Dog Boarding Hillside

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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.

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Sitter Profile Image: Jessica P.
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Jessica P.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 16 reviews
3 repeat clients
30 years of experience
FORT ATKINSON, WI, 53538

“5 stars!! ⭐️ 🌟 🌟 💫 ⭐️ Jessica is amazing! She graciously dealt with our uncertain and hetic schedules. She went over and above, driving to my home to pick my dog up. Even when he was initially bashful/scared, she waited and took extra time. Gave him extra love and care, car rides, treats, and nap time together. I felt he was safe, content, and at ease while in Jessica’s home. We will definitely be hiring her again!!”

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Cindy P.
Sitter Profile Image: Sarah S.
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Sarah S.
from
$45
per night
5.0 out of 5 stars
• 63 reviews
12 repeat clients
25 years of experience
Edgerton, WI, 53534

“Clover had an awesome time with Sarah and her pups. This was our first time using Rover and Sarah made us super comfortable with the process. She was very fast with responses, and sent updates and photos while we were away. Her dogs were very friendly with us and made quick friends with Clover. Would recommend to anyone, and will definitely use again.”

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Jess O.
Sitter Profile Image: Duane & Lauren S.
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Duane & Lauren S.
Star Sitter
from
$32
per night
5.0 out of 5 stars
• 95 reviews
31 repeat clients
30 years of experience
Ridgewood, Madison, WI, 53704

“Duane and Lauren were wonderful to work with and took great care of our two dogs!!! Their communication was terrific and they were very flexible. We would love to have our dogs stay with them again!!”

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Dave W.
Sitter Profile Image: Amanda K.
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Amanda K.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 197 reviews
65 repeat clients
20 years of experience
Cottage Grove, WI, 53527

“Our dog simba had a great stay with Amanda and her family. We loved getting updates and pictures of how he’s doing. Definitely will be using her again next time we’re away. Thank you!”

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Marta M.
Sitter Profile Image: Jennifer J.
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Jennifer J.
Star Sitter
from
$37
per night
5.0 out of 5 stars
• 8 reviews
5 repeat clients
6 years of experience
Lake Edge, Madison, WI, 53716

“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!”

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Chuck S.
Sitter Profile Image: Ellen S.
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Ellen S.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 63 reviews
18 repeat clients
10 years of experience
Marshall, WI, 53559

“Highly highly recommend Ellen! Our pup had the best time; we could tell immediately she would love him like we do. Great backyard, lots of updates and a very tired pup from so much play when we got home. We will definitely work with Ellen again!”

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Josh H.
Sitter Profile Image: Kaycee & Robert R.
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Kaycee & Robert R.
Star Sitter
from
$36
per night
5.0 out of 5 stars
• 39 reviews
6 repeat clients
16 years of experience
Heritage Heights, Madison, WI, 53714

“Kaycee and Robert did a great job with our little puppy Milton. We loved that Milton could play with their kids, run around in the backyard with their dog, and feel at home. He’s a handful and came home happy!”

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Jill B.
Sitter Profile Image: Kristin & Bruce M.
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Kristin & Bruce M.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 111 reviews
31 repeat clients
2 years of experience
Madison, WI, 53719

“Cricket has been staying with Kristin, Bruce, Hartley, and Lauren for some time now, and we have nothing but the best things to say about his stays. He always looks over the back seat on the way home because I think he misses them already! My last trip, my flight was delayed on the way back, and even though they had their own plans, Kristin and Bruce were super flexible and accommodating with pick up. Cricket has another stay coming up and we can't wait.”

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Ali Y.
Sitter Profile Image: Jessica M.
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Jessica M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 49 reviews
13 repeat clients
25 years of experience
Rolling Meadows, Madison, WI, 53714

“Jessica was great again. Understood that my dog like to try to escape and kept him safe and his tracking collar charged. I got pictures and updates everyday, I’d use her whenever she’s available!”

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Emily G.
Sitter Profile Image: LAVAL [VAL] S.
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LAVAL [VAL] S.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 286 reviews
151 repeat clients
30 years of experience
Sun Prairie, WI, 53590

“I had a great experience with our Rover sitters Val & Sherri) while I was away for a week. They took excellent care of Phoenix, kept me updated with photos and messages, and gave me peace of mind knowing he was in good hands. Phoenix came home happy, healthy, and clearly well cared for. I really appreciated their professionalism, communication, and genuine love for animals. I would definitely trust them with Phoenix again and highly recommend them to anyone looking for dependable pet care!”

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Anywhere-Fitness
Sitter Profile Image: Stacy L.
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Stacy L.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 88 reviews
6 repeat clients
30 years of experience
Janesville, WI, 53546

“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.”

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J D.
Sitter Profile Image: Heather W.
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Heather W.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 40 reviews
10 repeat clients
20 years of experience
Brooklyn, WI, 53521

“Heather took fantastic care of our dog while we were away. She sent us pictures and updates and made sure our dog got outside to enjoy plenty of exercise. It felt like our pup was part of her family. I would highly recommend reaching out to Heather if you’re looking for a quality Rover!”

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James H.
Sitter Profile Image: Mattison & Eli H.
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Mattison & Eli H.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 20 reviews
8 repeat clients
15 years of experience
Madison, WI, 53718

“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.”

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Cole O.
Sitter Profile Image: Brandon & Katy S.
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Brandon & Katy S.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 10 reviews
4 repeat clients
15 years of experience
Worthington Park, Madison, WI, 53714

“Brandon and Katy are lovely! They were very helpful moving my dog's crate and getting him settled. Sammy had a great time playing and cuddling.”

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Kara B.
Sitter Profile Image: Edith S.
Verified Enhanced Background Check
Edith S.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 86 reviews
27 repeat clients
20 years of experience
Waunakee, WI, 53597

“Edith did a great job watching my dog, again! She provided daily updates and lots of pictures. I could rest easy on my vacation knowing my dog was well cared for.”

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Jennifer D.
Sitter Profile Image: Stephanie E.
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Stephanie E.
Star Sitter
from
$42
per night
5.0 out of 5 stars
• 30 reviews
11 repeat clients
18 years of experience
Madison, WI, 53704

“We are so grateful to have found Stephanie to watch our two highly energetic golden girls! She gave them lots of play time, exercise, and snuggles on the couch. She was kind, patient, and easy to communicate with. Highly recommend and we would love to bring our dogs back to her 🥰”

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Christina Z.
Sitter Profile Image: Chelssey H.
Verified Enhanced Background Check
Chelssey H.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 27 reviews
12 repeat clients
16 years of experience
Madison, WI, 53711

“Chelssey was awesome! Great communication prior and during Sunny’s stay which I loved! She also sent pictures which was fun. We will book again with Chelssey.”

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Carol D.
Sitter Profile Image: Sarah M.
Verified Enhanced Background Check
Sarah M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 126 reviews
18 repeat clients
35 years of experience
Deforest, WI, 53532

“Our 2 dogs stayed at Sarah's for about a week earlier this month. The stay was great! We got daily updates, including photos and videos. They have a fantastic large fenced in yard where they could safety run and play. They had lots of playtime, but also lots of snuggles and love. They were both clearly enjoying their own vacation at Sarah's while we were gone on ours. It was so refreshing to know they were so well cared for while we were away- we have already rebooked them for our next trip!”

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Lisa W.
Sitter Profile Image: Tessa S.
Verified Enhanced Background Check
Tessa S.
from
$35
per night
5.0 out of 5 stars
• 20 reviews
7 repeat clients
7 years of experience
Fitchburg, WI, 53711

“Tessa was great! She was well prepared, introduced dogs in a calm way and scheduled a meet and greet at a dog park so she could watch our dogs interact. Overall very thoughtful!!”

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Aditi R.
Sitter Profile Image: Emily V.
Verified Enhanced Background Check
Emily V.
from
$50
per night
5.0 out of 5 stars
• 20 reviews
6 repeat clients
18 years of experience
Oregon, WI, 53575

“Emily was great with our big, young and very energetic dog! She has a great fenced in yard and our dog had a blast! He was very tired when he got home! We would definitely use her again!”

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Eric & Christine A.
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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. 1. Search

    Browse profiles of sitters near you who offer dog boarding.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
  3. 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.

FAQs for Dog Boarding - Hillside

Frequently asked questions about Rover

Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.

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.

Depending on the sitter, their home environment, and your dog’s needs, daily exercise 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.

<b>Tip:</b> 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 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.

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