Pet Sitting Windsor

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Over 4
pet parents in Windsor have booked pet sitting

Windsor, Find top rated pet sitting

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Mia M.
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Mia M.
from
$15
per visit
1 repeat client
3 years of experience
Suffolk, VA, 23434

I submitted a last minute request for drop-in visits and Mia accepted without hesitation. My pups warmed up to her right away and loved all the pets and attention.

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Brianna P.
Sitter Profile Image: Nikolaas P.
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Nikolaas P.
Star Sitter
from
$10
per visit
5.0 out of 5 stars
33 reviews
7 repeat clients
15 years of experience
Franklin, VA, 23851

Nik is a true professional who genuinely cares about the pets he’s visiting and has so much knowledge to share! We have a senior mixed breed who is nervous around new people and Nik was patient with us (as we were using this service for the first time) and our girl who was understandably a little anxious about someone new being in her house. He has amazing communication skills and is incredibly reliable.

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Ciara M.
Sitter Profile Image: Caprice G.
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Caprice G.
from
$15
per visit
12 years of experience
Windsor, VA, 23487

About: What sets me apart is the genuine love and experience I bring to every pet I care for. I have over 12 years of pet-care experience and am a pet parent myself to three Chihuahuas, including a senior dog. Because of this, I understand the extra patience, attention, and care that senior pets can need. I’m comfortable caring for puppies, adult dogs, and senior pets, and I’m happy to accommodate each pet’s individual routine and personality. Whether your pet is energetic and playful or prefers a quiet, relaxed environment, I’ll make sure they feel safe, comfortable, and loved while you’re away. 🐾❤️ Pet care fits naturally into my daily routine because I stay home full-time. This allows me to give pets plenty of attention, companionship, playtime, and care throughout the day. I’m able to work around each pet’s normal routine, including meals, potty breaks, walks, medications, and plenty of love and cuddles. 🐾❤️ Because I’m home most of the day, your pet can have someone nearby rather than being left alone for long periods. I truly enjoy having animals around and love making them feel comfortable, safe, and at home while their families are away. I care for every pet based on their individual needs and the routine their family has established. In my home, pets are treated like family and receive plenty of attention, playtime, potty breaks, walks, meals, and lots of love. When caring for pets in their own home, I make sure to keep their normal routine as consistent as possible so they feel comfortable and secure. I’m happy to provide walks, feeding, fresh water, litter box care, playtime, cuddles, and basic medication care when needed. I understand that every pet is different, so I take the time to learn their personality, schedule, and specific needs before their family leaves. My goal is always for your pet to feel safe, loved, and well cared for while you’re away. 🐾❤️

Sitter Profile Image: Christian G.
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Christian G.
from
$25
per visit
5.0 out of 5 stars
2 reviews
8 years of experience
Suffolk, VA, 23434

Christian did a great job with our cat drop-in visit. He was on time, made sure their water was topped off, spent time playing with them, and sent plenty of pictures and updates while we were away. It was obvious he genuinely cared about making sure they were comfortable and cared for. We’d definitely book with him again and highly recommend him to anyone looking for a reliable sitter.

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Shelby H.
Sitter Profile Image: Brooke R.
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Brooke R.
from
$20
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
6 years of experience
Smithfield, VA, 23430

About: I have been around dogs my entire life, and caring for them has always come naturally to me. I’m a compassionate and attentive caretaker who truly understands that every dog has its own personality and needs. Whether it’s making sure they’re fed, walked, played with, or just comforted, I treat every dog as if they were my own. My lifelong experience has taught me patience, responsibility, and how to build trust with animals, which is why I know I’d be a great fit for any role involving dog care! i promise your dogs will love our fenced in dog area and have lots of fun! I am currently not working, and I have always wanted to work with animals! Dog sitting allows me to watch my own dog while also taking care of other people’s dogs and making a living for myself! we have a fenced in dog area and lots of room to run and play! I don’t allow any squeak toys in my house in case of choking hazards! And I have crates if you can’t bring your own if your dog is crate trained!

Sitter Profile Image: Shae M.
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Shae M.
from
$30
per visit
5.0 out of 5 stars
21 reviews
7 repeat clients
7 years of experience
Suffolk, VA, 23434

Amazing. Was incredibly flexible and caring. We needed too book a sitter with less than 24hrs notice and she was our hero. Thank you so much.

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Layla V.
Sitter Profile Image: Chainey L.
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Chainey L.
Star Sitter
from
$14
per visit
5.0 out of 5 stars
15 reviews
4 repeat clients
5 years of experience
Wakefield, VA, 23888

Chainey was great and was so good with my pups and she even was able to come an additional morning since our flight was delayed! Def recommend!!

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Brandie L.
Sitter Profile Image: Abigail T.
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Abigail T.
from
$20
per visit
4 years of experience
Windsor, VA, 23487

About: I have had dogs and cats in my life since i was a baby! They have always been my bestfriend! I currently have 1 dog (a golden retriever) and 2 cats. And I’ve house sat for many many fiends for long periods of time. In my eyes i don’t see them as just animals but another member to the family. And that’s how i would treat your fur babies! You should feel comfortable leaving your fur babies in the hands of someone else when life becomes busy or you just need to get away. and i promise I will give your babies all the love and attention they deserve! I work weekdays but i get off early almost everyday with very flexible hours and I’m off every weekend. My work schedule is pretty flexible. I have loads of free time! I have a fenced in yards. My dog is an inside dog (the house belongs to her lol) i have 2 cats that wants to sit on everyone lap. My dog has full access to the house when I’m home and only the downstairs when I’m gone. The cats roam the house as they please but they love to be by my side more than anything! My dog spends so much time outside playing and gets a long walk every day!

Sitter Profile Image: Robbyn W.
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Robbyn W.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
15 reviews
7 repeat clients
3 years of experience
Suffolk, VA, 23434

Robbyn is so amazing and patient. My fur babies didn't come out from hiding but she was very understanding about it. I truly appreciate her!! And will definitely book her again!! Thank you Robbyn!!

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Tarsha N.
Sitter Profile Image: Jamie K.
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Jamie K.
from
$32
per visit
5.0 out of 5 stars
3 reviews
2 repeat clients
20 years of experience
Suffolk, VA, 23434

About: With over 20 years of experience caring for pets, I’ve had the privilege of working with a variety of animals, from dogs and cats to more exotic pets. My passion for animals has allowed me to develop strong skills in pet care, including administering medications, feeding, and ensuring a safe and loving environment. I’ve worked with pets of all ages, providing personalized care to meet their unique needs. Whether it's a daily walk or just some extra love and attention, I treat every pet like my own! As a stay-at-home mom, my schedule is flexible and always open to accommodate your pet sitting needs. I’m home full-time, ensuring your pets get the attention and care they deserve whenever you need it. Whether it’s last-minute or planned, I’m here to help! I will care for your pets with the same love and attention I give my own small dog. With a fenced-in backyard, your pet will have plenty of space to play and explore safely. I provide regular exercise and lots of cuddle time to ensure they feel comfortable and happy. Whether in my home or yours, I will follow a personalized routine to meet your pet's unique needs and make sure they feel loved and cared for.

Sitter Profile Image: REBECCA W.
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REBECCA W.
from
$16
per visit
5.0 out of 5 stars
13 reviews
5 repeat clients
20 years of experience
Suffolk, VA, 23437

Rebecca did an amazing job caring for justice. She made sure to cater to her every need, even adjusting times when needed. I usually kennel justice when I go away so this was my 1st time using this type of service and I couldn’t be happier. Thank you Rebeccah for taking such good care of my baby and calming my nerves.

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Felicia N.
Sitter Profile Image: Madison T.
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Madison T.
from
$17
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
13 years of experience
Suffolk, VA, 23434

Awesome sitter. Was very patient and considerate of our baby girl and took well care of her. Also was very helpful and flexible in a last minute change to schedule. Definitely will be picking Madison again on any future trips to watch our pets

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Rafael K.
Sitter Profile Image: James C.
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James C.
Star Sitter
from
$30
per visit
4.9 out of 5 stars
57 reviews
16 repeat clients
15 years of experience
Suffolk, VA, 23438

Did a great job with our doggie! Seemed like he really cared by the notes and interactions that were had with my dog. Communication 5/5 love for animals 5/5 overall first experience with this app he definitely made the experience great knowing our dog was taken care of while we were gone for our short vacation. Highly recommend

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Jacob C.
Sitter Profile Image: caleigh j.
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caleigh j.
from
$13
per visit
5.0 out of 5 stars
3 reviews
9 years of experience
Carrollton, VA, 23314

Caleigh did a great job with a young puppy and giving his meds to him. Highly recommend and will use her again in the future.

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Bj B.
Sitter Profile Image: Melody & Matthew D.
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Melody & Matthew D.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
83 reviews
43 repeat clients
10 years of experience
Suffolk, VA, 23434

Melody has done a great job of taking care of Victoria. We are pleased to have her. I feel very fortunate to have Melody and Matthew taking care of our Victoria

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Jay B.
Sitter Profile Image: Chad H.
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Chad H.
from
$30
per visit
10 years of experience
Windsor, VA, 23487

About: Hello there! My name is Chad, and I love pets. Dogs, cats, or rodents, I enjoy being around them all. Personally, as this is a dog walking app, I have never owned a dog, but I have always gotten along great with any that I have ever met. I do, however, own cats. In my lifetime I have cared for 3 different ones, 2 are now with my mom while I care for my own cat, Charlie. All 3 love me greatly, and get excited every time they see me. Just like your animals will. I also help care for my 2 of my roomates' cats. So, no matter who's pet it is, I will greatly enjoy the company. I cannot wait to meet your dog(s), and any other animals are a plus.

Sitter Profile Image: Jane C.
Verified Enhanced Background Check
Jane C.
from
$40
per visit
5.0 out of 5 stars
9 reviews
1 repeat client
17 years of experience
Suffolk, VA, 23434

About: My first two pets were 2 doggies at 9 months old. I had them for 17 years until they left for doggy heaven October 2024 and February 2025… I am not ready to fully commit again quite yet so decided babysitting and loving on others’ furbabies will help the healing. Work from home all week. Will be able to take care of them in home and overnight if needed! I will accomodate to all requests and needs. Will appreciate details such as age, allergies, health, likes and dislikes. Will treat your baby/babies like they are my own. Will walk them as I have a dog friendly neighborhood as well as a newly built dog park. The backyard is also fenced.

Sitter Profile Image: Lauren K.
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Lauren K.
from
$18
per visit
5.0 out of 5 stars
5 reviews
2 repeat clients
20 years of experience
Suffolk, VA, 23434

Lauren took care of my sweet Bailey like she was her own. From the moment they met, Bailey was completely smitten, and I can’t blame her. Lauren has this calm, loving energy that dogs (and people) instantly trust. She made sure Bailey was happy, safe, and spoiled with attention, and I never once had to worry. She’s attentive, patient, and somehow knows exactly what a dog needs before they even ask for it. I swear Bailey was happier than ever when I came back from work... probably because she spent her days with someone who truly loves the animals she cares for.

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Addie L.
Sitter Profile Image: Robert B.
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Robert B.
Star Sitter
from
$26
per visit
5.0 out of 5 stars
18 reviews
3 repeat clients
15 years of experience
Suffolk, VA, 23434

Robert was amazing with my two dogs! He kept me updated with photos and took great care of them while I was away. They were happy and relaxed when I got back. Highly recommend him!

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Jasmine N.
Sitter Profile Image: Trinity H.
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Trinity H.
from
$10
per visit
5.0 out of 5 stars
17 reviews
2 repeat clients
5 years of experience
Suffolk, VA, 23434

About: I've owned or help own several dogs. My family has 3 currently. I love animals so I volunteer for and ride horses, care for dogs and feed the feral cats in my neighborhood. I'm perfect for someone who needs a quick, cheap, consistent service. Currently available to walk or drop-in with pets from 2-5pm on Wednesdays only. I am a very good listener and a gentle handler. I instill some consistent walk etiquette but I am not a dog trainer! I am here to keep me and your pet walking and safe. I have a fenced in backyard and several parks nearby. My neighborhood is walkable. Your pet will never be far from water, food, space or comfort.

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The median cost per visit for pet sitting in Windsor is $20

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  • 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

  1. 1. Search

    Browse profiles of sitters near you who offer pet sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Popular requests for pet sitting - Windsor

Select a filter and find qualifying sitters offering pet sitting.

Sitters in Windsor average 6
repeat pet sitting clients

FAQs for Drop-In Visits - Windsor

Frequently asked questions about Rover

The average cost for Pet Sitting in Windsor on Rover is $13.91 per visit (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Pet Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Pet Sitting. For more information on service fees, click here .

As of September 2026, there are 2,252 sitters on Rover offering Pet Sitting across Windsor. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Windsor stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

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.

Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.

If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.

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 .

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.

Yes, you can find sitters who have experience with handling special pet needs in Windsor. On Rover:

  • 96% of sitters can help with special care needs
  • 99% can help with giving oral medications or injections
  • 98% 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.

A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

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