House Sitting Windsor
Find a loving house sitter to watch over your pets and your home.

Windsor, Find top rated house sitting
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

“Isaiah did a wonderful job babysitting our dogs and house! We came back and the dogs were not anxious at all and the house was clean. They were well taken care of and he sent many photos. Definitely will use again!”

“Sara was a lovely sitter! She was extremely communicative and sent lots of photos. We felt so comfortable with her watching our pup in our home while we were gone and we could truly trust our dog was in good hands. We came home to a spotless house! She’s going to be our new go-to. Thank you so much Sara!”

“Cheyenne did a wonderful job caring for our 3 aussies in our home while we were on vacation. She was very responsive and responsible. We will definitely hire her again for our pet care needs!”

“One of a kind! Kendall is incredibly reliable and a wonderful communicator. We felt our animals were in good hands the entire week. Last minute our cat got an infection and she didn’t bat an eye to administering his medication daily. Our cats were both relaxed and happy when we got home, plus the dishes were done and the house was tidy!”


“Douglas was such a great pick to hang with our pups and care for our home while we were gone. Our pups like to keep things interesting and Douglas’s patience with them is not only appreciated, but is admired, especially when it came to caring for our senior dog. We would gladly welcome Douglas back to our home, and I know the pups would love that too.”
“Thank you Marissa! Figgy was well cared for and were so thankful to be able to leave her at home instead of at a kennel. Marissa left the house spotless and was extremely flexible when our plans changed.”

“This was my first time hiring a pet sitter and Kaylynn couldn’t have been more perfect. She kept me updated, consistently checked in regarding my travel plans to support with care, provided quality care and walks and snuggles to my furbabies. I am so grateful for Kaylynn and will definitely hire her again for future pet sitting needs.”


About: Hello! I’m a lifelong dog lover with years of experience caring for dogs of all sizes and breeds. I grew up with a German Shepherd and was one of his primary caregivers, taking him on walks, arranging playdates, and providing his daily care, including administering medications. I also volunteered at a local dog shelter for several years during undergrad, where I regularly walked and cared for a variety of dogs. Outside of my own experience, friends and family often rely on me to check in on their dogs and house-sit for extended periods. I’m comfortable with dogs of all personalities and sizes and will treat your pup like my own! I am currently a student, so my schedule is flexible. My weekends and evening are open for house sitting or dropping in for walks for your puppies! When at your home, I make sure to keep a tidy environment and return all items used back to their original spot cleaned while giving your furry friends love and enrichment with walks, tug-a-war, and more!
“Jenna is amazing! She took such great care of our 3 dogs and even taught them new tricks! She is extremely communicative and sent us photos and videos often. She left our house spotless and even watered my plants for me. She is now our go to person!”


“Emily did a fantastic job caring for our critters and home while we were away. She provided daily updates, photos, and even a video or two. We really appreciated her good communication and reliability. Thanks for a great experience!”


“The other reviews are correct Andrew is amazing! He took care of my pup while I was away but also took care of my home like it was his own. He sent updates with pictures and his communication was simply great. I'm so happy I found someone who I can trust to look after my dog and home while I'm away. I cannot say enough good things about Andrew and I will be booking him a few more times this year. Thank you Andrew!”

“Victor was an exceptional guest and a wonderful caretaker for my two dogs. He followed all instructions carefully, maintained great communication while I was away, and most importantly, my dogs absolutely adored him. The house was spotless when I returned! Victor went above and beyond to ensure everything was in order, and I felt completely at ease knowing my pets and home were in such capable hands. I would not hesitate to welcome him back again. Highly recommended!”

About: I have had at least one dog all of my life. Often times more than one. Currently living with just one Lab who would love a visitor/playmate. I foster emergency overnights on rescue transports. I have been a caregiver for dogs of all ages and kinds; puppies, senior dogs, and dogs with separation anxiety. I have grandcats I house sit for and have also taken care of chickens. I work from home with tons of flexibility. I have one adult child at home in graduate school, they have a health condition which keeps them home most days too, so your pet is never short of human companionship. I live in a great neighborhood for walks on a leash. I provide dog sitting in a one story home with a large, wooded fenced yard in central Richmond neighborhood. Great for dogs of all ages and abilities. I live with one Lab that's a large couch potato. He also likes his human to sit outside with him rather than be out there all by himself. So we spend lots of time outside together. Pets are permitted on furniture and the bed, whatever makes them feel at home. I do have a large dog crate that can be set up if needed, but only if requested as it will put your pet at ease. The most important factor is making sure your pet feels comfortable, keeping their routines and habits to lessen the stress of a new place.

“Melanie was amazing! She watched our dog for the weekend, and saved us after another sitter had cancelled. She was communicative and kept us updated the whole time with photos and videos. She’s super sweet and reliable. We will definitely book her for future stays.”

“Alex did a great job with our 2 pups. He took detailed notes at our meet and greet and followed their feeding and walking schedules carefully. Great communication and pics so we knew they were receiving good care. We’ve already booked Alex for our next time away”

“Kira was amazing with our beagles. Kept in touch, took care of everything, and treated them like her own. We were so pleased with how well she cared for Luna and Neko and look forward to booking with her again. Excellent sitter and Luna and Neko’s new best friend!”

The median cost per night for house sitting in Windsor is $50
Pet parents share their Rover experiences - Windsor
Emily stayed with our pup while we were away for our first anniversary trip. She is, without a doubt, the best sitter we have ever had for Kobe. Not only did she send pictures every day, she took him on walks at the park, monitored his eating habits, brought in our mail, and came to the rescue when the breaker flipped and AC went out. We came home to a calm and happy pup! We are so grateful for her and trust she’ll be great with your pets too. Kobe can’t wait until he sees her again 🥰

Kendall was beyond friendly and responsible. She was extra caring communicating with us before we booked with her, sending her ETA when she came for a meet and greet when we were looking for a house and dog sitter. Kendall is the perfect house sitter as she is self employed and therefore can do a lot of work from home. She let us know exactly when she had outside commitments such as business meetings so we knew our pup would have plenty of company while we were gone. She also asked many questions to make sure she knew exactly what we were hoping for in terms of care. We received many updates and photos while we were gone and Kendall sounded like she generally enjoyed everything about taking care of our pup. Kendall left our home in spectacular condition. Thank You Kendall!

I recently had Estella watch my dog, Levi, for a full week, and I couldn’t be happier with the experience. Levi is an overly anxious, high‑energy, and sometimes reactive dog, so leaving him with someone new is never easy for me. Estella handled him beautifully. He seemed calm, comfortable, and well‑cared‑for the entire time. Her communication throughout the week made a huge difference. Because of her thoughtful check‑ins, I was actually able to relax and enjoy my vacation. When I returned home, my house was in perfect shape, and Levi looked great. I highly recommend Estella to anyone looking for a reliable, kind, and capable pet sitter. She gave me peace of mind and took wonderful care of my boy.
Alexis is wonderfully attentive and communicative and did an excellent job with our senior dogs! We were gone for a week and knew they were in good hands. She was very receptive to our directions and keeping the little old ladies safe and loved. We highly recommend Alexis!
Molly took great care of our three dogs while we were away and kept us updated throughout. Molly was especially patient and understanding with our older Chihuahua. It was clear that our dogs were well cared for and comfortable. We would happily trust her with our pets again and highly recommend her to others.

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 pets like family

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