Dog Boarding in Winterset, IA
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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Top rated Winterset dog boarders
“Milli had a great weekend with Erin & Chris! They spoiled her while she was there! She also was very relaxed even after she returned home! I would definitely recommend them and appreciate that they limit the number of dogs at one time! Thanks Erin & Chris!”
“Jessica was great with our dog Louie, loved the pics and vids during his stay. Booking and communication was easy and efficient. Highly Recommended, and many Thanks!”
“Samantha was amazing!! I’m always hesitant to leave my fur baby with just anyone but Samantha gave us piece of mind and we were confident that he was well cared for! He had a ball and we have a new puppy sitter!!!”
“We needed a sitter at the last minute and Clare was able to take our little dog. I feel she took wonderful care of Chewey with ample walks and plenty of attention and sent pictures of a happy dog relaxing in the sun.”
“Alice was an amazing sitter!! She sent me daily updates and my pup loved to play with hers. She was in constant communication and always answered. Thank you for watching my sweet boy!”
“I boarded my little pomeranian with Deborah for a long weekend. She was great! She sent me a picture and messages every day of what Harley was doing. She is so friendly and we hit it off right away. I will definitely use her again for Harley.”
“They took extra special care of Pause and made sure he felt at home. They even sent him home with an extra doggie bag of treats!! He is tired out from all the fun and will be staying over again in the future!”
“Lifesaver and LOVES animals. Never left my dog with anyone other than my mom and I didn’t feel nervous at all. Sent me pictures and played with blaze. BLAZE LOVED THE BIRDS 🤣🫶🏼”
About: I have spent my entire life around animals, especially larger, older dogs. I am home full time while classes are online and am very flexible with sitting times. I am currently taking classes online for the summer, so I have plenty of time to take care of your furry friends! I tend to be busier on the weekends but if you give enough time in advance I am pretty flexible. I live in an apartment complex, and don't have a yard, so animals will have to be leashed when outside. I do not have a lot of space, so smaller animals are preferred, especially for longer stays.
“Sherilynn was great! First time using rover and someone non-family watching our dog. With her providing daily updates we were quickly comforted. We will use her again!”
“This was the second time Lara and Cary watched our pup. They were great as always and would absolutely recommend! They were flexible and very accommodating to our dog’s needs.”
“We are so thankful and can’t say enough good things about Patty and her family, Ogie is a very shy dog and nervous and she did an amazing job welcoming him to her family, her dogs are pure love as well, she sent pictures and videos every day and kept us updated, we enjoyed the whole process and we will contact her again in the future, thank you so much! We feel very blessed!”
“Laura was great! She took our dog to the dog park three times over the span of her one night stay and she came back to us good and tired. Our dog really likes playing my with Pepper and Laura sent us lots of pictures, so we were never worried about her. Highly recommend!”
“Our little Franklin LOVES Miss Cindy! We know he is always in good hands with her. We love her too and she is now our go-to Rover for Franklin. I wouldn’t want to use anyone else!”
“Our boy Fenway just has his second stay with Evan and his wife. As I said previously, it's a very loving environment for a dog and Evan and his wife are true dog lovers. We will definitely be using them again!”
Loving dog boarding sitters in your neighborhood
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Erin & Chris R.Star Sitter
“Milli had a great weekend with Erin & Chris! They spoiled her while she was there! She also was very relaxed even after she returned home! I would definitely recommend them and appreciate that they limit the number of dogs at one time! Thanks Erin & Chris!”
Jessica V.Star Sitter
“Jessica was great with our dog Louie, loved the pics and vids during his stay. Booking and communication was easy and efficient. Highly Recommended, and many Thanks!”
Samantha W.Star Sitter
“Samantha was amazing!! I’m always hesitant to leave my fur baby with just anyone but Samantha gave us piece of mind and we were confident that he was well cared for! He had a ball and we have a new puppy sitter!!!”
Clare F.Star Sitter
“We needed a sitter at the last minute and Clare was able to take our little dog. I feel she took wonderful care of Chewey with ample walks and plenty of attention and sent pictures of a happy dog relaxing in the sun.”
Candace D.Star Sitter
“Very respectful and professional! Recommend 10/10. Response time was quick and comforting knowing our furry friend was going to a great family for the day!”
Alice b.Star Sitter
“Alice was an amazing sitter!! She sent me daily updates and my pup loved to play with hers. She was in constant communication and always answered. Thank you for watching my sweet boy!”
Cliff C.Star Sitter
“Cliff loved our dog well! We received pictures and videos while gone to see that she was in doggie Heaven while away! We have already rebooked. Thanks!”
Debora K.Star Sitter
“I boarded my little pomeranian with Deborah for a long weekend. She was great! She sent me a picture and messages every day of what Harley was doing. She is so friendly and we hit it off right away. I will definitely use her again for Harley.”
Lisa S.Star Sitter
“They took extra special care of Pause and made sure he felt at home. They even sent him home with an extra doggie bag of treats!! He is tired out from all the fun and will be staying over again in the future!”
Cory W.Star Sitter
“Lifesaver and LOVES animals. Never left my dog with anyone other than my mom and I didn’t feel nervous at all. Sent me pictures and played with blaze. BLAZE LOVED THE BIRDS 🤣🫶🏼”
Andrea G.
“Great person, great sitter. I've known her for years and she always shows so much love and care for all the dogs she meets. Her dedication to the safety and happiness of the dogs she looks over is truly admirable.”
Scott S.
“Tony had the best time and made lots of new friends!! Scott & Jess did such an amazing job taking care of our Tony, and we will definitely be using them again.”
Sherilynn G.
Star Sitter
“Sherilynn was great! First time using rover and someone non-family watching our dog. With her providing daily updates we were quickly comforted. We will use her again!”
Lara & Cary J.Star Sitter
“This was the second time Lara and Cary watched our pup. They were great as always and would absolutely recommend! They were flexible and very accommodating to our dog’s needs.”
Patricia ..
“We are so thankful and can’t say enough good things about Patty and her family, Ogie is a very shy dog and nervous and she did an amazing job welcoming him to her family, her dogs are pure love as well, she sent pictures and videos every day and kept us updated, we enjoyed the whole process and we will contact her again in the future, thank you so much! We feel very blessed!”
Laura B.
“Laura was great! She took our dog to the dog park three times over the span of her one night stay and she came back to us good and tired. Our dog really likes playing my with Pepper and Laura sent us lots of pictures, so we were never worried about her. Highly recommend!”
Lucinda W.Star Sitter
“Our little Franklin LOVES Miss Cindy! We know he is always in good hands with her. We love her too and she is now our go-to Rover for Franklin. I wouldn’t want to use anyone else!”
Melanie R.Star Sitter
“Melanie and family did great with Charlie! We received multiple pictures and updates throughout our vacation. Very nice family!”
Evan H.Star Sitter
“Our boy Fenway just has his second stay with Evan and his wife. As I said previously, it's a very loving environment for a dog and Evan and his wife are true dog lovers. We will definitely be using them again!”
Emma S.
“Did a great job with Titan. He had a great time and Emma spoiled him”
Over 84 pet parents in Winterset have booked dog boarding
Winterset dog parents share their Rover experiences
Popular requests near you
Select a filter and find qualifying Winterset sitters!How Rover works
1. Search
Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for dog boarding in Winterset is $40
Why Choose Rover?
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Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Winterset average 14 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, the median cost of dog boarding in Winterset is $40 per night, including service fees. Boarding your dog for one week typically costs $280. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Winterset dog boarding rates can be found as low as $17 to as high as $37 per night.
As of Aug 2025, 198 sitters provided dog boarding in Winterset. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple sitters about your booking. Typically, 89% of Winterset dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winterset have an average of 15 years of experience. Dog boarding sitters with repeat customers have an average of 14 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Winterset.
Rover makes it easy to find Winterset dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:
- Dogs of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their sitter’s pets
There are 198 dog boarding sitters in Winterset on Rover, so you’re sure to find the perfect match for your dog! In Winterset, 96% of sitters offer daily exercise, 96% offer medication administration, and 88% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog boarding sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
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