Dog Boarding Windsor
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 392 pet parents in Windsor have booked dog boarding
Windsor, 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.
“Finny had a blast! I got updates every day and I could see how happy and content he was while I was on vacation. I was very comfortable knowing he was safe and having a great time, and when he got home he was good and tired. Thank you so much! I would be super happy to bring him back and would highly recommend.”
“Edith sent many photos and kept me informed from the moment Ollie was dropped off until I picked him up. He was well taken care of and I would definitely ask her to watch him again.”
“Paula was great communicating and even ended up spending the evenings with my pup on the sofa since she wasn't comfortable alone. She also gave necessary medication and kept track of everything as I had asked. She sent pictures and kept my dog happy and safe, would recommend and use again. Thank you!”
“I can't recommend Stephanie highly enough! She recently watched our dog, Hazel, and she was truly wonderful from start to finish. From the moment we dropped Hazel off, Stephanie provided excellent and frequent updates, including photos and videos, which really put our minds at ease. It was clear that Hazel was having a great time and felt completely comfortable in her care. Stephanie was incredibly reliable, easy to communicate with, and genuinely treated Hazel like her own family. Hazel came home tired, happy, and clearly well-loved. If you're looking for a trustworthy, loving, and professional sitter on Rover, book Stephanie—we certainly will be booking her again!”
“Ronalisa was amazing with Pepper. She would be great in hosting any dog, and for sure she is skilled at hosting an elderly dog. This one... originally a rescue who may well have been abused, now ~14 years old, deaf, extremely anxious to be left alone, and suspicious of new people... could have been a challenge. Rona took it all in stride, easily handling the regime of medications and food preferences and totally winning Pepper's heart.”
“Fabulous! Mack gave her 4 paws up and he would have given her more but he only has 4 paws. He has been online trying one to buy me more airline trips so he can go back to Steph and live the good life. Can’t praise her enough. Deb Spencley”
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“He’s amazing with my dog. He understands how she’s upset with changes and is patient with her. My dog seems to enjoy her time with him and is happy and healthy when I pick her up.”
“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.”
“Jessica and her kiddos were great to my dog! He got along well with her doggos and she kept them all super active! Really appreciated all the pictures and updates while I was gone. Would 100%book with her again!”
“Emily and her family were great. She gave our dogs lots of love, interaction and exercise. She made our dogs feel like they were part of Emily’s family. Also really appreciated daily notes and photos. We will have Emily and her family take care of our dogs again!”
“Amazing people who love and care for my pup while he is with them - they also send the cutest pictures and updates! They were also super understanding when I got stuck in traffic on the way to pick my dog up.”
“Margaret was beyond sweet and accommodating, she took excellent care of my senior pup and gave her plenty of attention, care, and exceptional feedback. We’re new to the area and will only book with her, she's earned a trusted client. Highly recommend Margaret for any pet sitting needs!”
“Lindsay took great care of my dog, Taydo. Long walks, snoozes on her couch, and photos to keep me updated. I believe LIndsay to be completely trustworthy which is really important for a pet sitter.”
“Mary and her family were absolutely wonderful sitters for Grizzy! They took great care of him during a cold snap, making sure he was warm and comfortable. Mary sent wonderful updates and absolutely adorable pictures, and I would recommend her to anyone!”
“Duane and Lauren are always so accommodating and flexible when we book with them! Our pup is always exciting to stay with them and it makes me happy to know she likes to be there! Thank you so much Duane and Lauren for always taking care of Stormi!”
“Bentley had a great time with you both! Thanks for taking such good care of our baby! We REALLY appreciated the pictures you sent while he was with you, too! We will absolutely book with you again.”
The median cost per night for dog boarding in Windsor is $45
Dog parents share their Rover experiences - Windsor
This was our first boarding experience with Morgan and she was awesome. Our dog is a bit anxious and slow to warm up to people. It was clear from the start that Morgan understands dogs and can match their energy. She took great care of our Rosie and sent regular updates. It was great to enjoy our vacation without worrying about the dog. We also had some flight issues on the way home and Morgan was flexible and helpful.
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 for dog boarding - Windsor
Select a filter and find qualifying sitters offering dog boarding.Sitters in Windsor average 11 repeat dog boarding clients
FAQs for Boarding - Windsor
Frequently asked questions about Rover
The average cost for Dog Boarding in Windsor on Rover is $36.63 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 444 sitters on Rover offering Dog Boarding across Windsor. 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.
89% of Windsor 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 Windsor 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 Windsor 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 Windsor.
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 Windsor 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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