
Pet-friendly holiday rentals in Sheboygan County
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Top-rated pet-friendly home rentals in Sheboygan County
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Pet-friendly house rentals

Sleeps 7{SPACIOUS}Pets Welcome!
they were a great host I felt right at home I give them a 5 star the place was very clean I would recommend them if you are looking for a Airbnb

Norwind Ranch - Peaceful Retreat Near Road America
Flew in for business with Acuity Insurance. Perfect place to stay. Drove up to Green Bay for the Texans vs. Packers game. Only an hour drive from the house in Sheboygan. I will definitely stay here again when I come back to town!

Newly Renovated Beach Front Home in Oostburg WI
Our family stayed with our good friends for a long weekend for a total of 9 including our kids. The house layout worked out well to have our family of four on the upper level and our friend’s family of five on the lower level to give each other some privacy when needed. The sunroom on the upper level is beautiful and it was lovely for watching the sunrise! There was room for everyone at meal time and we felt we had everything we needed to eat in each night. The water pressure in the bathrooms worked well and we managed without a bath tub for the littles. The highlight was the beach where the kids enjoyed hours in the sand. It was very private and quiet, perfect for walks on the beach. Lastly, we picked the location as it was near the Kohler Andre State Park and near Sheboygan where we spent the morning at the water park. Overall an enjoyable trip!

3-bdrm beachfront home on Lake Mich, Sheboygan WI
Now that I have stayed at Jack's home @ 5 times, I can easily verify that every moment spent in that home is magical - steps away from a walk on the beach, the methodical waves lapping on the shoreline, and the majestic sunrises reflecting on the water combine to provide a therapeutic sensory experience that delivers 24 hours each day. If that isn't enough, there are fabulous coffee shops, restaurants, and bars that you can walk to as well as many others a short drive away. No - Jack does not pay me to write these reviews ... the reviews write themselves. Enjoy!

House Near the Lake
This place was great. Block away from the lake. Safe neighborhood. Instructions were clear and place was very clean. If needed plenty of supplies and fresh flowers on the table, nice when we walked into the home. Would book again!

SurfDaze! A Lake Michigan property
This was the perfect getaway to enjoy the gorgeous scenery with the dogs. Cassandra was very responsive and everything was easy from booking to departure. Would definitely go back!

Feel at home in this 3 bedroom, 2 bath home.
Felt like we were staying at a family members home. Very cozy and peaceful setting. We brought our dogs and they loved the large and fenced backyard. Plenty of space in the large bedrooms and living room. Kitchen had everything you could possibly need to cook anything you wanted. Host provided thoughtful treats for the dogs, and beverages and coffee. Even had prepared ice balls for beverages that was a nice touch. We loved our stay, worked great for our needs and would return again in the future if needed.

The Links! - Luxury Golf Retreat
This was an amazing property! Exceptionally clean, updated with great decor. Chris reached out with property details well in advance, and followed up to ensure we had everything we needed. They gave lots of great suggestions of local restaurants and attractions. The garage game room with the simulator was by far our favorite. We got a day in at Road America and two rounds of golf all from the comfort of this place. Highly recommend, we will be back. Thanks Chris!!
Private, pet-friendly home rentals

Charming 2bd/2bath condo
Cheryl was very responsive.

Summit Ranch - Elkhart Lake/Road America- 3 mins
Great location for visiting Road America - just a few short minutes away! We loved watching the sunset and deer from the big front windows. Quick drive to Elkhart Lake for some good restaurants as well.

Cabin moments away from Road America and Lakes
Jeanette’s cabin was perfect for our couples trip to the Road America track. Close to everything and very peaceful at night! Jeanette was very accommodating and we had everything we needed for our stay.

Turn 15 Lodge near Road America
As a crew of 4 + a pup this was the perfect place. We were headed to Road America for the Route 66 Karting Series and could not have picked a more perfect place to stay. So close to track for those early mornings, but also clean, stocked, and comfortable. Not to mention the boys were obsessed with the decorations and RA monopoly game! We will definitely be back next year (if no one snags it first!) Thank you thank you!

Road America Treasure @ Elkhart Lake - 4 bedrooms
excellent host, very warm felt house, a place to relax and disconnect, thank you wendy

North 7th Place - Spacious 2 Bedroom Lower Unit!
We stayed at Chris’s place to visit nearby family with our two children and dog. The apartment was perfect for us: comfy beds and sofas; well-stocked kitchen; loads of games and books for entertainment. Lake Michigan is blocks away, and we took several (longish) walks to the beach and downtown shopping. Chris was quick to return texts, and he was a great host. 10/10 would return!

Casa De Bell - Monthly Rentals Available!
Wonderful place to stay and great communication. Definitely 10 of 10 would stay again .

Cozy Cottage just steps from Lake MI
A terrific location with perfect access to the water. With great decor and thoughtful touches offering lovely hospitality. We'd love to stay again
Pet-friendly home rentals with a hot tub

Stay in the heart of Elkhart Lake at Victorian Inn Resort
Melissa’s place was exactly as described and perfect our weekend getaway. Melissa was extremely responsive and accommodating. We will definitely stay here again! We loved it! Our littles didn’t want to leave either and ask when we can go back to our room in the big white house!

Sleeps 10+, close to Road America, golf and spas!
Great place to stay if you have a lot of people! Plenty of bedrooms and common space. House also has a basement that feels like a completely different place. Great little downtown area close by. Also a great location to stay if you’re going to Road America.

Schoolhouse Straight Inn-Penthouse
We had a wonderful stay at this cozy cabin! The house was clean, well-equipped, and had everything we needed for a relaxing getaway. The surrounding nature was beautiful and peaceful — perfect for morning coffee or evening walks. The hosts were friendly and helpful, always ready to answer any questions. We would definitely love to come back again. Highly recommend!

Resort Condo on Elkhart Lake
Great stay on Elkhart Lake! Located in a central location, you can walk into town for dinner and also great lake amenities right on site. We rented a boat for the day and enjoyed the pool and beach access. We also greatly appreciate Pam being one of the few places we found that is dog friendly!

Resort Life 2 Queen Suite
Great place in the heart of Elkhart Lake. Close to restaurants and an easy drive to Road America.

Private Beach on Lake Michigan: Oostburg Home
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- Erin Hills Golf Course
- Milwaukee Public Museum
- Kohler-Andrae State Park
- Whistling Straits Golf Course
- Bradford Beach
- Harrington Beach State Park
- Milwaukee Country Club
- The Bull at Pinehurst Farms Golf Course
- West Bend Country Club
- Pine Hills Country Club
- Trout Springs Winery
- Heiliger Huegel Ski Club
- Discovery World
- Sunburst
- Blue Mound Golf and Country Club