Pet Sitting Winchester
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
Winchester, 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.
About: IMPORTANT— I will be in Connecticut from 12/20-1/3. All other dates I will be in Indiana. Unfortunately there is no way to specify location for specific dates in Rover. If you have any questions please let me know! I have taken care of pets my whole life (my own and others). I have two of my own dogs currently — at 70 lb Shepherd x Dalmatian and a 25 lb Jack Russel x Aussie, both of which can get rowdy so I am no stranger to high energy pets! I am happy to help work on basic commands and will make sure your pet gets plenty of physical and mental exercise! I am a graduate student so my schedule is very flexible when it comes to checking in on pets and I typically like to spend >1 hour with them a day. I can provide medications and/or any specific care that your dog might require. I am a graduate student and my schedule can be flexible! For boarding— my own dogs wake me up at 6 am to eat and then often like to go outside around 8 after some more snoozing. As a student I can be gone from 9-5 occasionally, but more often it is 11-4 or something similar. On average I am gone between 4-8 hours at a time depending on my schedule. During the day we usually play and I give them different enrichment toys. When I am home I let the dogs out frequently to romp in the yard! Dinner is around 5 and then usually a calm evening. My weekends I am usually home for the entire day. For at home visits or walks— I am happy to fit your pets needs into my schedule! I can offer up to 3 visits per day and can spend various amounts of time with your pet based on their needs. For boarding—I have a fenced in yard with plenty of room to run and play. I have two dogs who are friendly (albeit loud) and would love to run around with your dog! I do have a crate in the house for your dog if needed. When I am gone my own dogs are closed in my bedroom and I would likely close your pet(s) in a separate room as well— your pet does not need to be crate trained if they are non destructive! Because I do have pets of my own any boarded dogs need to be dog and cat friendly. For home visits and walks— I am slow to introduce myself with each visit to make sure your pet is comfortable with me in their home as it can be stressful!! I typically sit with pets before immediately going for the leash to make sure they feel safe. I am happy to spend time with your pets beyond walking/feeding! In am able to stay for longer periods of time in the evenings to play or sit and just spend time with them. I am comfortable with reactive dogs and will prioritize your pets comfort.
“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!”
“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!”
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!
“Lynsey was absolutely sensational!!!!!!! Her care of Pooh Bear (my cat) was outstanding, as was her care for my home. She followed directions to perfection and was incredibly polite and professional. I highly, highly recommend her!!!!!!!!!”
About: I have been watching animals since I was 12 years old. Taking the neighbors pets for a walk, feeding them, or just checking in on them. I also have my Animal Control License and have been an ACO for 2 years now. I love it. I have a passion for animals and will do anything to make sure your fur babies are well kept and safe. I do work full time during the day M-F so midday check-ins are a little hard but morning and nighttime services are always easy for me to accomplish! I typically watch the animals in their own home just so they can stay within their routine. I never want to make the owner or animal feel uncomfortable ever.
“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 have been around dogs my whole life, I took animal science in High school and worked in dog related jobs for about 5 years. I currently have five of my own fur babies. 3 pups and 2 cats I currently am out of work for the summer and I have open availability. Late August I will return to work as a preschool teacher and will be available evenings and weekends. I will take care of your dog as if they were my own, following all the requirements that you set up before hand. Giving your dog all my attention and love.
About: I've been taking care of dogs since I was 8 years old and got my very first dog. I love all types of dogs, I can even handle aggressive dogs with ease! I always love to spend my free time with animals. Any availability I have is used to to go towards my pets and hopefully yours! I never let animals I don't know very well be off leash outside without my supervision, it is dangerous to me to be careless like that. I never take it too fast and id love to scedule a meet and greet.
“Ashley was awesome taking care of my babies one of them has extreme medical needs and she was great with her pictures were amazing. She cleaned my house. She cleaned the cat boxes. She’s very communicative. I will definitely ask her back again. She was timely and my babies loved her. Thanks dooo much Ashley”
“She was awesome taking care of our cats! She’s very good at giving oral medication so I felt comfortable with her giving meds to our boy. Thank you so much!!”
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 worked at animal hospitals for 28 yrs I’m reliable and good with peoples pets I can give meds if needed insulin as well I get lots of waging tails my way I prefer come to your home so your pet is more comfortable and has there familiar surroundings and all the things they’re used to toys their bowls, etc. I can stay the night if needed I like staying with pets at there home this helps also with stomach upsets and stress of being somewhere new and unfamiliar I like the pets to be able to keep there routine
“She did a wonderful job eith my cats. They did hide on her but if I had her a few more days I am sure they would have liked her. If there is ever a time when I need a cat sitter again, I will hire her again”
“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 taking care of my own pets for 6+ years. I make sure pets feel loved and well-cared for, whether it's playtime, feeding, or just giving them some extra snuggles. I understand that each pet has unique needs and preferences, so I adapt my approach to suit their individual personalities. Devoted and loving pet caretaker available around the clock. With a very flexible schedule, I can provide frequent walks, playtime, and feeding to keep your pets happy and healthy. I have a yard for your pet to play in with supervision. I have a small dog and cat that are friendly, But they can be moved to another part of the house if you prefer.
Pet parents share their Rover experiences - Winchester
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.
How to book pet sitting
1. Search
Browse profiles of sitters near you who offer pet sitting.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for pet sitting - Winchester
Select a filter and find qualifying sitters offering pet sitting.FAQs for Pet Sitting - Winchester
Frequently asked questions about Rover
Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.
You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.
Before booking, confirm:
- the timing, length, and frequency of visits;
- the care instructions the sitter should follow;
- which parts of your pet’s usual routine should be prioritized;
- how often you would like to receive messages, photos, or other updates.
Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.
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 administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies 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 request a Meet & Greet to walk your sitter through your expectations.
A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet .
sitters on Rover set their own cancellation policy , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
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