Dog Boarding Oconomowoc
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 279 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.
“Katy and DJ are wonderful sitters! We are so at peace leaving our dog Milo in their care. They send us frequent updates and pictures. Milo is worn out by the time he comes home. He loves his walks and playing with their pup! I would highly recommend them!”
“Scott and Ashley (and kids!) were amazing. We'd never boarded our two dogs anywhere so we were quite nervous about leaving them, but they kept us updated with regular photos and responded quickly to any message. The dogs got regular playtime and lots of snuggles and clearly became part of the family. We could not have been happier with this experience! I cannot recommend them highly enough. Thank you!!!”
“Jenifer took great care of Hazelnut while we were on vacation. Hazelnut is a little shy but took to Jenifer right away. Jenifer is very responsive and sent us lots of cute pictures while we were away. A+”
“Heather was communicative and very accommodating, even making the time to pick up our Teddy from our wedding venue after his role in the wedding. Teddy had a great time and was so happy to stay with her!”
“Madison and Jeff were very easy to communicate with and kept us advised of all of Roscoe’s activities with texts and pictures . Their boys were very good playmates and kept Roscoe very busy. At night the boys setup “camp” in the living room and slept with Roscoe. Awesome Family!”
“Our puppy had a great first time with Doreen. She sent daily updates and photos to keep us up to date with how he was doing. We felt very comfortable leaving our puppy with Doreen for the weekend”
“Brooke was amazing! Super loving and kind to our pups. We booked her last minute and she was able to accommodate with open arms. She sent photos of her and her boyfriend playing with them and cuddling them. I highly recommend Brooke! She’s a gem ❤️”
“An excellent experience! As a first-timer with Rover we did not know what to expect. Marie made the experience smooth and put us at ease. Bam had a great time & received excellent care. We received many updates & pictures.”
“My dog had the BEST weekend away from me!! Dropping my dog at Dana's was like dropping him at the Ritz! Dana was so gracious, welcoming and accommodating- making sure she knew my dog's preferences and comforts. Her two pugs were adorable and Sammy seemed to enjoy having them as playmates! I loved all the pictures and updates. My sporting dog can be a handful but Dana seemed to manage his care with ease and kindness. Her backyard & deck is beautiful. She is a gem of a dog lover! I reside in Illinois. I needed her services while traveling...I may need to pay her to "relocate" ha-ha. Thank you, Dana. My dog transitioned home beautifully. You're the Best!”
“Great communication from initial contact until pick up. Appreciated the daily updates and pictures. Biscuit had a great "staycation" over the weekend. We will use Anna for our dog sitting needs again.”
“This was our first time using Rover and we didn't know quite what to expect. We set up a meet and greet to make sure it would be a good fit. As soon as my dog got out of the car, I could tell she was going to like it there. Alex was very communicative during the whole stay and sent daily pictures of how my dog was doing. This made us very happy to know she was in good hands while we were gone. We will definitely work with Alex again!”
“It was just an overnight visit but the puppies are still exhausted! They’re must’ve had a great time 🥰. Cheryl kept in touch with verifying meds and letting me know they we’re doing great🥰🥰🥰thank you again!”
“Joanne was a LIFE SAVIOR ! I had a last minute cancellation and she responded right away and was able to help take care of Atlas. She was super communicative, shared great photos, and took amazing care of Atlas incredibly impromptu! Thank you thank you thank you !”
“Gianina was a great host to Kona! She sent pictures and updates throughout the weekend! She had a great yard for him to explore, and she took him on nice walks. We will definitely book with her again if we travel!”
The median cost per night for dog boarding in Oconomowoc is $45
Dog parents share their Rover experiences - Oconomowoc
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.
We had a good experience with Natalie during our dog's stay. She has a very large fenced yard that allowed our high energy pup to get her zoomies out regularly. She seemed very detail oriented, and took notes when we discussed various things about our dog's care prior to her drop off. We would certainly book again with Natalie!
Our dog Phoebe had an absolute blast during her stay here. She loved playing with Moxie, their dog. She was super happy and tired out when we picked her up. Usually, Phoebe has a bit of anxiety when she's somewhere new, but she warmed up so quickly to Brooke, Robbie, and Moxie. We will definitely be booking with them again. It gave us such peace of mind to know Phoebe was well cared for and loved while we were gone.
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.
Meet local sitters who will treat your dogs like family
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 near you
Select a filter and find qualifying Oconomowoc sitters!Sitters in Oconomowoc average 11 repeat dog boarding clients
FAQs for Dog Boarding - Oconomowoc
Frequently asked questions about Rover
The average cost for Dog Boarding in Oconomowoc on Rover is $44.4 per night (as of July 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 July 2026, there are 826 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 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.
87% of Oconomowoc 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 Oconomowoc 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 Oconomowoc 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 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 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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