
Pet-friendly vacation rentals in Sheboygan County
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Top-rated pet-friendly home rentals in Sheboygan County
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Popular amenities for Sheboygan County pet-friendly home rentals
Pet-friendly house rentals

Sleeps 7{SPACIOUS}Pets Welcome!
There were no mice or roaches. There was not any kind of sticky goo on the floor or in the sinks. Everything was clean! The dishes were especially spotless. The refrigerator cold our food perfectly. The televisions in each room had crystal clear high definition and excellent sound quality. We baked cookies in the oven and they turned out great. I overcooked a pizza and the smoke detector was fully functional and might have saved our lives. We felt secure and safe with a numeric door lock where only we knew the secret code. The beds were soft and comfortable. I would highly recommend this property to anyone. If you like living the dream this is the place for you!

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!

Summit Ranch - Elkhart Lake/Road America- 3 mins
This place was perfect. If you're headed to Road America, the location could not be better. The home is right in between the race track and Elkhart Lake. We watched deer from the front window. This home was very comfortable and clean, I would definitely stay here again.

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
Walking in felt like walking into my grandmother's mid century home. It was clean and well stocked. The hosts were very responsive and easy to work with. Tamara even had dishes set out for our dogs. We felt very comfortable and right at home. There is a beach run for the dogs within a short walking distance. We spent a lot of time there! We will return on our next visit to Sheboygan.

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 Suncatcher -Steps from Lake - Fenced Yard
I am quite picky when it comes to my stats at Airbnb. Jessica's place stands out. I'm not a fan of clutter and Sun Catcher was just perfect. Such a cozy bed and the layout is great. Would highly recommend.

Beautiful Home Near Lake Michigan & Downtown
We have stayed at Jocelyn's now 4 times so we knew we were getting a great "home" away from home. I highly recommend a stay at Jocelyn's you will not be disappointed.
Pet-friendly home rentals with a pool

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!

First Floor Queen with Single Pull-out
A very nice experience overall. Very responsive with questions and the location is very convenient for swimming, ice cream, getting on the lake, etc.

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!
Private, pet-friendly home rentals

Aspen House - peaceful & private country home
This was a perfect place to relax after a day at the race track. The home is spacious and had everything we needed for our stay. Would come back again!

Cabin moments away from Road America and Lakes
I really enjoyed staying in the cabin. It is just minutes from Road America which made it great. There was room for me to park my truck and trailer when arriving late. Jeanette was available when I arrived to help assist which was very nice. I would highly suggest having a meal or two next door at Rumors Roadhouse. I ate there 3 nights having something different each night and the food was excellent. Jeanette was very responsive if I had any questions or needed anything. I look forward to staying there again next year.

Turn 15 Lodge near Road America
When visiting Road America, this Airbnb is an absolute must-stay. It’s the most well-stocked and thoughtfully equipped place I’ve ever experienced. Dean and Lori are exceptional hosts, with outstanding communication and an eye for detail that makes all the difference. They’ve truly thought of everything a traveler might need. I’ll definitely be returning in the future!

Pleasantview Valley Country Family Home
Overall great place to stay for our needs. Easy to get to, close to Road America (12 min drive), host was very communicative, and helpful.

Secluded Country Farm Getaway
Sarah has a great place in the country that allows you to get close to nature, while also staying comfortable in the camper with lots of amenities. Our daughter absolutely loved interacting with the chickens, goat and especially the cow. The hiking trails are great. Sarah is a welcoming host and went out of her way to make sure we had everything we needed for a fantastic visit!

Ellis District Urban Lake Condo
Sara was very responsive accommodating for our needs. The space itself was spacious for the size, the kitchen was well equipped with any cooking you may do, tons of towels and travel size toiletries in vase you forgot something walking distance to the marina was a nice option, however it was a tad nippy so I chose to stay inside while my husband and son were in the airspft event. will definitely stay again!

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!

Dog-Friendly Sheboygan Home - 1 Mi to Town!
Had a great time with my wife, very peaceful and relaxing. Except her, but I don’t mind it. We will be back again.
Destinations to explore
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- Milwaukee Public Museum
- Erin Hills Golf Course
- Kohler-Andrae State Park
- Whistling Straits Golf Course
- Milwaukee Country Club
- The Bull at Pinehurst Farms Golf Course
- Harrington Beach State Park
- Heiliger Huegel Ski Club
- Trout Springs Winery
- Bradford Beach
- West Bend Country Club
- Sunburst
- Blue Mound Golf and Country Club
- Discovery World
- Pine Hills Country Club