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
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Deb took great care of Oscar while I was away. He was recovering from a knee surgery, on medication and I was very nervous using a new pet sitter. She put my mind at ease and was very inventive and found ways to let him quietly play and stay entertained.”
“Absolutely recommend. She kept us updated on our babies and was always quick to answer when I checked on them. She sent pics of the girls at dogpark and took many pics during the girls visit. She was absolutely amazing!”
“Kylie and her family were phenomenal! My pup felt right at home with her 2 other dogs - who are the sweetest and well behaved. Kylie was so great and sent photos daily to show how happy and just how much she was being loved on!! Would recommend her to all for anyone needing a loving stay-cation for their dog🙂”
“Finley seemed to have a great time with Samantha and her family. He is often sad when we leave him and doesn’t eat and apparently that wasn’t the case. I greatly appreciated the pictures.”
“Melanie and family took care of Maxim for more than a week like a family. They shared updates regularly and were very caring. We are so happy and would definitely recommend them.”
“Erin & Chris are great & took care of our doodles like they were their own. Tons of pictures all weekend to keep us updated! Will definitely be using them again in the future!”
“Candace and her husband took great care of our Layla! She kept us updated with pics and it sounded like their dog got along great with ours❤️ We knew she was in great hands all weekend!”
“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!”
“This was my first time using Rover and I was pleased with Jessica’s quick response time and enthusiasm to meet and care for Blanca. The process was easy and drop off went smoothly. Jessica’s dog was in a kennel when we arrived to make drop off less stressful for both dogs. The pups were introduced after we left to get their sniffing done on neutral territory (on a walk out front). We received photos and updates during our whole time away and knew Blanca was happy and safe. We would be happy to use Jessica again in the future!”
“I always book Alice to look after my Frenchie. She is so communicative and loves my dog like her own. I know he is in the best hands whenever I drop him off.”
“Scott and Jessica took great care of our Lady! The communication was much appreciated when we missed her so! Lady has really benefitted from their attention to her extra needs. We will definitely Rover with Scott and Jessica again!”
“Angela and Dan provided amazing care for our dog, Thunder. They loved him as their own! They sent us updates and pics and made us feel very comfortable. They were very flexible with pick up and drop off. I can’t recommend them enough!”
“Our dog always gets excited to go to Cliff’s and that makes it so much easier to leave her. We know she is well cared for there. We also love the updates Cliff provides us with during her stay.”
About: I grew up with dogs and now have 2 cats and 1 dog of my own! Our cats are both American Shorthair and our dog is a golden retriever! My husband and I both work full time but can be home if needed. We also have weekends off so can give all the attention during that time. I have two very friendly cats who warm up quickly to other animals or hide until they feel comfortable! We also have a golden retriever who loves other animals and loves to play! I live in house with a fenced in backyard!
“Lucia was fantastic with my puppy! She sent updates and followed all of Shelby's instructions. Lucia even took Shelby to the park to play! Shelby was happy and healthy when we got home. 10/10 would book again!!”
About: Experienced pet care professional with fenced in yard and acreage. Prior experience with many different pets in different stages of life. Have been boarding dogs on routine basis for 10+ years I love pets that come to visit or stay! Friends can play with my furry friends or play separately. I work a regular job m-f but am home afternoons, evenings and weekends. Exercise pens, crates and a fenced in yard are available. Pets are supervised when free roaming and are exercised several times a day. Can supervise puppies, elderly dogs or pets with some health issues.
“Had to drop my cat off somewhere for the day while work was being done on my apartment. First time ever leaving him somewhere. Drop off was easy and assured me he was in good hands. Wooo be doing again.”
Over 94 pet parents in Winterset have booked dog boarding
Winterset dog parents share their Rover experiences
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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
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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 Feb 2026, 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 $19 to as high as $37 per night.
As of Feb 2026, 196 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, 91% of Winterset dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winterset have an average of 16 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 196 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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