Dog Sitting Windsor
Book a Windsor dog sitter to watch your dog in your sitter’s home or yours.
Over 104 pet parents in Windsor have booked dog sitting
Windsor, Find top rated dog sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“We were so fortunate to have Lisa take care of our German Shepherd while we were out of town one day over the Memorial Day weekend. Lisa came to our house ahead of time for a meet/greet, and it was clear she was a dog lover and would take great care of our pup. During her drop in visits, she not only fed our dog, but also administered medication, took him out to play fetch (his favorite game), and spent time cuddling/petting him. We would recommend Lisa to any pet owner and will definitely ask her to watch our pup again! Thank you Lisa!”
About: Although I have not been a trainer, I have raised my own puppy, as well as been around dogs my whole life! I love nothing more than dogs and the joy they bring to peoples lives, I know times can get busy, but that’s what i’m here for! I have my own puppy at home, and i love spending time with him, but i also love spending time with other dogs:) i love going on walks, and to parks around the neighborhood! I will make sure your pet is actively cared for while I am with them, I will play with, and attend to their special needs!
“Lexy is a true dog lover. Nina warmed up to her right away. We felt totally comfortable having Lexy stop in for a drop in visit. She kept us update on her visit. Looking forward to using Lexy again to take care of Nina.”
“We had a great experience with Abigail taking care of our two senior dogs over Memorial Day weekend! She was communicative, prompt, and consistently checked in when questions came up. We really appreciated her flexibility and willingness to accommodate our dogs’ individual needs and quirks. It gave us peace of mind knowing they were in reliable and attentive hands while we were away. We’d absolutely book with her again!”
About: I'm the person asking if I can pet your animals in public. Love a good walk and will play outside with your pet or snuggle on THe couch if desired,! My workday usually starts at about 9am and I am home sometime between 3-4pm My weekends are usually wide open for your pet care needs Pets can roam free in my home as long as behaved and appropriate. I feed my cats twice daily so I can accommodate feeding routines and have a fenced in yard for play
About: I’ve taken care of all kinds of dogs! Small or Big not a worry! I love being outside on a long walk but also don’t mind snuggling on the couch if needed!:) I do work a full time job but it’s quite flexible with being able to leave for them to be let out quick if needed! I’m free most days after 4pm and don’t start until 9am most days! I’m the kind of person to act like your dog is my dog! Only the best for your pets because I get it you want the best for them!:) I love to play and give scratches but I’m also willing to cuddle like I said !
“Rebecca was absolutely amazing! Very sweet and attentive to my cat and her needs, and she sent pictures and detailed updates with how my cat was doing at each visit. So appreciative of her!”
About: I have always had a strong passion for working with animals. I have 5 pets of my own and currently work at a vet clinic which provides me with additional resources . I know how to feed, clean up after, and medicate animals. I have worked with all sizes and ages of dogs and cats. I have experience with all kinds of breeds and animals with different physical and nutritional needs. I I work part time at a vet clinic and coaching on the weekends. Monday- Thursday I am able to be home in the morning and night with a possible stop by in the afternoon to let animals out or check in on them. On the weekends I am there in the morning and home either mid afternoon or in the evening to check on animals and be there for the night. I keep them calm and comfortable by being in their own home. Keep them on their normal routine so they won't feel more uncomfortable without their owners home. I make sure they get plenty of exercise, attention and love, and make sure they get any meditation they need. I keep the house tidy and clean up any messes made by the animal while there.
About: Dogs have been part of my life for as long as I can remember! I grew up with multiple family dogs, mostly larger breeds. After college, I adopted a dog of my own who was by my side for 10 wonderful years. I've also spent the past decade volunteering at local animal shelters, which has given me hands-on experience with dogs of every size and temperament, from tiny pups to gentle giants. Along the way, I've learned how to work with nervous or anxious dogs, administer medication, and care for the specific needs of senior dogs. Whatever your dog needs, chances are I've handled something similar. I can't wait to meet your pup and give them all the love they deserve! My schedule is very flexible, which makes it easy for me to work pet care into my day. My day job is fully remote, so I'm able to build walks and drop-in visits around my work rather than being tied to a rigid 9-to-5. Right now I have even more flexibility, since I'm between roles, so I can typically accommodate last-minute requests or visits at times that might be trickier for others to fit in. Since I offer drop-in visits, walks, and house sitting, I spend most of my time in your home rather than mine — so keeping things safe and familiar for your pet is my main focus. - I go over feeding, medication, and routine details with you before I start, so nothing gets missed - I double-check leashes, harnesses, and collars before every walk - I lock up and secure the house every time I come and go - I'm comfortable with nervous or anxious dogs — I read their body language and never rush them - I can manage medication schedules and give senior dogs the extra care they need - I send photo and video updates so you always know how your pup is doing - I keep your vet's info on hand just in case Your home, your routine, your dog — I just fold right in and keep things running smoothly while you're away.
About: I have taken care of large Akitas my whole life. They were very difficult to walk and struggle with other dogs so plenty of experience with more difficult walkers. I also currently live with a Jack Russell! Recent UVA Law graduate waiting for my job to start in January so available almost any time of day. Need more of a heads up for last minute walks to make sure I can be there, but other than that I am a trustworthy young adult with a lot of time on her hands! Handle everything I do with extreme care. I will make sure to treat your pet with the upmost care and concern necessary for any walk or check-in.
About: I've had 2 family dogs and 4 cats! As well as helping take care of friends and roommates pets. I love them and it's fun for me, just thought it'd be a cute and easy way to make a little extra money. I work full time so can only do quicker drop-ins in the mornings and/or evenings during the week but could drop by more over weekends! Am good to drop by homes/apartments and feed/walk/hang out with pets for a bit, not available to care for them from my apartment.
“She was sooo amazing!! Could not have asked for a better sitter and peace of mind. Updates and pics and communication was great. Will definitely be using her again if she's willing and available.”
“Great communication, wonderful care of our 2 cats while we were out of town. Sidney even picked up some extra food because I had miscounted the number of cans we needed. Thanks so much!”
“Emily was wonderful watching our dog for a few days while we were out of town. She was prompt, great with communicating, and very trustworthy. I felt very comfortable knowing our dog was being well cared for. I would highly recommend Emily to anyone and would absolutely book with her again! Thank you Emily!”
About: I am currently a full-time Team Coordinator that works remotely out of my home, or any place with wifi! Working remotely has provided me with a lot of spare time, not having to commute to and from work, so I am looking to fill some of that time caring for animals. I currently have two dogs and two cats at home. I have experience with all types of dogs including small dogs, like my dad's Peekapoo, and large dogs, like my brother's Great Dane. I've taken care of puppies as well as senior dogs with extra care needed included insulin injections and eye drops. I am available for entire weekends, individual weekend days, full weeks and individual week days. I look forward to meeting you and your pet(s) and please don't hesitate to ask me any questions! If weekdays are needed, I have the flexibility to work from your home which gives me the opportunity to be there all day long if needed. Only working from 7:30am to 4:00pm with no commute gives me plenty of extra hours for pet/house care. I will treat your pets and home with the utmost respect as if they were my own. I would ask for any special requirements that pertain to housesitting and pet sitting ahead of time so I can follow them when I am there. I always make sure to lock doors and stay vigilant, especially at other peoples’ homes. I can be available to you by phone any time of the day or night when I am watching your pet/house and am always willing to help out with anything that may come up!
About: I grew up with dogs, cats, and horses, and have experience in oral med administration with both cats and dogs. I have a soft spot for the big dogs (they're lap-sized if you commit!). I run half marathons so getting good exercise in will be no problem (even in Wisconsin weather!). I'm currently training for distance running, so you can expect great exercise for your pet! Whether it's a long meandering sniff-ari or an intense loop around the neighborhood, I would love to know what fits your dog best. As I'm in your home, your instructions are paramount. You know your pet better than anyone, and I am happy to keep their normal routines in place. I like getting to know each animal and their unique personality, and while I *love* giving snuggles and pets, I understand some pets prefer their space.
About: I am a loving, compassionate, and reliable person that has a love for animals. I am also athletic and can take your puppy companion for a jog! I have unlimited availability for pet care. The only time I am not available is at 3pm, when I pick up my two pet loving children from school. I have a fenced in yard in a nice neighborhood, and a lake across the street if your pet likes to swim. I am also available to come to your home as well. I am available in Rock County and Dane County.
The median cost per visit for dog sitting in Windsor is $20
Dog parents share their Rover experiences - Windsor
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 sitting
1. Search
Browse profiles of sitters near you who offer dog sitting.
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 sitting - Windsor
Select a filter and find qualifying sitters offering dog sitting.Sitters in Windsor average 7 repeat dog sitting clients
FAQs for Dog Sitting - Windsor
Frequently asked questions about Rover
The average cost of Dog Sitting in Windsor is $19 per visit as of October 2026. Most bookings cost between $11 and $27 per visit. 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 1,373 sitters on Rover offering Dog Sitting across Windsor. Enter your ZIP code to see which available sitters are closest to your home.
You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.
Before booking, confirm:
- the timing, length, and frequency of visits;
- the care instructions the sitter should follow;
- which parts of your pet’s usual routine should be prioritized;
- how often you would like to receive messages, photos, or other updates.
Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Windsor choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
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 .
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.
A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet or the new environment.
During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .
While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.
To find sitters in Windsor with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.
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
- 93% can help with giving oral medications or injections
- 94% 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.
sitters on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
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