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Luxury Downtown Sheboygan 4BR - 3 Bath - 3 min walk to beach - Lakeside Legacy

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Golf
Dining
Interior
Interior
Golf

Reviews

9.8 out of 10
Exceptional

Entire home

4 bedrooms3 bathroomsSleeps 9

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

Explore the area

View map
Sheboygan, WI
  • Place, John Michael Kohler Arts Center
    ‪8 min walk‬
  • Place, Stefanie H. Weill Center for the Performing Arts
    ‪8 min walk‬
  • Place, Blue Harbor Resort & Conference Center Water Park
    ‪18 min walk‬

Room options

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Exterior

Inn On Woodlake

Kohler
  • Breakfast included
  • Pet-friendly
  • Free Wi-Fi
  • Restaurant
4.7 out of 5, Exceptional, 264 reviews
The price is AU$316
includes taxes & fees
6 Apr - 7 Apr
Inn On Woodlake

About the area

Sheboygan

This holiday home places you in the centre of Sheboygan, within a short 5-minute stroll of Lake Michigan and North Side Municipal Beach. Highlights at this beachfront holiday home include a kitchen, a washing machine and free WiFi. .Home features 3 bathrooms, a fireplace and a patio. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. In-room jetted baths, a living room and a dining area are also available. Housekeeping is available on request. .Spend the day at the beach where you'll find sunloungers. Other amenities include laundry facilities, a garden and barbecues. .Sights within a 15-minute walk of this Sheboygan holiday home include Deland Park and Above & Beyond Children's Museum.
View more Holiday homes in SheboyganOpens in a new window

What's nearby

  • North Side Municipal Beach - 2 min walk - 0.2 km
  • John Michael Kohler Arts Center - 8 min walk - 0.7 km
  • Stefanie H. Weill Center for the Performing Arts - 8 min walk - 0.7 km
  • Above & Beyond Children's Museum - 10 min walk - 0.9 km
  • Blue Harbor Resort & Conference Center Water Park - 18 min walk - 1.5 km

Restaurants

  • ‪Sheboygan YMCA - ‬7 min walk
  • ‪Uptown Slice - ‬14 min walk
  • ‪Umi Sushi - ‬16 min walk
  • ‪Tochi Ramen - ‬14 min walk
  • ‪Harbor Lights - ‬11 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Luxury Downtown Sheboygan 4BR - 3 Bath - 3 min walk to beach - Lakeside Legacy

Grand colonial meets coastal luxe in this 2800 square ft, 4 bedroom home along the magnificent Lake Michigan coast. Stunning views throughout. Perfect for group golf getaway or family vacations! Kid-friendly. Steps from the beach. Blocks from downtown restaurants and bars. 8 min drive to Kohler golfing. Designer linens, furnishings and finishes. 2 media rooms. Sunroom. Chef's kitchen with all your cooking/serving needs. Spa master bath. Pergola and BBQ grill. No pets. Location is quite and peaceful.

3 King beds, 1 Queen bed with XL twin trundle - sleeps a total of 9.

Bedroom 1 - King Bed - Main Floor
Master Bedroom - King Bed - Second Floor
Bedroom 3 - King Bed - Second Floor
Bedroom 4 - Queen Bed with Twin XL trundle - Second Floor
Pack and Play available upon request.

Top of the line mattresses and organic linens ensure you’ll have the best nights sleep. TV's and ceiling fans in all bedrooms.

We use hospital grade cleaning supplies.

Master suite features a Kohler therapeutic infinity edge soaking tub and oversized spa shower. Two more full baths newly renovated.

Chef’s kitchen with top of the line appliances, quartz countertops, and everything you need to serve up a delicious meal or prep a picnic. Griddle, waffle maker, air fryer, and Keurig coffee maker (in addition to regular coffee maker) provided. Open concept dining room with a table for 8/10 anchored by a gas fireplace.

Large walk in pantry off kitchen with washer/dryer, recently renovated. Loads of shelving to bring in your favorite foods and supplies.

Two media rooms, including a massive light drenched sunroom and designer furnishings and finishings throughout. Children's toys, books and games provided. Hi-Chair and Pack N Play provided.

Desk and office chair located in Master BR and another Desk and office chair located in LL family room for office needs.

Fenced front and back yard including new louvered pergola, seating for 12, string lights, Bbq grill. The back yard is private and quiet.

Attached 2 car garage, additional 2 car driveway, and easy off street parking.

Stairs at the end of the cul-de-sac lead down to the beach. Quiet community park just around the corner. Less than a 5 minute walk to downtown Sheboygan’s finest restaurants, bars, shopping, JM Kohler Art Center, and Children’s Museum. 10 minute drive to Kohler golf courses.

Beach towels, beach tent, chairs, toys, and coolers are provided to take to the beach.

4 Bicycles are available for you use to explore historic Sheboygan, located conveniently in the garage. If more are needed, there are several bike rental shops nearby.

-Kid-friendly.

-No pets allowed.

-No smoking of any kind or vaping allowed inside or out. Guests must fully exit property grounds to do so.

-No events or parties. No more than 4 guests that are not listed in booking allowed on property at any time without prior approval of ownership.

-The primary renter must be at least 25 years old to book this property and present for the entire stay.

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Watershed Hotel
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  • Breakfast included
  • Pet-friendly
  • Parking included
  • Free Wi-Fi
4.8 out of 5, Exceptional, 513 reviews
The price is AU$178
includes taxes & fees
6 Apr - 7 Apr
Watershed Hotel

Property amenities

Beach

  • On the beach
  • Beach loungers
  • Beach towels

Ski

  • Cross-country skiing nearby
  • Snowboarding nearby

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Onsite parking options include a garage

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 3 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Jetted bathtub
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room
  • Separate dining area

Entertainment

  • Books
  • Games
  • Smart TV

Outdoor areas

  • Barbecue grill
  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • No lift
  • Step to reach entrance
  • Well-lit path to entrance
  • Smoke-free property

Services and conveniences

  • Housekeeping on request
  • Iron/ironing board

Location highlights

  • In the city centre
  • Near a hospital
  • Near the marina
  • Next to a golf course
  • On a lake
  • On the waterfront

Things to do

  • Bicycles
  • Basketball nearby
  • Birdwatching nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Hunting nearby
  • Ice skating nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Mountain biking nearby
  • Sailing nearby
  • Sledding nearby
  • Snowmobiling nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Bicycles
  • Garden
  • Housekeeping (on request)
  • Recycling

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you to complete the following before checking out:
Load and start the dishwasher
Gather used towels
Remove personal items and take out the rubbish
Turn off the lights and lock the doors
Failure to complete these may result in a negative review from the host.

Rules

This property is exclusively for the use of the registered guests. Subletting or unauthorized occupancy is not permitted.

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit and a deadbolt lock in all accommodation.

Frequently asked questions

Are there any beaches close to Luxury Downtown Sheboygan 4BR - 3 Bath - 3 min walk to beach - Lakeside Legacy?

Yep, Luxury Downtown Sheboygan 4BR - 3 Bath - 3 min walk to beach - Lakeside Legacy is a short 3-minute walk from North Side Municipal Beach. Fun beach activities include jet skiing, water tubing and waterskiing. You can also find motor boats.

Does Luxury Downtown Sheboygan 4BR - 3 Bath - 3 min walk to beach - Lakeside Legacy have a pool?

No, this holiday home doesn't have a pool.

Is Luxury Downtown Sheboygan 4BR - 3 Bath - 3 min walk to beach - Lakeside Legacy family-friendly?

You bet! With amenities such as a playground and laundry facilities, as well as children's dinnerware and children's books, it's no surprise that Luxury Downtown Sheboygan 4BR - 3 Bath - 3 min walk to beach - Lakeside Legacy is a winner with our family travellers.

Is there a private hot tub at Luxury Downtown Sheboygan 4BR - 3 Bath - 3 min walk to beach - Lakeside Legacy?

No, but there is Jetted Baths.

Is there a free airport shuttle available at Luxury Downtown Sheboygan 4BR - 3 Bath - 3 min walk to beach - Lakeside Legacy?

No, Luxury Downtown Sheboygan 4BR - 3 Bath - 3 min walk to beach - Lakeside Legacy does not offer an airport shuttle service.

What time are check-in & check-out at Luxury Downtown Sheboygan 4BR - 3 Bath - 3 min walk to beach - Lakeside Legacy?

Check-in begins at 4:00 PM. Check-out time is 10:00 AM.

Are pets allowed at Luxury Downtown Sheboygan 4BR - 3 Bath - 3 min walk to beach - Lakeside Legacy?

No, pets are not allowed.

Is there a golf course on site at Luxury Downtown Sheboygan 4BR - 3 Bath - 3 min walk to beach - Lakeside Legacy?

There is a golf course next to Luxury Downtown Sheboygan 4BR - 3 Bath - 3 min walk to beach - Lakeside Legacy.

Luxury Downtown Sheboygan 4BR - 3 Bath - 3 min walk to beach - Lakeside Legacy Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 34 out of 37 reviews
Rating 8 - Good. 2 out of 37 reviews
Rating 6 - Okay. 0 out of 37 reviews
Rating 4 - Poor. 1 out of 37 reviews
Rating 2 - Terrible. 0 out of 37 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Laura R.

Liked: Cleanliness
Very easy check in to this comfortable and spacious home. It had every amenity we needed and served our family well.
Stayed 3 nights in Aug 2025

10/10 Excellent

Janet K., WI

Liked: Cleanliness
Beautiful & spacious home in a nice neighborhood. Met all of our needs.
Stayed 4 nights in Jul 2025

10/10 Excellent

Jane B.

Liked: Cleanliness

Probably the best VRBO we’ve ever stayed at !

Got out to such a great start with the owner - Linda last winter. She was so helpful giving me info about the area and she even helped me find the perfect place to host my son’s rehearsal dinner. It got better and better - her house is beautiful- very well decorated and stocked . Appliances are top quality -nice dishes and cookware. She has thought of everything- nice coolers - nice bikes , extra blankets , lots of beach towels . Use of a big , pristine garage is nice too. Darling enclosed backyard area with pergola and party lights. Grill in garage available too. Kids toys and books were available. So many nice touches made our stay so great. House is very close to the beach . It’s almost like Linda thought of everything we needed . It was the perfect place to stay while celebrating our family’s wedding.
Stayed 7 nights in May 2025

10/10 Excellent

David W.

Liked: Cleanliness

Great stay. Recommended.

We really enjoyed the Lakeside Legacy house. Very comfortable, well appointed, thoughtfully designed, and close to the lake / downtown. Linda was a great host. No complaints.
Stayed 3 nights in Nov 2024

10/10 Excellent

Douglas L.

Liked: Cleanliness

Weekend Away

Loved everything at this property. Had a fantastic stay. Easy walk to beach but yet felt very private.
Stayed 2 nights in Aug 2024

10/10 Excellent

Gerry H.

Liked: Cleanliness

Golf trip to whistling straits

Couldn’t have been better
Stayed 2 nights in Jul 2024

10/10 Excellent

Eileen S.

Liked: Cleanliness

Lakeside Legacy luxury!

We had the best week at the Lakeside Legacy home. Everything was just as we hoped for- home was spacious, beautifully decorated, super well-stocked and conveniently located close to the beach, golf, etc. Linda was the perfect host, providing every last detail and being on hand for any questions. We also appreciated having a grill, comfortable outdoor seating area and bikes to ride! We loved our stay here and would highly recommend it!
Stayed 6 nights in Jul 2024

10/10 Excellent

Verified traveller

Liked: Cleanliness

Lovely Saugatuck- Who Knew!

Beautiful and well appointed home was the perfect setting for our family reunion/daughter wedding. The super open kitchen dining room area accommodated our group perfectly. We were one block from the beach and access was easy. Outdoor seating area felt warm and private. Bedrooms were clean and comfortable. Would book this home again in a heartbeat.
Stayed 3 nights in May 2024

10/10 Excellent

Brenda H.

Liked: Cleanliness

Teacher Getaway

Spectacular and so easy! Our host was in constant communication with us. She gave restaurant suggestions, brought out the patio furniture cause she had checked the weather and thought we might use it, and made the whole process simple. I couldn’t have asked for a better property to stay on. Location was exactly what we wanted as we could walk to downtown but also to Lake Michigan. I will definitely be returning! Thank you!
Stayed 2 nights in May 2024

10/10 Excellent

michelle r.

Liked: Cleanliness

Thanksgiving with family and friends

Holidays are rough since our Mom passed. We decided to try something new in a different location. This home was absolutely beautiful and CLEAN! The host was wonderful too! I’m super happy we were able to create new memories at Lakeside Legacy. We plan to come back again in the future. Thank you again to the wonderful host. You made this new memory one I will most definitely treasure.
Stayed 3 nights in Nov 2023

10/10 Excellent

Noelle M.

Liked: Cleanliness

Comfy, Cozy, Immaculate, Relaxing, Spacious, Great Location & Responsive Host

Thank you for sharing your beautiful home. We enjoyed it very much. Hope to be back one day.
Stayed 1 night in Oct 2023

8/10 Good

Kris B.

Liked: Cleanliness

October weekend

the location of this property in a historic district is amazing; you can choose to walk by the lake or take a walk by many historic homes in Sheboygan. House was clean, many areas to relax and enjoy.
Stayed 2 nights in Oct 2023

10/10 Excellent

Carolyn W., St. Louis, Missouri

Liked: Cleanliness

We ❤️ Sheboygan

Your home was just perfect for our family. We seem to be staying a little longer each time we visit Sheboygan. The windowed living room was our favorite room to hang out in. The bedding was also VERY comfortable and we all had good sleeps! Thanks for having everything we needed for the perfect trip.
Stayed 4 nights in Aug 2023

10/10 Excellent

Amy K.

Liked: Cleanliness

Great place

We were very pleased with everything and would rent again if in the area.
Stayed 2 nights in Jul 2023

10/10 Excellent

richard l.

Liked: Cleanliness

Sheboygan House

great house in a peaceful neighborhood close to the lake. Just what we needed.
Stayed 5 nights in Jul 2023

10/10 Excellent

Don B.

Liked: Cleanliness

Great time on a Great Lake

The property is as advertised, first class, great location, and really nice for a larger family. Communication with the property owners was always quick and easy. The only concern was a security camera on the patio...
Stayed 5 nights in Jul 2023

8/10 Good

John T., Fort Myers, Fl

Wonderful property

Very helpful owner in a perfect middle America town.
Stayed 3 nights in Sep 2022

10/10 Excellent

Drew M.

Liked: Cleanliness

Great place!

Great location and home!
Stayed 3 nights in Sep 2022

10/10 Excellent

Sharon H.

Liked: Cleanliness

Great location on the Lake

My family enjoyed their stay at this beautiful home. My grandson languished in the huge bathtub and we were able to share family stories in the beautiful sunroom. Many thanks for the opportunity to enjoy Sheboygan for one last time.
Stayed 2 nights in Aug 2022

10/10 Excellent

Eric S.

Liked: Cleanliness

Great property

Overall great experience!
Stayed 3 nights in Jul 2022

10/10 Excellent

Corey R.

Liked: Cleanliness

Yearly lake vacation

My girls and I loved the house. Very well equipped and all the amenities were excellent. Would come back again without a hesitation.
Stayed 4 nights in Jul 2022

10/10 Excellent

Sarah S.

Liked: Cleanliness

Wonderful Stay in Sheboygan!

My husband and I traveled to Sheboygan for a conference with our 4 month old and my parents. We had more than enough room and were pleasantly surprised that it was even better than the pictures! We walked to the lake everyday and could even hear it from the master window. I highly recommend and definitely would stay here again!
Stayed 3 nights in May 2022

10/10 Excellent

Kim Y.

Liked: Cleanliness

Family Trip

My husband and I brought my 90 year old Mother and my sister for a little family reunion to visit relatives. The house was soooo comfortable for my Mom. This was her first VRBO experience and having meals and relaxing in this wonderful home made it extra special for her😍
Stayed 4 nights in May 2022

10/10 Excellent

Nancy F., Houston, TX USA

Liked: Cleanliness

Wish I were still there...

We have stayed in places around the globe and I always know the best ones when we are sad to leave! This is one of those places! The location is outstanding. It is a quick walk to the beach and the water can be seen from the house. I was able to crack the window in the master and fall asleep to the sound of the waves. Heaven! It is close to great restaurants, as well. We were there over the Christmas holiday to visit family and I was able to easily cook in the amazing gourmet chef's kitchen, which is well stocked and organized. But my favorite room had to be the large sunroom with the comfy L-shaped sofa. I got up early just to have coffee by myself in this cozy, peaceful spot. So nice to relax with family in this beautiful home. Michelle was also very helpful and sweet with excellent communication. Can't wait to go back! Thank you, Michelle!
Stayed 5 nights in Dec 2021

10/10 Excellent

Sean E., Overland Park KS

Liked: Cleanliness

Great house!!

What a wonderful home. I would highly recommend staying here whether not it’s the winter or the summer. Very clean and a very comfortable place to stay. Thank you
Stayed 2 nights in Dec 2021