Dog Boarding Winterset
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 66 pet parents in Winterset have booked dog boarding
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.
“As always, Deborah is Awesome! I can tell Harley loves being with her. He's perfectly at home. I don't know what I would do without her! Thanks for another great stay, Deborah♡♡♡♡♡”
“Cynthia was so easy to work with and was flexible to do a last minute booking. They were so sweet and have a great environment for out. My pup left happy, we will definitely be back!”
“Holly was so kind it was first time i left my dogs she sent pics and let me know how they were. They seemd to love it there. I would recommend her to anyone needs a dog sitter”
“Ivana treated Max like he was her family. He was happy feeling part of the team with her dogs. He was pampered and loved. I will definitely use Ivana again.. so satisfied with her care for Max.🥰”
“Great experience with Spencer and Candace taking care of my dog. They were very nice, helpful, and always responded quickly. I also really appreciated how flexible they were when I had to change the time last minute. I would definitely recommend them!”
“Melanie and family were wonderful. We had so much peace of mind having our 2 small dogs in their care for our 2+ week trip to Europe. They did a great job updating us and sending pictures. 5 stars all around!!! We look forward to booking with them again in the future. :)”
“My dogs were so relaxed when we came to get them after 6 days. Laurie sent pictures to keep us updated on how they were doing. This helped us enjoy our time away from them. She was so kind. I would highly recommend her!”
“Lara and Cary provided Bear the home away from home that he needed while we were away. Lara sent pictures of Bear reassuring us that he was the king of the castle at yet another house. They enjoyed him and pampered him. Quite a treat for our older dog who can be a bit grumpy with his new playful younger sister, Sadie Mae.”
“Cliff was amazing with Daisy! He made her feel right at home very quickly. She stayed for several days and was so excited to see him and the other pups after the first day. We couldn’t have asked for a better experience and would definitely recommend Cliff. He treated Daisy like one of his own, sent pics and updates throughout her stay.”
“Becky took care of Silky very well and took him for walks and updated regularly regarding how he was doing. She also picked him up and dropped him off which was very convenient especially with the bad weather with snow at the time.”
“Butter loved her stay at Ashly’s! Ashly is a professional and we felt instantly comfortable when dropping Butter off. Ashly did a great job following all of our care instructions. Butter had a great time playing with Ashly’s dog and definitely needed a bath from all the fun after we picked her up! Would definitely use Ashly’s services again. Thank you so much!”
“Jessica watched Tripper for us during our most recent trip out of town. It was our first time boarding Tripper anywhere, and he had a blast. He met and played with her dog Rip and cat Ghost as well as the other dogs she watched during his 5-day stay. He came home tired and happy. She communicated and was flexible with drop-off and pick-up, and sent us updates to let us know how Tripper was doing. We would absolutely love to board with her again. We highly recommend her!”
“Evan and his family took good care of Scout. He was happy, well-fed, and comfortable. I was a bit worried to leave him with a new sitter for a full week but my fears were unfounded. I will certainly have Evan take care of Scout in the future.”
“Awesome Awesome Awesome 5 ⭐ If I could give more I would 😊 They did amazing...very attentive... understanding, they sent videos and pictures, communicated with us on how he was doing morning and night...Kimberlee and Mitchell understood the assignment...We had a problem with a previous Rover sitter and we really wasn't sure if we wanted to do this again but I'm glad we did because they were Awesome...We will definitely book with them in the future and if you have a fur baby and he is needy/separation anxiety go with them...there were other dogs around to help put his mind at ease (I didn't get any bad reviews) Again 5 ⭐ Don't hesitate 😊”
“Only positive things to say, whether it’s communication or how caring she is of our dog and other dogs in her care. Our dog can’t get out of the car fast enough when we get to her house, the truth is in the tail wags, he loves staying with Elizabeth!”
“Alice is absolutely amazing ! As soon as we dropped Benji off, we felt like he was in the best hands! This was one of the first times we were away from him this long and Alice made us feel so at ease and reassured throughout the whole trip! I’ve found a permanent dog-sitter in Alice ! I highly recommend and appreciate you, Alice ! Thank you for everything !!”
“Awesome experience! I was nervous about leaving my dog with someone outside of family for the first time, especially for an extended period. Mackenzie and Anthony did a fantastic job keeping us updated, sending lots of pictures and videos while we were away. They're genuine, dog-loving people who truly want your pup to have a great time in your absence. Highly recommend!”
“Always takes great care of our dog! They are very active and quick to answer any questions I may have and are always sure to send pictures. Pua has so much fun there.”
“Sadie enjoyed her stay with Lisa so much, I'm not sure she wanted to come home! She even had her own Thanksgiving dinner. We appreciated the pictures and updates during her stay. Thanks!”
The median cost per night for dog boarding in Winterset is $40
Dog parents share their Rover experiences - Winterset
Debora, Is a very nice lady. I knew the minute we got out of the car, I found Alleys person. She left me in the wind and ran up to Debora. She was not timid and walked in like she had been there a 1K times. Debora, is very detailed, ask questions and always updates. Originally it was just a few days overnight. I definitely will e here again.
Debora gave wonderful care to our little boy (a Chihuahua) for the 9 days we were away on a trip. We received several pictures and emails from Debora while we were away, showing how he had settled in and was very comfortable with her at her house. We had a great time on our trip as well, knowing he was so well cared for with her. Thank you again, Debora!
Laura is AMAZING! Our Lillie has found a home away from home. Laura sent updates and pictures during the week. She even let our girl sleep with her during a thunderstorm! We plan to use Laura again and again. We are so thankful we've found a person we trust when we are away.
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
Book and pay through Rover’s secured platform—no cash or checks required.
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
1. Search
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Popular requests for dog boarding - Winterset
Select a filter and find qualifying sitters offering dog boarding.Sitters in Winterset average 12 repeat dog boarding clients
FAQs for Boarding - Winterset
Frequently asked questions about Rover
The average cost for Dog Boarding in Winterset on Rover is $27.9 per night (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Boarding easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Boarding. For more information on service fees, click here .
As of August 2026, there are 258 sitters on Rover offering Dog Boarding across Winterset. Enter your ZIP code to see which available sitters are closest to your home.
Every sitter on Rover has their own rhythm and routine, but most will follow the flow that keeps your dog happiest. Sitters can give meals on your dog's regular schedule, provide a comfortable place for sleep, and plenty of one-on-one attention.
94% of Winterset sitters also include daily walks in the neighborhood during dog boarding stays. You can also request photo and message updates throughout the stay so you can see which Winterset landmarks or neighborhoods your dog is enjoying.
If your dog is a little shy, consider booking a one-night trial stay! This practice run can boost your and your dog’s confidence before your trip.
Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Winterset home-away-from-home, we recommend packing:
- Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
- Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
- Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Winterset.
Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.
You and your Winterset sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.
Many sitters in IA ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.
By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
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