Dog Boarding Oconomowoc
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 292 pet parents in Oconomowoc have booked dog boarding
Oconomowoc, 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.
“Our puppy Luca had such a great time with Heather and her family! We could have not asked for better care for our boy! Heather was so attentive to Lucas needs and how to keep him active, engaged, and happy. We received lots of pictures and videos while we were gone giving us peace of mind. Luca loved playing with the family dog and even had extra pup company while enjoying a beautiful evening outside by the fire. We will absolutely have Heather and her family sit for us again!”
“Jenifer is amazing! I’d never used Rover before, or had my pup stay with anyone other than my close friend. Since we were getting married, we needed to find a sitter for a couple nights and after seeing the very many good reviews about Jenifer, I thought I’d give it a shot and I’m so glad we did! She obviously loves dogs- dropping our pup off was easy since she had 2 huge baskets of toys for her to get excited over! She sent us pictures of our pup every day and was altogether reassuring and great. I’d do it again in a heartbeat- it’s so nice to know we have someone nearby we can trust with our baby!”
“Our old man has such a great time here! This was his second stay and he was pooped when he came home from all the fun he had. Maria and Nayibe treated him like a family member and kept us up to date on how he was doing the whole time. Definitely recommend and will definitely be back. ☺️”
“Cheryl and Josh were great with our dog, Goldie. She got a lot of walks and we know she got a lot of attention and love. She came home exhausted. 😅 We will definitely trust Cheryl and Josh again for future dog watching!”
“Ms. Monique gave Ned an incredible vacation while we were away! His stay was exactly what we were looking for: a loving home away from home. Monique was incredibly welcoming and accommodating, has a great way with animals, and the perfect setup both inside and out. Monique was incredibly responsive and we so enjoyed the updates while we were away :) Ned is already counting down the ways until our next trip back, thank you again!”
“Gracie had an amazing stay with Joanne (& her family!) I enjoyed the communications and pictures during Gracie’s time in their home. Gracie enjoyed playtime with the kids and with the resident dog, Olivia. She had her kennel available, but enjoyed cuddles with their teenage son and quickly made herself a part of the family. I will certainly consider booking for future stays, and recommend Joanne to others!”
“Nina has stayed with her twice now, and both experiences have been absolutely wonderful. She treats Nina with so much love, patience, and care that I always have complete peace of mind while I’m away. I always receive updates and photos, and it is clear that Nina is happy, safe, and loved. Seeing how comfortable and relaxed Nina is with her means everything to me. She has earned my complete trust, and she will always be my first choice whenever I need someone to care for Nina. I recommend her with all my heart. Thank you for taking such amazing care of my little girl!”
“Christiana and her family took excellent care of Nola while we were away. She sent daily pics & updates which made us feel at ease that Nola was being well taken care of and enjoying her stay. We will definitely have Nola stay again! ❤️”
About: I welcome your fur babies to play with our own dogs in our home and fenced in backyard for plenty of room for playtime. A lot of doggie play dates with neighbors dogs too. Have experience with young and senior pets of our own. I foster dogs as well with Rescue Gang and after adopted honored to have several come back here for us to babysit. So much love be to shared and our own dogs are very welcoming! I work from home and ready to spoil your dogs. Pretty open schedule to help accommodate your needs at our loving, playful home. Lots of potty breaks for your fur babies and playtime. I have a fenced in yard and can run around and play with our own dogs who are very friendly. They will get lots of cuddles and welcome anywhere in our home. Can’t wait to spoil your doggie like we do for our own!
“David is a wonderful dog sitter for Willow. When I drop her off it's like dropping her off at her best friend's home. She walks around and checks out the front yard and the garage and happily goes in the house with David. Breakfast and walks down the road with David and she's in love forever. David is so accomodating and cares so much for Willow, I have no reservations leaving her in David's trusting care.”
“One word: AMAZING! Updates and photos multiple times a day and incredible response time. This was the first time leaving my two dogs with anyone away from home and after working with Angie I would not hesitate to have them stay with her again. There was never a worry or a concern. Thank you, Angie!”
“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!”
“Jennifer was very friendly and receptive to everything. I had to tell her about Kona. She kept me updated with pictures and let me feel confident that she was well taken care of They had two dogs that were very friendly with Kona.”
“I had the pleasure of having Nikki and her lovely family watch our dog, Kota, who has a history of seizures and requires a little extra care. She did a truly wonderful job. Throughout Kota’s stay, she sent frequent pictures and updates, which helped ease our minds and kept us informed. Her attentiveness, kindness, and clear communication were greatly appreciated. Kota was in excellent hands, and it was clear she treated her like one of her own. I would highly recommend her to anyone looking for dependable, compassionate care for their pet—especially if they have special medical needs.”
About: I’ve been surrounded by dogs all my life. I grew up showing dogs, both my family dogs and others. My family back home currently has three dogs, each a different size, from small to large, so I have experience with all sizes. I live in a great area for casual walks, with a dog park and a small lake nearby for the pups that are allowed to swim! I work full-time, in-office Monday through Thursday and from home on Fridays. I take daily walks around my neighborhood in the evening. On weekends, I love exploring a new coffee shop and walking trail or just a longer walk in the areas near me. I’d love to bring your pet along with me on walks and for downtime on the couch afterwards! I don’t have a fenced yard, but there is a dog park where your pup can run freely. Outside of that, we have open grass areas where we can walk. All pups are welcome on furniture at my place and are welcome to enjoy the space as their own. I do have a patio that they’re more than welcome to sit outside and enjoy with me.
“Ashlee was very communicate and sweet during Frankie’s stay with her! She was flexible and followed all of our requests. She sent updates with photos each night. Thanks Ashlee!”
“Michelle was great with our two pups! We have tow energetic labs and they felt right at home with her. Got updates daily on how they were doing. Would definitely book with her again!”
“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!”
The median cost per night for dog boarding in Oconomowoc is $45
Dog parents share their Rover experiences - Oconomowoc
Our little guy received excellent care with Brooke and her husband. We loved the updates, pics and videos. It really reassured us as it was his first visit there. He had an another Frenchie to play with so that was awesome! Very grateful for their care and making him feel comfortable, safe, and welcomed in their home.
We had an excellent experience with Natalie caring for Nala while we were on vacation. She kept us informed with regular updates, and it was clear that Nala was happy and well cared for. Natalie treated Nala like her own, and we highly recommend her to anyone in need of a reliable and compassionate dog sitter.
Jack and Jennifer are great sitters. You can expect your pets to be well cared for. My 2 boys came home happy. If you have any questions, you will get a quick response. Jack and Jennifer also send pics to see the fun your pups are having while you are away. I highly recommend them as sitters.
Our dog usually stays with family if we leave but it wasn't an option this time. We went on our honeymoon and trusted Courtney with our dog Deku. She kept us extremely updated on everything, sending pictures of him. We couldn't of asked for a better communicator, especially with a part of our family. Would highly recommend using her services, and will return if we ever need them again. Thank you again for everything.
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 - Oconomowoc
Select a filter and find qualifying sitters offering dog boarding.Sitters in Oconomowoc average 12 repeat dog boarding clients
FAQs for Dog Boarding - Oconomowoc
Frequently asked questions about Rover
The average cost of Dog Boarding in Oconomowoc is $47 per night as of October 2026. Most bookings cost between $30 and $64 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 October 2026, there are 802 sitters on Rover offering Dog Boarding across Oconomowoc. Enter your ZIP code to see which available sitters are closest to your home.
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 Oconomowoc 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 Oconomowoc home-away-from-home, 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 Oconomowoc.
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 Oconomowoc 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 , 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 .
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.
Connect anywhere with the Rover app
