Pet Sitting Winchester Estates
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
Over 5 pet parents in Winchester Estates have booked pet sitting
Winchester Estates, 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: I have hands-on experience caring for my own dogs, Koda and Eddie. Koda is a Cane Corso puppy, which has helped me learn the importance of patience, consistency, positive reinforcement, and proper exercise. I make sure my pups receive plenty of love, attention, playtime, and daily care while keeping their safety and comfort a priority. I understand that every dog has a unique personality and needs, and I would treat every pet in my care like family! 🐶❤️ Pet care is something I enjoy and make time for in my daily schedule. I strive to be flexible, dependable, and attentive to each pet’s needs, ensuring they receive plenty of exercise, attention, and care. I communicate with pet parents to coordinate schedules and make sure every pup gets the time, love, and attention they deserve! 🐾 I prioritize safety, patience, and trust when caring for every pet. I make sure each animal feels comfortable, loved, and secure while following the owner’s instructions and respecting each pet’s unique needs. I believe in keeping open communication with pet parents, providing regular updates, and creating a safe, welcoming environment where both pets and their owners can feel confident and at ease. My goal is to treat every pet like family! 🐾❤️
“Heather was fantastic Lola seems happy and ate most of her food which is unusual when she's alone so she must have been to have Heather come by and thanks for all the pictures”
About: I’ve taken care of dogs my entire life whether that is my own dogs at home or helping out a neighbor or friend! I would love to help your dog as well I’m currently a student at Salisbury university but I am commuting so I only have classes on Tuesday and Thursdays. I am available almost any other time besides then! I will be there for whatever your pet needs may be! I love taking care of dogs of all sizes and know what it takes to make sure they will be ok while you are gone
“I needed a last minute sitter just to stop at my house and feed my dog this last weekend (mind you- he’s a German Shephard/Lab- he’s a big boy!) breakfast and take him out to go potty. I have been hesitant to use a kennel, as my dog was severely bit a few months ago. So I turned to Rover- Brooke was luckily able to pick up the job at the last minute and help out! She met with me the day before, we video chatted and she was understanding of Ace’s routine and our home guidelines. She has tons of experience with dogs! I highly recommend Brooke & will be using her again!”
About: I love playing with dogs and walking them. I've grown up around all types of dogs small and large. I'm very fun and outgoing as well as criminal justice trained ensuring your pets safety. I have taken care of our families dogs as well as watching other family friends pets. I have watched animals with allergies and medication needs. Dogs of all ages are welcome. I will meet any needs of the dog/dogs and ensure to have them back to you safe worn out and happy. I work part time so most of my day is running errands or cleaning the house. If they love car rides they are more than welcome to drive around with me. I will adjust my schedule to meet the needs of the dog or animal. Also absolutely love my kitties. Open to all animal requests just ask! Im a full time optician and part time cook. With plenty of notice I will take off my parttime job to care for your babies. Your pet will be loved as family. Your pet will be able to sleep with me and get full access of my apartment. Toilet bowl lids will always be closed
“Wonderful experience with Bo! She was friendly, responsive, sweet and we caring. Also flexible when our travel plans changed not once, but twice! Would definitely book with Bo again to care for our cat.”
About: I’ve taken care of dogs and cats my whole life and now I frequently walk, cat/dog sit, and board occasionally in my home. I thoroughly enjoy meeting new furry friends! Im currently working full time but have availability all throughout the day variating some days. For the most part afternoon times are best for the week I care for clients pets exactly how the wish for me to. I never want to impose my own beliefs on an animal that is not mine.
About: I’ve been dog walking and sitting for neighbors since I was 12 years old. I’ve dog sat multiple types of dogs. I’ve done dog walking, check-in & potty break visits, and I’ve stayed at a clients home for long periods of time (5+ days) to be with their pups. I’ve also been tasked with administering insulin shots to dogs before. And I have a lot of experience with dogs that have anxiety, whether with new people, thunderstorms, or anything else, as I have one myself and a long remaining client of mine does as well. I’ve always loved dogs, having grown up having 2 smaller dogs myself. I am hoping to do pet sitting as a new permanent business, so I will have nothing but time to look after your pets! I will schedule out days and time periods based on client necessity and to provide the optimal care for your pets. Because I have two dogs myself, one of which has severe people and other animal anxiety, which for the safety of your pets and mine means I am unable to bring any pets into my home as of current. However, I’ve stayed at the homes of clients before to be with their pups while they’re away. I feed them every morning and night or make sure the food bowl is full depending on how the client feeds their dogs. I give them any medicine or joint tablets that they need to be well. I let them out multiple times a day whenever they need it. And I try to play with and pet them as much as I can while I’m there so they don’t miss their humans too much. I will even take them on a walk if allowed.
About: Active Dog Loving Grandparents We enjoyed the pleasure of having pets our entire lives, they have brought us a sense of peace and joy and best of all unconditional love. Our best friends have been Boston Terrier’s, German Sheppard’s, American Bulldogs and Boxers. They are all unique in their personalities but all love to be loved, just like us. We are retired so one of us are at home all the time. We live on a great fence property with an awesome nieghborhood that we love to take walks around multiple times a day (weather permitting.) The dogs usually have a grand time taking a run around the property and playing. Should it be too warm of course they enjoy the air conditioning ? Now that our children are grown and married with children/dogs we occasionally keep their Boxer brother (Duke) and sister (Honey) and our grandchildren too. You can feel safe leaving your pets in our care. We will look after them and love them like our own! In fact, they may not want to leave as our grand-dogs do? Can provide a bath prior to your return if you would like. Look forward to meeting you and your baby soon. Grandma J
“Crystal was a great sitter. We have 4 different breeds of dogs, (including a puppy and a senior) and she was able to meet all of their individual needs. She was on time and communicated regularly. I felt very comfortable leaving the dogs in her care.”
About: As a lifelong pet lover and pet owner of over 11 years, I understand that pets are family and deserve the same love, patience, and attention we give our own. While I'm new to Rover, I bring years of hands-on experience caring for pets, including senior dogs and raising and training my Doberman, Brody, over the past three years. As a full-time architect, I'm detail-oriented, organized, responsible, and a fast learner. I understand the importance of following instructions carefully, maintaining routines, and making sure every detail is accounted for. Whether your dog needs a leisurely walk, extra patience and care in their senior years, or simply a little extra love and attention while you're away, I'll do my best to make them feel safe, comfortable, and cared for. I'm committed to being reliable, communicative, and respectful of your pet's individual needs. I know how important it is to trust someone with your furry family member, and I look forward to building that trust with every booking. I can't wait to meet you and your pup! I work full-time as an architect, but I'm happy to incorporate pet care into my daily routine! I'm available for walks and drop-in visits before my workday begins and during my lunch break, with additional availability outside of my regular 9–6 schedule depending on the day. Your pet's safety, comfort, and happiness are always my top priorities! I live in a welcoming, family-oriented community with accessible walking paths and plenty of green space to explore and enjoy. It's a great environment for daily walks, fresh air, and outdoor adventures, not to mention it is walking distance to Quiet Waters Park, which includes a dog park/beach. My Doberman, Brody, is a friendly companion who may be able to keep your pup company, provided they're a good fit for one another. As an experienced pet owner, I understand that every dog has their own personality, boundaries, and comfort level, and I'll always prioritize their individual needs.
About: As a dedicated dog walker and in-home pet sitter with over two years of experience, I know how important it is to find someone you can truly trust with your pet. I care for every dog (and cat!) as if they were my own — with patience, love, and attention to their unique needs and routines. What You Can Expect: ✅ Safe, fun, and tailored walks ✅ Home visits that follow your pet’s schedule ✅ Clean water, food, meds (if needed), and lots of affection ✅ Daily photo updates and messages so you never have to wonder how things are going ✅ Respect for your home and your pet’s space I’m trained in basic pet first aid and always check collars, leashes, and gates before heading out. Whether it’s a quiet walk or an energy-burning play session, your pet's safety and happiness are always my top priority. Let’s schedule a meet-and-greet! I’d love to learn more about your pet and how I can help make your time away stress-free for both of you. 🐶🐾 Pet care fits naturally into my daily routine because of how flexible and rewarding it is. Since I set my own schedule, I can book pet care clients around my part-time job shifts and study blocks, which helps me stay balanced and productive. Walking dogs gives me a much-needed mental reset from screen time and studying, and it keeps me active throughout the day. It’s also a great way to supplement my income without taking on another traditional job. Most of all, spending time with animals brings me a lot of joy and motivation — it breaks up long study days and reminds me why I love what I do Whether you’re at work or away for a few days, I provide reliable, in-home care that keeps your pets safe, happy, and stress-free in their familiar environment. From daily walks to feeding, playtime, and medication routines, I tailor every visit to your pet’s unique needs. 🔐 Safety & Professionalism Equipped for pet first aid always carrying a kit Detailed home-entry and security protocols Leash and harness checks before every walk Weather-conscious and always alert to potential hazards Respectful of your home, your pets, and your time 📸 Peace of Mind After each visit, you’ll receive a photo and short update so you know how your furry friend is doing — because trust is built on communication
“Our cats felt very comfortable with Michael, and so did we! He's reliable, kind, and respectful of animals, and also very intuitive with them. Their personalities are very different, but he gave Bagheera plenty of active play and made friends with the very shy Laska. We highly recommend Michael and will use him again. Great Rover cards, by the way!”
About: Hi, I'm Michael, a dependable pet lover in the Pasadena, MD area. I offer dog walking and drop-in visits, and every visit includes fresh water, feeding on your schedule, potty breaks, playtime, and a quick photo update so you know how your pet is doing. I have been a pet owner ever since 1995 and am comfortable with all sizes and types. I'm careful and patient and treat every pet like family. I'm available during the week and most hours and I live close by, so I can be flexible for last-minute visits. I have reliable transportation and I always show up on time. I'd love to meet you and your pet before the first booking so we can go over routines, quirks, and anything special they need. Thanks I am currently working part time doing deliveries and pet care. I have a full fenced back yard and a basement if crates are needed but prefer to keep animals out of crates. I have a fenced in yard and my house is sectioned off top and bottom, as well as rooms that can be used for the animals as needed.
About: I’ve taken care of dogs and cats since I was very little! From bottle feeding kittens and newborn puppies, to the older furry friends who need extra attention in different ways. I currently am a stay at home mom to a very friendly and pet safe 4 year old. We take everyday as a new adventure which allows plenty of flexibility. From tasks as serious as medication administration and special diets to as simple but important as preferred toys in their beds so they sleep just like they would if you were home, I will be more than happy to care for your pet as my own.
About: I have a one year golden retriever who I raised on my own since he was 8 weeks. I’ve also have experience pet sitting, walking family and friends animals throughout the years I’m currently working full-time on the weekdays and attending AACC gnursing school starting in August . However I have open availability to watch your fur babies all through out the weekend! I have a friendly golden retriever boy to keep your fur babies occupied. I’ll be home majority of the day to keep them comfortable and safe.
“Shawnna took great care of our kitty during our trip. She was very conscientious, communicative and left our home very tidy. We would love to have check in on our sweet girl again!”
The median cost per visit for pet sitting in Winchester Estates is $20
Pet parents share their Rover experiences - Winchester Estates
Maranda took excellent care of my two cats while I was out of town. I never had to worry and knew they were in great hands. She was kind, communicative, very reliable, and always went the extra mile. Would rebook again in a heartbeat. I really can’t thank her enough for the peace of mind she gave me! Highly recommend!
Kaileigh was an excellent cat sitter for our 2 cats. She was professional with the duties and affectionate with our cats. She made it less stressful to be away from them while we were on vacation. I would highly recommend Kaileigh and we will be using her again.!
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 Estates
Select a filter and find qualifying sitters offering pet sitting.Sitters in Winchester Estates average 6 repeat pet sitting clients
FAQs for Pet Sitting - Winchester Estates
Frequently asked questions about Rover
The average cost of Pet Sitting in Winchester Estates is $16 per visit as of November 2026. Most bookings cost between $16 and $16 per visit. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of November 2026, there are 2,296 sitters on Rover offering Pet Sitting across Winchester Estates. Enter your ZIP code to see which available sitters are closest to your home.
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 with handling special pet needs in Winchester Estates. On Rover:
- 88% of sitters can help with special care needs
- 93% can help with giving oral medications or injections
- 95% 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 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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