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
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Jannette and her partner is wonderful. I love the fact that they are always in communication about how my dog Venus is doing on a walk. They take great care of her.”


“Erin came and met my cats prior to starting. She was very responsive and friendly. She did great while we were away. She sent pictures and kept us updated everyday. Very reasonable and reliable! Would definitely recommend!!”

“Ifan is truly an exceptional dog handler, and I cannot recommend him highly enough. From the very first time we worked with him, it was clear that he brings both professionalism and genuine care to what he does. He is extremely experienced and knowledgeable about dog behavior, which immediately put me at ease as a pet owner. He takes the time to understand each dog’s personality, needs, and routines, and it really shows in how comfortable and happy the dogs are around him. What stands out the most is how naturally he connects with the pups. My dog can be a bit particular when it comes to new people, but with Ifan, the bond was instant. Over time, that connection has only grown stronger—my pup gets excited every time he sees him, which says everything about the level of trust and comfort Ifan builds. It’s such a relief knowing that my dog is not just being looked after, but genuinely cared for and understood. Ifan is also incredibly polite, respectful, and communicative. He keeps me updated, is always punctual, and is very flexible when it comes to scheduling. I’ve used his services repeatedly, and each experience has been consistently excellent. Whether it’s handling high-energy playtime, maintaining routines, or just giving the dogs attention and affection, he does it all effortlessly. Overall, Ifan goes above and beyond what you would expect from a dog sitter or handler. His dedication, kindness, and expertise make him someone you can fully trust with your pet. I wholeheartedly recommend him to anyone looking for reliable, caring, and professional dog care.”

“Aston has become our dog trainer and Rover sitter! My pups absolutely love him and he does an incredible job making sure they’re well cared for, all while reenforcing their training! Highly recommend his services!”

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 taken care of dogs since I was 8, from watching relatives dogs to neighbors across the street. I personally have two large German Shepards in Connecticut. I’ve volunteered at MSPCA in Boston and worked with puppies there. I’m very patient with dogs of all ages and activity levels! I am available all day! I am home for the summer after graduating college, so I have a lot of availability during the week and weekends! I have a very large living room with plenty of space for animals! I also have a large yard for them to walk around and love going on walks with dogs.
About: I do have veterinary experience. Have taken care of friends dogs for many years. Basic experience with grooming and nail trims. Also have cat care experience. I currently work early AM shift at my regular job. I am available after 11am for walks and check ins.I am unavailable on weekends at this time I have experience with giving medicine,oral and injectable. Feeding,and medication instructions will be followed to a T. If special accommodation is need,please let me know,so I can plan accordingly.

About: I have grown up with a family dog all my life and now have my own! I have loved and trained him since he was a puppy and consistently receive compliments on how he is such a good boy and how well-behaved he is! I have always enjoyed taking care of doggos for family and friends and am very excited to help take care of yours! I am very good with dogs of all ages including young puppies in their teething and potty training phase to senior dogs who want cuddles and sniffs. I am available for house sitting and will spoil your pet with attention, play time, and walks while you are off enjoying your vacation or trip. I am also available for drop-ins and walks! You can count on me to keep your pets safe and happy :-) I have a very flexible summer schedule and can keep your pets on the their typical routines! I am happy to follow any special instructions you have your doggo! Every pet is unique and my goal is to take care of your pet as you would so you can be care-free while you are away and sleep easy knowing your pet is in good hands. You can trust me to keep your pets safe and your home exactly as you left it. I will treat your home as if it was my own, just like your pet.

About: I’ve taken care of dogs and cats since I was 16 years old. I am now 22 with three cats of my own and a love for taking care of furry friends!!🐈⬛🐕 I am currently a college student available from 1-6:30 every weekday. After 4 pm on Saturday I am available and all day Sunday! My whole life I have been called an animal whisperer, as I get along with any animal I interact with. It brings me a lot of joy to care for pets and make owners feel secure in their decision to hire me. I am very detail oriented when it comes to their routine and will ask questions to confirm I am taking care of your pet correctly.
“Thank you so much for being patient w our Lily, Heather! We will definitely book again. You went above and beyond with communication and we couldn’t have asked for a better visit!”

About: I had my own wonderful dog for 16 years. My yard is spacious so your dog has plenty of room to run around and play. Big or small dogs are okay with me. I am an animal lover of all kinds and have experience taking care of other types of animals like rabbits, guinea pigs, and cats. PLEASE NOTE: I do not watch unspayed/unneutered dogs I will charge a late fee if you are 30 minutes over the agreed ending time I am a full time student who takes my classes online. I have a flexible schedule so I have plenty of time to get outside to walk and play with dogs. I do have a fence in backyard. My backyard has plenty of space as well for your dog to explore. I am a big animal lover and I have multiple years of experience taking care of them.
“Went on vacation for a week and needed someone to feed my cats every night. My cats are pretty unique so the feeding procedure is not the easiest. Followed every detail to the T. Very grateful!”

“Shannon took great care of our fur babies while we were away. Litter box was cleared and furballs picked up! Kitties were very happy to have her visits and give pets! Would absolutely use her service again! Great communication 👍🏽”

About: I’ve been around dogs all my life, and adopted a pug of my own 12 years ago, so I understand what an important part of the family pets are. I’ve watched dogs from 2 months to 14 years old, from an overweight chihuahua to an old Great Dane. Currently I have a labradoodle and French bulldog that I’ve raised since they were puppies. Currently working from home, so I have time to pop in and check on your pups, or dog sit on the weekends if you need. I will treat your pets like my own - walking them, administering medications, feeding them, whatever is needed. Happy to help take care of your pets.
“Jillian always takes such good care of our Peanut! She gives great updates and photos of our sweet girl when we are away and makes sure she is cared for, would recommend her highly to everyone!”

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.







