Dog Boarding Oconomowoc
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 291 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.
“We are return customers and we are so thrilled with the care Homer gets at Anna's. He is treated like one of the family and absolutely loves it there. Our family has no hesitation leaving Homer with Ana because we know he will be getting the best possible care while we are away. ”
“Jenifer was amazing!!! My dog was so happy at her house And I could relax leaving her there!!! She sent pictures which was so fun and such a plus and answered any texts I sent very promptly!! I can’t wait to use her again!!!! THANK YOU!!❤️”
“Heather is a fabulous dog sitter! We boarded our pup, Ivy, at her home. We had to extend Ivy’s stay by one night and Heather was extremely accommodating. Ivy even went on a few outings with her! When we dropped our pup her home, I could tell upon meeting her that Heather’s demeanor is gentle and calming.”
“Scott & Ashley were amazing with communication & updates putting this worried heart at ease. Fred was very well loved and we would definitely have him stay there again.”
“Remi did very well staying with Marie and her family. She was wonderful with him! She took him for walks and he also got lots of play time. She updated us often while we were gone as to how he was doing and also sent lots of pics. We will definitely use her as a sitter again!”
“Went great! This was a last minute booking when we needed to get away for the weekend. I never met Brooke, but her husband got down low when he greeted my dog, and my dog Blue immediately "kissed" him. That was unusually fast! Must have felt super comfortable with him because he went right into the house and never looked back at me. I was given pics and videos each day and felt comfortable with him being there.”
“Jack and Jenni are absolutely wonderful with Leo. They take such good care of him - Always attentive, taking him on walks, and making sure he's happy. they also send videos and photos, which gives peace of mind and a lot of confidence. I truly feel that Leo is in great hands every time. I highly recommend them.”
“Ruby was great with my dog! He was able to go with her wherever she went and had a bunch of new experiences. Ruby was very accomodating and returned him happy, clean, and tired.”
“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”
“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!”
“Tracy was great with Hana and gave frequent updates and pictures. Tracy clearly has great experience taking care of dogs with all types of temperaments and I felt Hana was in great hands!”
“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!!”
“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!”
“Maria watched our two golden doodles while we were on vacation for a week. This is the second time we’ve used her and she’s always been great. She sends updates with photos/videos multiple times a day. I can tell our boys were well taken care of. Would definitely recommend.”
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.
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
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3. Book & Pay
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Popular requests for dog boarding - Oconomowoc
Select a filter and find qualifying sitters offering dog boarding.Sitters in Oconomowoc average 11 repeat dog boarding clients
FAQs for Boarding - Oconomowoc
Frequently asked questions about Rover
The average cost for Dog Boarding in Oconomowoc on Rover is $44.4 per night (as of August 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 August 2026, there are 818 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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