Dog Boarding Windsor
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 121 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.
“We just completed our dogs 3rd stay at Sarah and Zach's house and we already have stay #4 booked. Our always have so much fun and get lots of outdoor playtime. We love the photo and video updates and especially enjoy knowing they are being so well cared for while we are away.”
![Sitter Profile Image: LAVAL [VAL] S.](https://www.rover.com/cf-image-cdn/remote/images/people/3gmOZo1A/czdjwirazm/original?width=200&height=200&quality=70&fit=cover)
“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.”
“Shawn was great! Sent picture updates and Caspian looked so happy and relaxed! He was super flexible and even worked with me as I needed to have a friend pick Cas for scheduling reasons. Thank you Shawn!”
“Brandon and Katy are lovely! They were very helpful moving my dog's crate and getting him settled. Sammy had a great time playing and cuddling.”
“Michelle and her family cared for Chuck as if he was their own. As a dog that struggles with separation anxiety, I worry about going away, but the pictures and updates about Chuck showed him to be comfortable and relaxed. Michelle was easy to work with and clearly an animal lover.”
“Toni was amazing! This was our first time leaving our puppy with a sitter and we were so impressed! Annie clearly had a ton of fun, she came back absolutely pooped! Toni also sent us lots of updates and pictures :)”
“Ellen took terrific care of our old girl! She went above and beyond helping her get through a few health/diet issues that came up during the stay. Very responsive and helpful updates throughout the stay. Would recommend Ellen to anyone looking to board!”
“I would recommend Ndaziona to anyone who wants a great dog setter. Nikita was given best care anyone could ask for. During the time that she was with this family we continually got updates and pictures setting our mind at ease, knowing she was getting the best care we could have asked for. Again I would highly recommend this setter.”
“Allison went above and beyond! She treated my dog like she was her own, and I felt completely at ease while I was away. I’m definitely pretty particular about who I trust with my dog, and I had absolutely no hesitations with Allison. She was so caring and loved sending all the pictures (which I obviously LOVED ). It was clear my pup was having the best time and was so well cared for. I would 100% have Allison watch her again and would highly recommend her to anyone looking for a sitter!”
About: As a pet owner myself, I understand how important it is to trust the person caring for your fur babies. I currently have my sweet girl Nova at home and am comfortable with pets of different temperaments and needs. I strive to create a safe, stress free experience while keeping owners updated with lots of photos and messages. Whether your pet needs playtime, cuddles, medication, or just a consistent routine, I’ll make sure they receive attentive care. I’m currently a SAHM with a very flexible schedule, allowing me to provide reliable care and accommodate a variety of pet care needs throughout the day. Your pets are treated like family! I have 1 cat in my home currently that is okay with dogs that visit. I maintain a clean, safe, and pet-friendly environment and carefully supervise interactions at all times.
“Cleda was awesome! She took care of our dog as well as we would have ourselves. Frequent updates, communication, and feedback; and a really great environment are just some of the great points.”
“Tessa has been an absolute delight and I'm so glad to have trusted her with my Trixie. She helped celebrate Trixie's birthday and took her on so many walks and ample outside time! Highly recommend Tessa (and Tennessee)!”
“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!”
“Kara is one of a kind! My dog Tashi spent nine days with Kara at her home with her animals and was cared for as one of her own. We got an update every single day about how she was doing and pictures which reassured us since we were nervous about being so far away from her for such an extended time. Tashi got to hang out with her dogs in her backyard, got her daily walks, got lots of couch and bed time, and was super well looked after and cared for. We are so grateful to have found Kara and know that we can leave and Tashi will be happy and in a home where she feels so comfortable and is in such good hands. Kara even allowed us to pickup at 10:45 pm after a late night flight home! Thanks a million!”
About: I’ve been an animal lover and care taker as long as I can remember. I grew up in the country and was always finding stray animals that needed nursed back to health. I have a very flexible schedule right now. Can do any time of day, any day of the week. I am extremely active and love playing and walking with animals. I will follow instructions to a tee no matter how specific. There will never be judgment. I will remain extremely cautious and present in my interactions.
The median cost per night for dog boarding in Windsor is $45
Dog parents share their Rover experiences - Windsor
Kris and her family took such amazing care of our pup! She was incredibly flexible with timing and even met up with us beforehand so she could get to know him. While we were away, she sent us tons of pictures, videos, and updates, which gave us so much peace of mind. We could tell he was happy and well cared for the whole time. We would 10000% recommend Kris and her family! ❤️
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.
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 - Windsor
Select a filter and find qualifying sitters offering dog boarding.Sitters in Windsor average 11 repeat dog boarding clients
FAQs for Dog Boarding - Windsor
Frequently asked questions about Rover
The average cost of Dog Boarding in Windsor is $28 per night as of November 2026. Most bookings cost between $27 and $61 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 442 sitters on Rover offering Dog Boarding across Windsor. 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 Windsor 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 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.
Yes, you can find sitters who have experience with handling special pet needs in Windsor. On Rover:
- 89% of sitters can help with special care needs
- 96% 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 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.
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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