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♡♡♡♡♡”
“Holly and family were amazing. They boarded our two dogs for 12 days without any issues. Holly sent updates and photos every day and our dogs loved staying with her. We hope to do business with Holly every time we need a sitter!”
“Melanie was amazing with our dog Jack. She was available in a short period of time and so communicative. Her daughters were also great with him. He seemed so happy and loved his stay! Would stay again!”
“Samantha is amazing! My 3 year old Cavapoo loves staying at her home. I receive regular updates & photos which is what any pet owner could ask for. Thanks again Samantha!”
“Tam and her partner were exactly who you'd want to leave your fur baby with, and in my case, totally saved the day with a last minute booking. They were friendly, extremely responsive and from the pictures, my picky chihuahua had a great time. Would def book again!”
“Candace did a great job taking care of our Sadie while we were away on a trip. Great communication, shared multiple photos. Will not hesitate to book with Candace again in the future.”
“Our yorkie-poo LOVED Cindy! She was the perfect Rover for him. She spoiled him and treated him as her own fur baby. It was nice having a Rover who focuses her attention on one dog at a time in her home, so we didn’t need to worry about how he would interact with unfamiliar dogs. We felt very confident in her care and trusted her as she is a long term resident in the community. She also sent some cute pictures of our Franklin! Thank you, Cindy! Highly recommend especially for little dogs who need extra attention. We will definitely use Cindy again. 🐕🦺”
“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.🥰”
“Jessica did an excellent job with little B and he came home happy and healthy. He can’t settle down without his dog bed, so we were glad we could leave it with him. We also brought his food and water bowl. Jessica was professional, competent, and caring. Five star rating, for sure! We will definitely use her again.”
“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.”
“Kimberlee is wonderful! Our pup is a repeat customer of hers, and he didn’t even look back when we dropped him off. His tail was wagging the whole time! She sends lots of photos, and it’s clear your dog is in great hands with her. We’ll definitely be bringing our pup back!”
“We love Erin, Chris, and their family! They treat our dog, Bailey like their own. They are super easy to work with and I love knowing that Bailey is in a loving home while we are gone.”
“Angela and Dan were amazing. They treated Buddy like he was their own. I know he felt so safe and loved. He was tired when he came home because he had so much fun going on walks! I loved all of the pictures they sent!”
“Lisa continues to be awesome with my dogs. She notices behavior and offers suggestions as well. Love getting all the updates and pics so I feel comfortable with her care. As far as location, being close to the airport is a huge bonus.”
“Ally was really great with my dog Miller. She was very open with her communication and sent a lot of updates and pictures over the weekend. I would definitely recommend her to anyone looking for a dog sitter in the area. And will definitely let her watch my dog again in the future”
“Our dog had a blast with Tanya's family! She shared great photos and went out of her way to make sure our guy was well cared for during fireworks too. We will definitely use her again!”
“This was the second time we left Stormy with Evan. The first time was for two weeks and it worked out so well for us and Stormy and I did not hesitate to leave him again with Evan for a weekend. I appreciate the photos and updates Evan sent while we were gone, and Stormy seems to enjoy staying with him. ”
“We went to do a meet and greet with Shea a few weeks before Maisy stayed with Sheas family. The house was well kept and everyone was very friendly and welcoming. We will be making arrangements with Shea in the future for additional stays with Shea and her family. I could tell that Maisy felt very comfortable with them by how well she ate her food while staying with them. I highly recommend giving Shea the opportunity to care for you pet.”
The median cost per night for dog boarding in Winterset is $40
Dog parents share their Rover experiences - Winterset
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!
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
Browse profiles of sitters near you who offer dog boarding
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Winterset sitters!Sitters in Winterset average 13 repeat dog boarding clients
FAQs for Dog Boarding - Winterset
Frequently asked questions about Rover
The average cost for Dog Boarding in Winterset on Rover is $27.75 per night (as of July 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 July 2026, there are 278 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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