Pet-friendly holiday rentals in Sheboygan County

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Sheboygan County pet-friendly home rentals

Pet-friendly house rentals

Guest favourite
Home in Sheboygan
4.97 out of 5 average rating, 37 reviews

Sleeps 7{SPACIOUS}Pets Welcome!

DanielRating, 5 stars3 months ago
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!
Top Guest favourite
Home in Sheboygan
5 out of 5 average rating, 20 reviews

Norwind Ranch - Peaceful Retreat Near Road America

MichaelRating, 5 stars6 months ago
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!
Superhost
Home in Plymouth
4.72 out of 5 average rating, 18 reviews

Summit Ranch - Elkhart Lake/Road America- 3 mins

TamaraRating, 5 stars8 months ago
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.
Guest favourite
Home in Sheboygan
4.94 out of 5 average rating, 51 reviews

3-bdrm beachfront home on Lake Mich, Sheboygan WI

JohnRating, 5 stars6 months ago
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!
Top Guest favourite
Home in Sheboygan
4.96 out of 5 average rating, 76 reviews

House Near the Lake

AshleyRating, 5 stars1 day ago
Quiet location in a beautiful, safe neighborhood. Great amenities in the home as well - puzzles with a puzzle board, a large new TV, extra seating in the living room. My husband and I enjoyed our stay very much and appreciate the hosts’ communication around anything and everything we needed during our stay.
Superhost
Home in Plymouth
4.81 out of 5 average rating, 37 reviews

Lake Front Cottage With Dock. Walk to Road America

JamesRating, 5 stars7 months ago
Nice place and nice people, would go back for any events I find myself at Road America.
Top Guest favourite
Home in Sheboygan
5 out of 5 average rating, 20 reviews

Feel at home in this 3 bedroom, 2 bath home.

DylinRating, 5 stars8 months ago
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.
Top Guest favourite
Home in Sheboygan
4.99 out of 5 average rating, 67 reviews

The Suncatcher -Steps from Lake - Fenced Yard

ValerieRating, 5 stars2 days ago
Our stay at Jessica's place was wonderful! The house was super clean, quiet, beautiful, comfortable and cozy, and had a great backyard. The neighborhood was quiet and close to the gorgeous lakeshore. She was also super responsive and kind and helpful! We loved everything about our stay - amazing place and host!!

Pet-friendly home rentals with a pool

Private, pet-friendly home rentals

Top Guest favourite
Home in Elkhart Lake
4.93 out of 5 average rating, 31 reviews

Aspen House - peaceful & private country home

SherryRating, 5 stars7 months ago
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!
Superhost
Cabin in Plymouth
4.71 out of 5 average rating, 75 reviews

Cabin moments away from Road America and Lakes

DarinRating, 5 stars7 months ago
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.
Top Guest favourite
Home in Plymouth
4.91 out of 5 average rating, 11 reviews

Turn 15 Lodge near Road America

SamanthaRating, 5 stars1 week ago
This was our first time racing at Road America and Dean and Lori's place was absolutely perfect. It is so close, you can actually walk over to the track in the nice weather, and there are plenty of other great areas to explore on foot as well! Their home is perfectly comfortable and enjoyable while being subtly themed with fun racing references. We will definitely be back to Road America, and plan to stay at this home every time possible. Thank you so much for making our first weekend here an enjoyable one!
Home in Plymouth
4.9 out of 5 average rating, 10 reviews

Pleasantview Valley Country Family Home

DaelenRating, 5 stars9 months ago
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.
Top Guest favourite
Condo in Sheboygan
4.93 out of 5 average rating, 40 reviews

Ellis District Urban Lake Condo

ChristyRating, 5 stars3 weeks ago
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!
Guest favourite
Apartment in Sheboygan
4.96 out of 5 average rating, 56 reviews

North 7th Place - Spacious 2 Bedroom Lower Unit!

Shelley MRating, 5 stars1 month ago
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!
Guest favourite
Home in Sheboygan
4.89 out of 5 average rating, 18 reviews

Dog-Friendly Sheboygan Home - 1 Mi to Town!

TimRating, 5 stars1 week ago
Remarkably clean house. Easy and flexible checkin process. Had so much fun at the Airbnb owner’s bar/restaurant (Scenic Bar). Would definitely recommend this place to anyone looking to visit the area!
Guest favourite
Home in Sheboygan
4.91 out of 5 average rating, 35 reviews

Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan

JillRating, 5 stars8 months ago
Very nice place to stay, great location too. They were prompt with communication.

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