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.
“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.”
“Holly and her family are awesome. Sally and Sam really didn’t want to leave to come home. Holly kept me very up to date on what was going on with them. She sent photos also. I believe they had a great time and I will use Holly anytime we go on vacations.”
“Laura provided great care for my pup for a couple of days while we were traveling--doing boring people stuff--in her area; we received a happy (and tired) pooch at the conclusion of her stay. Would definitely book again!”
“Samantha does a wonderful job and my Golden Toby had a great nearly week long stay. She provides daily updates and sincerely cares about the well being of my dog.”
“I’m so happy I picked Tam and Alexander to watch our dog while we were out of town! The communication was great and I received so many pictures and updates. I would 100% recommend them and we will for sure use them again when we travel ☺️”
“We recently boarded our dog with Melanie and it was a great experience. Melanie and her family were so nice to work with and did a great with Maya. We liked getting updates and pictures while she stayed there. Highly recommended.”
“I am very appreciate of how Lucinda was attentive to my senior dog. She has a great fenced in yard that I know Bliss enjoyed. It was great to receive updates throughout his stay from Lucinda. Would definitely recommend to others!”
“This was our first booking and we were nervous. Candace and her family were absolutely amazing. Drop off and pick up were convenient and flexible. Lilo seemed to absolutely love his time with them. We got updates and pics of how he was doing, this certainly put our minds at ease. We booked Candace almost immediately again for our next trip because they left us so comfortable with their care of Lilo. We are so happy we found this family to care for our guy.”
“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.”
“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.”
“I think my Sam had a great time with Cynthia and family…and he was so lucky that Cynthia’s daughter was there with her little dog Reggie, so he had a playmate the whole time he was there (9days). Cynthia watered her plants outside and my Sam loves to be watered also. And with the very hot weather, he enjoyed it. Will be returning!”
About: I have had multiple pets from mice to dogs so I'm well rounded in diverse care. I love to play with animals especially dogs theyre just amazing. Weekends, work days, holidays (if needed). I can house for multiple days. I only leave to get groceries or to take my dog to the park. Safe and loving. Will have a great play partner Sammy loves to play he would all day if he could, we go on walks, park trips, sometimes just a drive.
“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.🥰”
“Our pup LOVED hanging out with Jill and her family! They treated him like their own and knew exactly how to make him feel comfortable and settle in. We received updates throughout his stay which really helped our peace of mind. We will definitely book again!”
“Ginny was a life saver. I needed someone to watch my dog on short notice. Ginny was responsive and super easy to make a plan with. My dog had a great time, I could tell from the photo updates during his stay and when I picked him up he was happy as could be. I know he got a ton of energy out with Ginny and her pups which is just what he needed. Thank you, Ginny!”
“Erin and Chris are amazing!! They were super responsive. Genuinely listened to all of my dog mom concerns and were gracious and accommodating!! I got lots of pictures with updates and reassurance that everything was going well!! I will absolutely rebook with them when I have future needs!!”
“Lara and Cary were so great with our dog, Nola! It was our first time leaving her after an incident at a local kennel this summer so we were worried and anxious. They sent several photos and updates and put our minds at ease. She had a nice, relaxing stay and we will definitely use them again and again!!”
“Alice is a Frenchie whisperer! Seriously, if you have French Bulldogs, stop your search and book her NOW. She swooped in last-minute and saved the day, taking amazing care of our two boys for 5 nights!! They were absolutely spoiled (which we fully endorse!) and had a blast playing with her adorable Frenchie. It's like they went on a little Frenchie vacation! Alice is incredibly sweet and we could tell our pups adored her. We'll be booking her again!”
“Stefanie and her fur babies took great care of Wilbur while making him feel comfy and loved. He was calm and happy after the experience, as was I. I trust that Wilbur is in good hands with her.”
The median cost per night for dog boarding in Winterset is $40
Dog parents share their Rover experiences - Winterset
Leaving your pets can be tough, but Debora made it completely stress free. She took care of my two dogs as if they were their own, providing a caring, comfortable environment. Her experience and patience with elderly dogs is wonderful to see. Debora is such a nice, kind person. I can't recommend them enough!
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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