Dog Boarding Cheeseville

Find a loving dog sitter to watch your dog overnight at your sitter's home.

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Over 12
pet parents in Cheeseville have booked dog boarding

Cheeseville, 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.

1 / 1
Sitter Profile Image: Gilian S.
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Gilian S.
from
$35
per night
5.0 out of 5 stars
• 241 reviews
61 repeat clients
9 years of experience
Saukville, WI, 53080

“Olive loves staying with Gilian. She gives the dogs a lot of attention and really cares for them. She is reliable, attentive, and very friendly. I cannot recommend her enough”

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Emily S.
Sitter Profile Image: Diane & Dale G.
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Diane & Dale G.
from
$37
per night
5.0 out of 5 stars
• 15 reviews
2 repeat clients
30 years of experience
Random Lake, WI, 53075

“Diane and Dale went above and beyond to accommodate our schedule and care for Oliver. He fit right in with their dog, Lexi, enjoyed the walks around the pond and was well-loved. I highly recommend them!”

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Pamela B.
Sitter Profile Image: Karen M.
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Karen M.
Star Sitter
from
$44
per night
5.0 out of 5 stars
• 14 reviews
5 repeat clients
9 years of experience
Plymouth, WI, 53073

“Karen was fantastic with Dottie! She sent us an update and photo each day and loved our dog as her own. I would definitely have her watch our dog again.”

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Haley P.
Sitter Profile Image: Amanda C.
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Amanda C.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 16 reviews
6 repeat clients
18 years of experience
Germantown, WI, 53022

“Amanda was wonderful. She took such good care of my dog and sent me lots of updates throughout his stay. She was super flexible and easy to get ahold of the entire time!”

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Alexandra M.
Sitter Profile Image: Ashley M.
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Ashley M.
from
$45
per night
5.0 out of 5 stars
• 18 reviews
6 repeat clients
15 years of experience
Capitol Heights, Milwaukee, WI, 53218

“Ashley was an amazing dog sitter for our pup! She communicated throughout the stay, sent pictures, and made him feel at home! I highly recommend! Thank you for the experience!”

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Makalia P.
Sitter Profile Image: Angela K.
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Angela K.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 152 reviews
38 repeat clients
25 years of experience
Menomonee Falls, WI, 53051

“Angela was amazing! She was flexible with drop off/pick up, sent us pictures/videos of our Olive. I felt very comfortable having our dog stay with her and her family. Will definitely use again in the future when we go out of town. Thank you!!!”

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Jennifer C.
Sitter Profile Image: Paul S.
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Paul S.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 111 reviews
40 repeat clients
20 years of experience
Germantown, WI, 53022

“Paul did an amazing job watching our pup! He "warned' us that he would try to exceed our expectations, and no question he absolutely did. We loved all the updates with photos, and the numerous offsite visits to parks was so fun to see. So comforting while we were such a long distance away. We'd recommend Paul to anyone!”

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Steve N.
Sitter Profile Image: Maria & Nayibe B.
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Maria & Nayibe B.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 438 reviews
142 repeat clients
20 years of experience
Menomonee Falls, WI, 53051

“I cannot say enough about Maria and Nayibe. I’m very selective about who I allow to care for my dog and I can 100% say that I made a good choice. Throughout the weekend, I received updates, pictures and video which really put my mind at ease. Thank you so much and I will be using them again!”

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Andrea W.
Sitter Profile Image: Sherry Z.
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Sherry Z.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 52 reviews
13 repeat clients
30 years of experience
Pheasant Run, Milwaukee, WI, 53224

“Sherry was wonderful with Nukka! She provided updates regularly, gave Nukka lots of love and walks. When a slight health issue arose, Sherry immediately notified me so I was aware of what she was seeing. I was able to get Nukka into the vet the following day for treatment! Thanks for taking such good care of our girl!!”

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Tori S.
Sitter Profile Image: Judy & Paul & Melissa P.
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Judy & Paul & Melissa P.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 415 reviews
145 repeat clients
20 years of experience
Sheboygan, WI, 53081

“Judy is always responsive when we check in! She sends a ton of photos showing how much fun Raider is having; and quickly lets us know when something negative happens. We will use her again and again!”

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Ryan B.
Sitter Profile Image: Christine M.
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Christine M.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 216 reviews
68 repeat clients
25 years of experience
Cedarburg, WI, 53012

“Christine and her husband were great. Our dog had a good time and was so tired out when we picked her up. They sent pictures each day and kept us up to date. Thank you again!”

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Anne S.
Sitter Profile Image: Shay C.
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Shay C.
from
$50
per night
5.0 out of 5 stars
• 38 reviews
7 repeat clients
20 years of experience
Cedarburg, WI, 53012

“So wonderful to know our little guy is in such good hands! Shay is warm and kind, and Gatsby is a fantastic new friend. We are so happy to know that we’ve found such a great “summer camp” while we’re away.”

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Nadia N.
Sitter Profile Image: Laura R.
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Laura R.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 22 reviews
8 repeat clients
15 years of experience
Sheboygan, WI, 53081

“We could not have been happier with the care that Laura and her family provided for our 2-year-old Black Lab, Jewel, while we were in New York for five days. Laura checked in regularly and shared funny photos of Jewel clearly living her best life! Laura and her family went above and beyond—they even set up a small plastic pool, which Jewel seemed to thoroughly enjoy, along with plenty of playtime and frolicking with the children. Their fenced-in yard and quiet neighborhood provided a safe and welcoming environment. When our return flight was unexpectedly canceled and we needed to stay an extra day in New York, Laura was incredibly accommodating and flexible. We felt completely at ease knowing Jewel was in such good hands. I highly recommend Laura and her family to anyone looking for loving, reliable, and attentive pet care.”

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Dave B.
Sitter Profile Image: Emma S.
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Emma S.
from
$40
per night
5.0 out of 5 stars
• 62 reviews
22 repeat clients
15 years of experience
Fond du Lac, WI, 54935

“My dogs stayed with Emma for one night while we were in town for a wedding. We were coming from out of town and had to change our arrival time more than once. Emma was very particular with us! 😀”

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Carrie J.
Sitter Profile Image: Cindy T.
Verified Background Check
Cindy T.
Star Sitter
from
$55
per night
4.9 out of 5 stars
• 615 reviews
364 repeat clients
30 years of experience
Wauwatosa, WI, 53222

“I felt completely comfortable that my dog was in caring and capable hands! Cindy sent a lot of pictures and kept me informed in regard to my dogs’ stay. Will definitely use her services again! Highly recommend.”

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Meredith W.
Sitter Profile Image: April P.
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April P.
from
$50
per night
5.0 out of 5 stars
• 9 reviews
20 years of experience
Slinger, WI, 53086

“April and family were amazing! I was nervous at first, however quickly was at ease with all the updates and photos I received. They treated Allie like family and she looked so happy hanging out with them I wasn’t sure she would want to come home! Hahaha”

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Cassandra H.
Sitter Profile Image: Mary & Hanna S.
Verified Background Check
Mary & Hanna S.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 149 reviews
67 repeat clients
11 years of experience
Sussex, WI, 53089

“Our dog had the best time at Mary’s home for the weekend! I really appreciated the communication, photos, and updates. Made us feel super comfortable leaving our dog in such great hands!”

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Sara K.
Sitter Profile Image: Cyen B.
Verified Enhanced Background Check
Cyen B.
from
$50
per night
4.9 out of 5 stars
• 24 reviews
6 repeat clients
10 years of experience
West bend, WI, 53095

“Cyen was great at communicating with us and taking care of the needs of our dog. I enjoyed the updates and photos during our pet's stay too!”

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Mary K.
Sitter Profile Image: Kelly L.
Verified Background Check
Kelly L.
from
$26
per night
5.0 out of 5 stars
• 9 reviews
6 repeat clients
5 years of experience
SHEBOYGAN FALLS, WI, 53085

“Kelly took care of our Rocky so well. Rocky had a bit of a health concern that we were able to resolve over the phone without going to the vet, but she was ready to go if need be. That meant a lot to me. I would highly recommend her.”

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Peggy L.
Sitter Profile Image: Frank C.
Verified Enhanced Background Check
Frank C.
from
$35
per night
5.0 out of 5 stars
• 15 reviews
5 repeat clients
1 year of experience
Cambridge Heights, Milwaukee, WI, 53211

“My anxious dog settled in beautifully with Frank and his two little dogs, allowing me to enjoy a worry-free two week vacation. Frank sent updates with photos which greatly reassured me that all was going even better than hoped. Honey clearly enjoyed a relaxing time with Frank in his home and made new friends with his dogs. I highly recommend Frank and would not hesitate to rebook with him!”

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Tracy H.
1 / 1
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The median cost per night for dog boarding in Cheeseville is $45

Dog parents share their Rover experiences - Cheeseville

1 / 1
5.0 out of 5 stars

Loved having my sweet baby stay with Cody! He is very kind and attentive. We loved how well he took care of our dog 😊 would give her tons of cuddles and took her on long daily walks which she loved! Very quick response time and provided us with daily updates with pictures and videos. Will definitely be booking with him again in the near future!

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Maddie M.
Boarding
5.0 out of 5 stars

Cody was so great! He communicated well, sent pictures and videos with updates, and gave my dog lots of love while I was away. He also was able to accommodate last minute changes in plans which helped us out so much. Definitely recommend him!

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Nicole K.
Boarding
5.0 out of 5 stars

Cody was very great with my pup he kept us updated on our dogs progress and everything sent pictures etccc my pup came back just as happy as when he left he was so great with our Rep we really appreciate him

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Shada S.
Boarding
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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 - Cheeseville

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Sitters in Cheeseville average 12
repeat dog boarding clients

FAQs for Dog Boarding - Cheeseville

Frequently asked questions about Rover

The average cost of Dog Boarding in Cheeseville is $40 per night as of November 2026. Most bookings cost between $33 and $44 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of November 2026, there are 655 sitters on Rover offering Dog Boarding across Cheeseville. 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.

93% of sitters in Cheeseville 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 Cheeseville 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 Cheeseville.

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 Cheeseville. On Rover:

  • 89% of sitters can help with special care needs
  • 95% can help with giving oral medications or injections
  • 93% 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 Cheeseville 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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