Dog Boarding Winterset
Find a loving dog sitter to watch your dog overnight at your sitter's home.

Winterset, Find top rated dog boarding
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Azure took care of my older dog (9 year old) and my puppy (7 months old) when our family was out of town for a much needed vacation. She was fantastic to work with! She made sure to do a meet and greet so that my pups could meet her pups to ensure that it would be a good fit for all involved. While I was gone, she sent me picture updates every day (sometimes videos!). I love getting pics while I'm away; it really sets my mind at ease and I appreciate her taking the time to keep in touch with me. When my flight was delayed on the way home, she was flexible and kept my dogs an extra 6 hours or so past when I was originally planning on being home and she was great through all of it. Absolutely would recommend Azure and will be reaching out to her when I need pet sitting services in the future!”
“Kristen took care of our beagle for 5 days/4 nights. She kept us informed by sending pictures daily. She even administered his ear medicine. Chip had so much fun and we were happy to find her!”

“Allison and Nick were so great, you can tell how much they love animals!! We got lots of good updates and they took such good care of our pup. Their big backyard with a tall fence is perfect. I would absolutely recommend them to anyone!”

“Stephanie is wonderful! I had never left my older doggy with a pet sitter before but I felt very comfortable with her in charge. Pips did just fine and I know she was shown love and patience. I would definitely recommend her and hope to book her again!”

“Alex and Jayce were wonderful with our dog. So welcoming and very responsive. Our dog had a great time playing with their dogs. They sent great pictures and we could tell our dog was comfortable at their house. Would recommend to friends and family and will use them again!”

“Our boys had a blast with Jennofer and her family! They even seemed a bit disappointed to go home with us! We got wonderful daily (sometimes twice daily) updates with the best photos. Will definitely recommend and use her again!”

“They took such great care of our dog (Bear)! They took him for walks and took lots of pictures of him having fun with the other dogs and feeling right at home! I knew he was in good hands, and they will be keeping him again!”

“Cory was very kind and made me feel so comfortable with leaving my pupper (Roko) with him. The communication was 100%, great amount of space for Roko to run off his energy and play, and just awesome understanding and care for him. I will be rebooking for the next time we have a family trip because my Roko felt so loved and comfortable and happy here.”

“Cassandra did a great job taking care of Banjo for two nights. Communication was excellent (photos and videos, along with messages about how he was doing), and Cassandra was willing to accommodate drop-off and pickup requests to fit my schedule for the weekend. I have always been apprehensive about boarding my dogs at a kennel if I have to go out of town for more than one night. Cassandra made Banjo feel at home and kept him in a normal, relaxed environment and routine.”

“We would definitely use Agnatha again. Our girl doesn't like when we leave her with other people but she did really good with Agnatha! Agnatha was very responsive when I messaged her, she set up a meet and greet well in advance of our trip, and sent photos and updates everyday we were gone!”

“Geleea was amazing with my cat and helped her feel right at home. She provided me with pictures and videos ensuring her safety and also took her in pretty last minute! thank you so so much!”

“Highly recommend Karisa! She kept me updated throughout their stay and sent me pictures. She also sent them home with homemade dog cookies. Her house looked very clean and my dogs were happy and healthy when they returned home.”

“April and the kids did great with Gus. We like her location to be able to walk him in the Pufferbelly. Gus stayed for the weekend and came back tired. She provided pictures and assurance. We will use her again.”

“Emily was amazing with watching Whiskey. She updated me with pictures throughout the entire stay and was quick to respond. Her fur babies and Whiskey all got along wonderfully as well and loved all running and playing in her fenced in backyard.I highly recommend Emily and her household for hosting a stay for your loved one. Will definitely be going through Emily for any future visits to Fort Wayne in the future.”

“Omg Anne was simply amazing and super easy to work with. She was able to accommodate me while my plans changed and allowed me to be able to put my mind at ease knowing my fur baby was being well taken care of. I will be using her on an ongoing basis and I strongly recommend her to care for your pets any day of the week. I appreciate this app so much!!”

“Hannah and Haley did a great job with my baby! A perfect fit for Jamie's separation anxiety, since he was never home alone, and he came home a very tired baby after playing with Hannah's dogs all weekend. He didn't seem to want to leave!”

“Heather was a wonderful sitter for my 11 month old puppy. She was very flexible with drop off and pick up. She was communicative and sent me photos and updates. I would definitely use her again.”

“Millie and her family took great care of our dog Buster! She is super attentive and communicates really well. She sent us updates twice a day with pictures. She was very flexible with our schedule which was so much appreciated because we were coming in from out of town. We could tell when we picked Buster up that he was very well cared for! Overall so so great!! Definitely recommend 100%!”

“Natalie is wonderful! Cola had the best time playing catch with her dogs and cooling off in the pool. Natalie sent updates throughout the weekend as well!”

The median cost per night for dog boarding in Winterset is $37
Dog parents share their Rover experiences - Winterset
Joscelyn and her family took such good care of Willow! My husband and I had no worries whatsoever about her staying with them and felt we could fully relax while we were away. I honestly think our dog had more fun with them playing with their dog than at our house 😂. We WILL be taking Willow over again when we have to be out of town.

Cassandra did a great job taking care of Banjo for two nights. Communication was excellent (photos and videos, along with messages about how he was doing), and Cassandra was willing to accommodate drop-off and pickup requests to fit my schedule for the weekend. I have always been apprehensive about boarding my dogs at a kennel if I have to go out of town for more than one night. Cassandra made Banjo feel at home and kept him in a normal, relaxed environment and routine.

I had a great experience with this dog sitter. He was very kind and accommodating, especially since my booking was very last minute. He still made the time to come get and take care of my dog, which I really appreciated. He also sent me pictures while she was with him, which reassured me that she was safe and doing well. This was my first time being away from my dog, so I was a little nervous, but he made the experience much easier and more comfortable for me. It was such a relief to know she was safe and even having fun. Overall, the service was excellent and I would definitely recommend him to anyone looking for someone trustworthy and caring to watch their pet.

She was great with my dog, super communicative, sent pics/vids, and was flexible when my plans changed. Being new to town, I was nervous leaving my dog with a stranger, but she made the whole thing smooth and my dog seemed to enjoy his time with her. Definitely would recommend!

Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?
Cashless payments
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Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local sitters who will treat your dogs like family

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