Dog Sitting in Windsor
Book a Windsor dog sitter to watch your dog in your sitter’s home or yours.

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Top rated Windsor dog sitters
“This was the first time I booked Le'Andra to do daily check-ins on my cat Gabby while I was out of town. She was great! Le'Andra always stayed in communication with me by text. And she did her best to still take care of my cat while also dealing with the storm and very cold temperatures we recently had. Le'Andra is nice and very friendly. I would definitely request her again the next time I need a cat sitter, and would also recommend her to anyone considering booking her on Rover.”

“Andrea is great! She communicated throughout the entire process. She kept me informed on how everything was going. She sent pictures showing her interaction with Snuggles. Although, she wasn’t booked to care for the cat, she notified me of his mischievous behavior. I will definitely book with Andrea again. Thank you Andrea!”

About: I have taken care of animals for 15 years and I am very passionate about making animals feel safe, comfortable and loved. I grew up with both cats and dogs and so I am able to take care of both. From pugs, mastiffs, labradors, to cats, I can do it all. I give medication, deep-clean litter boxes, play with you pets and overall make sure your pet feels at ease while you’re away. I am currently a full time employee that works nights (5p-2a), and so I have a lot of free time during the day to take care of your pet. I always get up early to make sure I’m taking care of me and my cat’s needs and am able to extend that care to your animals as well. When I do a drop-in visit, I always do a sweep around the main areas of the house to ensure that everything is in order. For dogs, my main priority is to take them out, check their water bowl and play with them to make sure they have the care they need for the day. For cats, I will always check their litter boxes to see if it needs any scooping, I will also check their food and water bowls and fill them up if needed. Like dogs, I will respect their boundaries and play with them to ensure they’re comfortable.

About: I’ve had dogs of my own my whole life and taken care of neighbors pets as well. I’ve done drop in visits and walks for neighbors dogs and cats while they were away. I currently have a dog of my own named Leo he’s a super sweet boxer lab mix who’s great with all animals and people. This summer I am free a lot and can make my schedule work around any drop ins and walks. I just need a day or two notice so I can plan around everything but I look forward to working with your pets. I love animals especially dogs. I’ve always been very kind to animals making sure they feel safe with me and know I want to care for them. I like to make sure dogs understand me and that can create some trust and build a good relationship.
About: My career training makes me hyper aware of my clients needs whether they be human or animal. I can meet them where they are physically and mentally and cater to their needs. My work is flexible so my schedule can fit your pet's routine. I typically do my workout in the early morning which leaves the remainder of the dedicated to your pet's priorities. When I'm with your pet/s they are my priority whether it's feeding, walking, playing or just cuddling. I love animals but can't have them because of my husband's health issues. Yours is the best I can do.
“I am extremely happy with Joanna! My dog, Loki had a fantastic time and he was just as happy as he usually is, I could totally tell by the pictures she sent me all the time. I am very grateful for the time she spent with him and how well she took care of him. I will definitely have her stay with him again in the future.”

“Tara was excellent. She was prompt and prepared to start right in, We found her energetic, kind, thoughtful and most thorough. She immediately engaged our trust and confidence. Our dog was totally smitten. Tara was just like family. I recommend Tara most highly. She is a delight to work with.”

“Karinna is awesome! She did an excellent job looking after my cat on short notice, and I'm looking forward to being able to use her services again. Thank You Karinna!”

“Laura provided such great care for our pets (two pups and a cat). She was kind, loving, and really engaged with them (petting, playing fetch, etc.). I highly recommend her and will definitely be utilizing her services again!!!”

About: Nice to meet you. My name is Amy. I am a high school Spanish teacher on summer vacation, and I am available every Tuesday, Wednesday, and Thursday this summer to walk your dog or check in on your pets while you are away. I have experience with cats, dogs, horses, and chickens. Yo hablo español (et un peux de français!) I am available mornings and afternoons on Tuesday, Wednesday, and Thursday throughout the summer, from late June to mid August. Check my schedule on Rover to see my availability ! I am happy to feed and brush your pet; play with them; take them for walks. I can administer medication, clean up messes. If you have a cat, I can also feed them, brush them, and clean their litter box.

About: I had a maltese puppy for 10 years from age 9 weeks onward and most recently had a shih tzu puppy that turned 1 on 5/28/25. In the oast I've had pets including hamsters, guinea pigs, chickens, and fish of my own. I work from home and have a flexible schedule, so your pup will get lots of attention and care throughout the day. Here's what a typical day looks like when your dog is with me: 🐾 Morning (7am–10am): Potty break, breakfast, and a light walk or play session 🐾 Midday (11am–2pm): Walks, potty breaks, enrichment games, or just relaxing cuddle time 🐾 Afternoon (3pm–6pm): Another walk or active playtime in a safe, calm environment 🐾 Evening (7pm–9pm): Dinner, a final potty break, and winding down for the night I'm available for: ✅ Drop-in visits ✅ Dog walking ✅ Puppy care Weekend and holiday availability included! I’m happy to accommodate special routines, medications, or specific instructions your dog needs to feel comfortable and loved. When you trust me to care for your dog, I show up with love, respect, and attention to detail — all in the comfort of your dog’s familiar surroundings. 🐶 In-Home Peace of Mind: I care for pets in their own homes, where they feel most secure. Whether I’m dropping in for a quick visit, taking your pup for a walk, or staying overnight, I follow your routine closely to minimize stress and keep your dog calm and happy. 🦴 Personalized, Gentle Care: I specialize in small breeds and have over 10 years of experience. From meal schedules and potty routines to medication or calming techniques, I provide care tailored to your dog’s specific needs. 🚶🏽♀️ Safe & Engaging Walks: Walks are done one-on-one in familiar areas, with close attention to your pet’s energy level, leash behavior, and comfort. I avoid crowded dog parks or risky environments to keep your dog safe. 📝 Trustworthy & Transparent: I communicate clearly, provide updates, and send photos during every visit. You’ll always know how your pet is doing, whether I’m there for 20 minutes or staying the night. Your pet stays safe, your home is respected, and you can relax knowing your furry family member is in loving, responsible hands.
“This is the 2nd time we’ve booked Alex to care for our 2 kitties. She is very friendly and reliable. She commented daily with us sending pictures each time each time. We will definitely use her again!”

About: At home I've been taking care of Ramsey, my small, high-energy, dog for almost 9 years. In these 9 years I've gained a larger a sense of responsibility and my love for animals has grown tremendously. I know how to communicate with dogs and read dog body language in order to cater to their needs and give them best care. As a recent graduate, I have more flexibility in my schedule, I can dedicate ample time to caring for my pets. This includes feeding, grooming, walking, and spending quality time with them to ensure their well-being and happiness. Engaging in activities like playing, training, and companionship not only enriches their lives but also brings a sense of purpose to my day. While job hunting, I find solace and a sense of responsibility in taking care of my pets, creating a positive and fulfilling routine amidst my current situation. At home I make sure my dog cannot access anything that can harm him. I close doors to the bathroom so he can’t access the trash can and I put gates up around the house to areas he can’t be in. During walks I am very careful and aware of my surroundings. If I walk at night, I walk in a well lit area with a few friends.
“Arianna was absolutely amazing with our pup Oakley. She gives the confidence to be able to handle any situation that may come up. Highly recommend, and will be using her services again!!”
Over 18 pet parents in Windsor have booked dog sitting
Windsor dog parents share their Rover experiences
I had an excellent experience with Jalah and couldn’t be happier with the care they provided. From the very beginning, she was punctual and arrived exactly at the scheduled time, which immediately gave me confidence and peace of mind. Jalah followed all of my instructions carefully and paid close attention to the details of my pet’s routine, which I truly appreciated. It’s clear she takes her responsibility seriously and genuinely care about the animals she look after. What stood out the most was their communication.Jalah kept me consistently updated, especially during my pet’s transition to being with someone new in my home. Those updates made a huge difference and reassured me that everything was going smoothly. Overall, I highly recommend Jalah to anyone looking for someone reliable, attentive, and communicative. I would absolutely trust her again in the future!

Popular requests near you
Select a filter and find qualifying Windsor sitters!How Rover works

1. Search
Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for dog sitting in Windsor is $21
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 dog sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Windsor average 5 repeat dog sitting clients
Dog Sitting FAQs
Frequently asked questions about Rover
Dog sitters on Rover are free to set their rates. The median cost to hire a dog sitter in Windsor on Rover as of Jun 2026 was about $21 per night, after factoring in Rover’s service fees. A dog sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.
As of Jun 2026, there are 2,258 dog sitters in Windsor. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, 87% of Windsor dog sitters respond in under an hour.
Dog sitters in Windsor have an average of 17 years of experience. Dog sitters with repeat customers have an average of 5 repeat clients. Experience can vary from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Windsor.
Rover makes it easy to find Windsor dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:
- Dogs of all ages and abilities, including puppies
- Dog parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their dog sitter’s pets
There are 2,258 dog sitters in Windsor on Rover, so you’re sure to find the perfect match for your dog! In Windsor, 98% of dog sitters offer daily exercise, 96% offer medication administration, and 95% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass background checks for you and your dog’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.






