house rentals with a gym in Sheboygan. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Sheboygan have a bbq area?
Absolutely! We offer over 60 house rentals with a bbq area in Sheboygan. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Sheboygan have self check-in?
Absolutely! We offer over 10 apartment rentals with self check-in in Sheboygan. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Sheboygan have wifi?
Absolutely! We offer over 130 house rentals with wifi in Sheboygan. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly apartment rentals in Sheboygan?
Sheboygan has more than 30 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Condo Rentals in Sheboygan?
Enhance your stay in our Condo Rentals with the most popular amenities: over 30 homes with wifi, over 10 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

Sheboygan vacation rentals

Top-rated vacation rentals in Sheboygan

Vacation rentals for every style

Apartments

Hotels

Unique stays

Popular amenities for Sheboygan vacation rentals

Stay near Sheboygan's top sights

Other great vacation rentals in Sheboygan

Apartment in Waldo

Apartment in Sheboygan

Guest suite in Sheboygan

Apartment in Sheboygan

Apartment in Sheboygan

Townhouse in Sheboygan

Apartment in Sheboygan

Home in Sheboygan

Other great vacation rentals in Sheboygan

Home in Sheboygan

Apartment in Sheboygan

Apartment in Sheboygan

Home in Sheboygan

Home in Sheboygan

Home in Sheboygan

Apartment in Sheboygan

Apartment in Sheboygan

Quick stats about vacation rentals in Sheboygan

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Where should I stay in Sheboygan?

Are there vacation rentals with a dedicated workspace in Sheboygan?

Are there pet-friendly vacation rentals in Sheboygan?

How much does it cost to stay in house rentals in Sheboygan?

Do house rentals in Sheboygan have a gym?

Do house rentals in Sheboygan have a bbq area?

Do apartment rentals in Sheboygan have self check-in?

Do house rentals in Sheboygan have wifi?

Are there family-friendly apartment rentals in Sheboygan?

What are the most popular amenities for Condo Rentals in Sheboygan?

Destinations to explore