Pet Sitting Winsted
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
Over 23 pet parents in Winsted have booked pet sitting
Winsted, 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.
“Stacey was reliable and took care of our dog while we went on a last minute overnight get away. I would hire her again. ? She followed all instructions and sent pictures during each visit. Our dog seemed normally loud and barky when we got home! A sign that all is well?!”
“Jared did an amazing job with our dogs. We got constant updates and knew they were being well cared for. The communication right from the beginning was top notch. We will definitely use Karina and Jared again!”
“Hunter went above and beyond while caring for our three cats for this past week. When the storm was approaching, she texted me to see if I wanted her to put our water bowls in case the power went out. It did, and she did put water out. From the pics, I could tell that Emma warmed up to Hunter right away. Iris got her pills even though she was skittish. Thank you, Hunter, for taking care of the kids.”
About: What started as a personal challenge—overcoming my childhood fear of dogs—became a journey of love. By volunteering with service dogs, I discovered my passion for all kinds of dogs, big and small. Now, I bring that same warmth and dedication to caring for your pet. My Schedule is Flexible, Reliable, and Full of Love for Your Fur Babies! I work part-time, so I have plenty of time to dedicate to your pets. Most weekdays are wide open for visits, playtime, or overnight stays. Whatever your furry family member needs to feel happy, safe, and loved-i'm your sitter! Anxious or rambunctious, I'm patient and caring. Let’s make sure your pet gets the attention and care they deserve!
About: I absolutely love dogs all shapes and sizes, when you book with me your dog will be in a safe and loving environment with me. it’s important to me that any dog i’m with at the time will have a fun and enriching environment with me and the time we’re spending together. I have experience training puppies and pet sitting puppies. I’ve done extended petting sitting stays and have done petting sitting with multiple animals, i’ve done week long stays with 6+ animals, so I can handle a big crew if you have it. I have experience with farm animals and horses as well if that’s ever needed as well! I’m currently working part time at a doggie daycare and boarding facility, I absolutely love working with the dogs and am just looking to do some more in my free time. I look forward to hearing from you :) If you use me for pet sitting you can expect your dog to be fully safe! I will follow your directions and expectations to the tea because I know what it’s like to have to leave your dog with someone and not wanting to have to worry about your loved one
About: I’ve been dog sitting for people my whole life. From shitzu’s, to lab mixes. I also have two rescues of my own who I’ve worked very hard with to make comfortable and feel loved after there trauma. I am currently a full time teacher so I’m available mostly weekends. Come summer time, other than a part time job I’ll be available often. I have two high energy dogs who love to play. We do not have a fenced in yard, but it is large with woods all around. We also have a lead set up for dogs who are a flight risk.
“Tara is so professional and reliable. Her warm personality comes shining through. This is the second time Tara looked after our very shy cat, Charlie. We came home to happy cat. Charlie's space was tidy and clean. My husband and I have every confidence in Tara. We cannot say enough positive comments about her. We will ask for Tara every time we go away.”
“Theresa was so wonderful with our 2 dogs. We had her do drop-in visits at our home while we were away. She fed them, let them outside, gave them treats, played with them and sat with them for a while. She left pictures and videos each time and she was so great, highly recommend!!”
About: I grew up with dogs and have always loved caring for them. I currently have a mix breed, Marley who is my little sunshine. I enjoy hiking, running and watching cartoons with him haha. I know what its like finding someone who is trustworthy to care for my dog when I need to travel for work or personal vacation. It can be a bit stressful looking for a good sitter but I can assure you that your dog will be in good hands.
About: I have been an animal lover since I was 10 years old. I love dogs. hence the reason why I currently have 3 Siberian huskies! I currently work in the medical field, where caring for others is a huge part of what I do every day. That same caring nature carries over into my love for animals! I’ve always had a huge heart for pets and truly believe they deserve the same patience, attention, and compassion we give the people we love. I would love the opportunity to care for your furry family members and make sure they feel safe, comfortable, loved, and well cared for while you’re away\. Whether it’s walks, playtime, feeding, check\-ins, or just some extra cuddles and companionship, I’ll treat your pets like they’re part of my own family\. 🐾❤️ I offer a variety of pet care services to make sure your furry family members are happy, comfortable, and well cared for while you’re away! 🐾 I can provide dog walking, drop-in visits, feeding and fresh water, potty breaks, playtime, lots of love and cuddles, and companionship. I’m also happy to care for cats and other pets and can follow your pet’s normal routine and any special instructions you provide. My goal is to give you peace of mind knowing your pets are receiving dependable, loving, and attentive care while they’re with me.
About: I enjoy the outdoors and taking a walk. Your dog will have lots of play time, as well as fun, treats, food and water. I just like having a dog around to keep each other company so they are not home alone for long time period, you know getting into mischief we can do that together and have more fun haha. I currently do not have any dogs but will get one when the time is right. I have enjoyed and attended dog shows showing for obedience and agility(Dalmatians). I also attended and passed the canine good citizenship test with my first dog. My second dog was adopted and we did agility and was a lot of fun. A dog is a companion in which you meet other dog friendly people. I'm currently working full time but would have time to care for your fur kid/s before and after work, get mail, water plants, check house. I do not have a fenced yard so would take your fur kids out on a leash at your home or if fenced and you chose for them to be loose at your home.
“Lynsey is the best! She took great care of my pups and I would definitely use her again in the future! Some nice pictures of them during the visit, a detailed report, and message. It's hard leaving your fur family at home but it was made easier knowing they were in great hands with Lynsey!”
“Amanda was great! She was consistent and made sure my cats had everything they needed. Including taking care of cleaning the cat bowls and picking up after one of them got sick. She gave good updates. Would use again and recommend to others.”
About: I’ve been around animals my entire life and have hands-on experience caring for a variety of pets, including dogs, bunnies, and birds. Growing up with different types of animals taught me how to adapt to each pet’s unique personality, needs, and routines. I’m comfortable with everything from energetic dogs who need structured walks and play, to smaller animals that require gentle handling and consistency. I pay close attention to behavior, appetite, and mood to make sure every pet is happy, healthy, and comfortable. I currently have open availability, which allows me to be flexible and fully accommodate your pet’s routine. Whether your pet needs early morning visits, midday check-ins, or evening care, I can adjust my schedule to fit their needs. Because I’m not rushing between commitments, I’m able to give each pet focused, unhurried attention during every visit. I care for pets in their own home, where they feel most safe and comfortable. My approach is always needs-based, meaning I follow your pet’s routine closely and adjust to their personality. whether they need lots of interaction or a calm, low-key presence.
About: I’ve loved and cared for dogs of all kinds since middle school, walking and pet sitting for family, friends, and neighbors alike. I believe every dog deserves the same level of affection, patience, and care as my own, while also giving each one the individual attention they need to feel comfortable and happy. I work full-time during the week, typically until 4 p.m. Monday through Wednesday and until 5 p.m. on Thursdays and Fridays. I’m available for evening walks on weekdays, as well as full availability on weekends and holidays. I love spending my free time with animals, so pet care naturally fits into my routine and is something I genuinely look forward to. When caring for pets in their own home, I always ensure they feel safe and comfortable in their familiar environment. I follow their owners instructions closely for feeding, routines, and any special needs. I take time to build trust with pets through gentle communication and positive attention while remaining focused on keeping them happy and active.
About: I have grown up with pets in my house all my life! Whether it be cats, dogs, chickens, goats, you name it! We rescued all of our fur babies so I have seen and experienced a lot in the animal world. I am currently a full time college student and I work part time. I can drop in before school, before I go to work, and when I am out of work! I can also do other times as long as we stay in communication. As I will be doing drop in and walks I will keep your animals leashed at all times unless specified differently so there are no escapees. I love giving my fur babies treats so if you provide me with the certain kind your babies can have I will gladly give them a treat for being adorable!
“Ashley was an excellent sitter and visited our 3 cats, at our home, over Christmas! Excellent communicator and took great care of our pets (including one with special dietary needs). Our house is in the same condition as we left it and our cats are stressed free and happy. Thank you for taking such good care of them and taking time to play and send photos!”
About: With over four years of experience working with dogs, I understand what it takes to keep them happy, safe, and well-cared for. I spent a year working under a professional dog trainer who also boarded dogs, which gave me valuable insight into dog behavior, training, and care. Beyond that, I’ve grown up caring for dogs—taking them on daily walks, making vet trips, and ensuring they get the love and attention they deserve. I’ll treat your pet as if they were my own, providing them with the care and companionship they need while you're away! As a university student, I have a flexible schedule that allows me to dedicate plenty of time to pet care. Whether it’s morning walks, midday playtime, or evening cuddles, I can accommodate your pet’s needs while ensuring they get the attention, exercise, and care they deserve. Your furry friend will always be a priority in my routine! Your pet’s safety is my top priority. I provide attentive care in their home, following all instructions. Unfortunately, I cannot offer at-home services due to accommodation regulations.
The median cost per visit for pet sitting in Winsted is $24
Cat parents share their Rover experiences - Winsted
Stacey is such a trouper! She made it up to our place despite the treacherous road due to the snow storm. She took great care of our guys and even took pretty great photos of them every day. Leaving pets while we travel is stressful and Stacey was such a great sitter and took all of that worry away from us. We really appreciate her!
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
1. Search
Browse profiles of sitters near you who offer pet sitting
2. Meet In Person
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3. Book & Pay
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Popular requests for pet sitting - Winsted
Select a filter and find qualifying sitters offering pet sitting.Sitters in Winsted average 5 repeat pet sitting clients
FAQs for Drop-In Visits - Winsted
Frequently asked questions about Rover
The average cost for Pet Sitting in Winsted on Rover is $27.75 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 1,806 sitters on Rover offering Pet Sitting across Winsted. 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 Winsted 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 Winsted. On Rover:
- 97% of sitters can help with special care needs
- 96% can help with giving oral medications or injections
- 99% 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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