Pet-friendly holiday rentals in Oshkosh

I had a last minute trip on a Friday night and needed to book a place to stay while driving. Brandon was response and able to accommodate us with only about 4-5 hours heads up. We didn’t get in until late and had trouble with the keypad but as soon as I messaged I still got a quick response and was easily able to get in through the garage. So appreciated!!

I was in town for my dad’s memorial and Shawn worked with me to ensure that I was able to focus on my family during that time. We needed a peaceful location where I could bring my mom and her houseguests for meals and relaxation while we prepared her house for the gathering. Shawn’s house was perfect with plenty of indoor and outdoor seating, including a lovely fire pit with wood for evening fires. The deck was a lovely place for morning coffee. A bonus for the kids were all the “hidey holes” throughout the that made the house seem almost magical. Watching the lift bridge go up and down, the bank anglers, princess parties at the lovely park across the canal all added to the charm while still feeling very private. Highly recommend!

Nathan and Sarah’s home is the perfect getaway for anyone traveling with kids or dogs. Thoughtfully equipped with everything you could need—from a fenced-in backyard and comfy beds to a washer/dryer and even a Pack ’n Play—they’ve truly thought of it all. On top of that, they’re incredibly responsive and welcoming hosts. Honestly, this place is a must-stay!

Everything was great.

Communication was super helpful and fast. At the last minute we were able to bring a pet (and pay the fee) but I was thankful for how easy it was. The house worked great for my family and adult kids and mother as we all drove to Appleton for a family wedding. The beds were SUPER comfortable and i LOVED that it has a Keureg.

Super cool property and cute little home. Quiet and cozy for our fam of three including infant, as well as our dog. Loved visiting the Oshkosh farmer’s market and enjoying the sunrises and sunsets at the house. We hope to return sometime, thanks!

Great stay! Beautiful location with great view and access to lake. Home was clean and just as described. Host was responsive and made for a seamless stay. Will be back. Highly recommend.

Great cozy space with everything we needed. Angie was a great, flexible host who got back to us quickly with any questions. Great location for what we needed. We would stay there again!

House was amazing! Host was great! Will be back soon! everything is accurate as shown and in top condition looking forward to come back when the weather is nicer!

Great stay! My group loved it and had a blast. House was Beautiful & Host was GREAT, was very understanding and helpful. DEFINITELY recommend and would love another stay sometime.

Beautiful home felt like home!! Very roomy and cozy. Thanks Thomas for being responsive and answering my questions. Me and my family had a great time!!! Will definitely book again at this location or other locations you have.

Our stay at the Old Schoolhouse was great! The house was clean and well organized and had all the things we needed. The grounds were beautiful and we had a great time swimming in the pool, relaxing in the hot tub, and gathering at nights around the fire pit. Communication from Heather was fast and she thoroughly answered my questions. We had a great time at the Old Schoolhouse and would absolutely stay there again! Thank you, Heather!

Loved everything about the home. Loved collecting eggs from the chickens. Hot tub, fire pit , yard, and inside areas were perfect and comfy. Loved the lay out of the house and the view from the sun room was great. Responsive hosts and great directions in the house manual left in the kitchen.

Beautiful house! Very comfortable and has everything you need and more.

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!

Welcoming and attentive caretaker, kitchen amenities, fun for multi-generational groups, hot tub is divine, fun touches. For once, the teen and college-aged boys weren’t bored. I bet it’s even better in the summer. The upstairs bathroom would be happier with one more light. 💡:)

Lovely place, stayed there for half a year. Location is near pretty much any store you can think of. Garage is tight if you have a large vehicle. Neighborhood is very nice and backyard has a nice creek!

Rachael Cottage was everything we wanted and more. Cozy, comfortable, and had some of the most beautiful views of the Wolf River. Very safe and friendly neighborhood.

The Cabin in Ripon was a beautiful, rustic log cabin. Very nicely furnished and decorated. Lots of essentials available. Kitchen was well stocked. Plenty of seating space in the living room. Very helpful instructions on lights and how to find things in the house. Plenty of outdoor space and privacy and wood provided for campfire. Hosts were very responsive and asked ahead of our stay if we needed a pack and play or bassinet for our infant. Lots of kids books and board games available to use. We had a very nice stay and would highly recommend!

Great weekend family stay at Sandra’s place. Kids did not want to leave. We used the kayaks on both sides of the house. Saw lots of birds, fish (the carp were laying eggs, caught catfish in the river), turtles and a little otter. The boardgames and super Mario were fun at the end of the day. Sandra made us comfortable. Little extras around to make us at home. Easy checkout process.

Rachel’s place was beautiful, felt like home. It was peaceful to sit and watch the birds and see the trees come to life in spring. Easy location to get round and George’s steak house was Diane worth going to. Get place for families or for anyone.

We had a great stay at this cozy house on Lake Winnebago with a nautical theme. You’ll have everything you need with a large TV, comfortable furniture, washer and dryer, and the best selection of Kreurig coffees. Danielle is very helpful and quick to answer any questions.

This is our 4th time visiting this cabin and it never disappoints! The last time my now husband and I were here was a few years ago when we got engaged at the park down the road. We love sitting by the fire, fishing by the pier and cooking yummy meals. We always leave feeling relaxed and rejuvenated.

The cabin was exactly the kind of peaceful break we were looking for. We try to include our dogs on road trips (especially as they’re getting older😭), so we were grateful to find a dog-friendly spot! We really appreciated how clean the cabin was, from the crisp bed linens to the bleach bucket for sanitizing dishes before use. We spent our time soaking in the sounds of nature, reading, relaxing by the bonfire, and watching movies. The dogs found their zen sunbathing on the deck. It was a much-needed change of pace from everyday stress. Highly recommend. Thanks, Hannah and Caleb!