Dog Boarding Hillside
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Hillside, 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.
“This was our first time using Rover, and we couldn't have asked for a better experience. Sarah accommodated our last-minute request to watch our 3-month-old puppy for two days. Rip and Mayla were so friendly and playful when we stopped by for a meet and greet. And Sarah's obvious expertise and calm demeanor made it clear that this was a good fit for us. She was always quick with responses, sent daily updates with several pictures spanning the course of the day, and gave a very thorough rundown of how our puppy did his entire time there when we arrived to pick him up. It was clear that she had his best interests at heart. And any time we need a puppy sitter, she will be the first person we contact. 10/10 Highly recommend.”
“Such a treat to have Duane & Lauren take care of my pup, Rapha while I was away. They are very responsive and attentive to the needs of both owner and doggie. Thank you!”
“Great communication for booking, through their stay, and when we needed to adjust our pick up time. We received pictures of our ladies several times, which brightened our day and helped us feel at ease when we were away. They were very attentive to the different food and medication needs our ladies have. We will definitely use them again for future boarding.”
“Lucy had a great weekend with Jennifer! She got along great with Oscar. Tick season is pretty bad this year and Jennifer made sure to look over Lucy and keep her tick-free!”
“Ronalisa did wonderfully! Floyd is high energy and can be pushy- so at first I was worried as we had never boarded through Rover before. But it was quickly apparent than Rona was confident and capable even with young and crazy dogs like Floyd. She always got back to me quickly and sent the cutest videos of them playing fetch, swimming, and hiking around. Her dogs are also great too! They helped Floyd play appropriately but still have fun. I would love to board with Rona again”
“We love Margaret & so does our pup, she’s at ease whenever she gets to the house and sees her favorite dog sitter. She’s the only Rover we choose and we couldn’t be happier with her excellent care!”
“Stacy welcomed my dog into her house and treated him as her own. Rudy loved playing and snuggling with her family! She communicated well and made sure she understood his needs. I will use Stacy again.”
“We had a wonderful experience! This family took excellent care of our mini goldendoodle while we were on vacation—so kind, attentive, and thoughtful. They sent plenty of pictures and updates, which gave us total peace of mind and showed he was happy and having fun. Highly recommend!”
“David was/is amazing! Why? He was responsive and accommodating. His extensive knowledge of dogs was clear when we met him - we knew our pups were in good hands. We received daily updates and in each photo the dogs looked like they were having the time of their lives and/or taking a nap on David’s lap 😂. We live downtown Madison and I could tell our pups enjoyed the beautiful country property as they came back tired and content! As a former Rover, I would highly recommend David to anyone looking for a sitter. 10/10!!”
“Sarah was wonderful with Jake and Meme while we were away for a couple of days! She had great communication, kept us updated, and did a fantastic job picking up on their individual cues and personalities. It gave us peace of mind knowing they were in good hands. Thanks so much for taking such great care of them, Sarah! We really appreciate everything!”
“Angelica was fantastic! She took care of our dog with lots of love. Took her out for walks and played with her. Also fed her well and followed our dog diet restriction. Definitely we will contact Angelica again! Angelica fue fantástica! Cuidó muy bien de nuestra perra con mucho cariño. La sacó a caminar y jugó con ella. Fue muy atenta al seguir al pie de la letra el regimen alimenticio que nuestra perra debía tener. Definitivamente, volveremos a contactar a Angelica!”
“Mary and her family were absolutely wonderful sitters for Grizzy! They took great care of him during a cold snap, making sure he was warm and comfortable. Mary sent wonderful updates and absolutely adorable pictures, and I would recommend her to anyone!”
The median cost per night for dog boarding in Hillside is $45
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.
How to book dog boarding
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 for dog boarding - Hillside
Select a filter and find qualifying sitters offering dog boarding.Sitters in Hillside average 10 repeat dog boarding clients
FAQs for Dog Boarding - Hillside
Frequently asked questions about Rover
As of November 2026, there are 522 sitters on Rover offering Dog Boarding across Hillside. Enter your ZIP code to see which available sitters are closest to your home.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.
94% of sitters in Hillside can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.
During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.
Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Hillside 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 Hillside.
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.
Yes, you can find sitters who have experience with handling special pet needs in Hillside. On Rover:
- 88% of sitters can help with special care needs
- 96% can help with giving oral medications or injections
- 94% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
You and your Hillside 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 WI 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.
Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.
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