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.
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'm an animal nerd who adores being around all types of animals! I've developed my skills in reading dogs' body language and have cared for dogs that need medication treatments. I have volunteered at animal shelters during my college years and helped a surrendered cat, who was extremely nervous and scared, gain back her confidence; I even had her eating treats from my hand in only a couple hours! I'm extremely driven and passionate about the care of beloved pets because pets are a part of the family! I work Tuesdays - Fridays from 10AM to 5PM, but there are times where I have to work late. I'm usually off Saturdays - Mondays, but there are times where I have to work in the evenings on Saturdays and the afternoon on Sundays; I will always be off on Mondays. I'm attentive with animals and make sure their needs are met: food, water, meds. I will take your pet on their daily walk routine, make sure they have ample time to play outside, keep them entertained, and if permitted take them to local parks to keep them socialized.
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
“What a great experience. This was my forst time using Rover and Anna made it a great experience. She was communicative and great with my babies. Thank you so much Anna, will definitely use you again and again.”
“Jason is very good with our dog, Samson. He loves Jason and responds well on walks with him. Jason is very patient and knows how to handle him well with all of his puppy energy.”
About: I absolutely love animals. I currently have a black lab and I love to just spend time cuddling with her, or going for long walks. If possible, I try to bring her along (assuming they get along at the meet and greet). I’ve noticed that dogs can wear each other out a lot faster than I can, and probably have more fun doing it too. Maddie gets along with everyone and just loves to meet someone new. For your dog, I will treat him/her as my own. I will play with them and take them for walks. I have no problems cleaning up messes, sometimes accidents happen. Let me love and take care of your pet so you don't have to worry about them during the day. Why I love dog sitting I've always been an animal lover. I've had dogs all my life and had two of my own. They truly are the best things that ever happened to me. I’m very active, so I would spend as much time outside as possible with your fur baby. My experience administering medication: I am fine with administering medication, but would like to have the owner show me the correct way of doing it before I start.
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
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.
“Savannah was so friendly and helpful. She handled everything how i would have. My boys are pretty emergentic and cuddly- she was able to really help me feel at ease while we were gone. She did a wonderful job and we will be using her again for sure!”
About: I've always been great with animals, able to read them and good at figuring out what they need. I volunteered at Animal Welfare League of Queen Anne's County for several years starting in High School. I've worked closely with large animals with behavioral problems, so I'm down the handle whatever quirks your pet has. My schedule is very flexible, and I can usually provide services as needed when given prior notice. Anytime of day as well, within reason ofc. I'm very adept at reading animals behavior and figuring out when they need attention, when they need space, and good at gaining an animals' trust.
“She is very sweet and updated when there was any issues. It appears our pets enjoy their company and gave them the meals. She was on time for the majority and within the time range that’s appropriate :).”
About: I have cared for many animals over the past 20 years for friends and family & I have also had my own fur babies as well. I am currently a stay at home mom with full time availability. I am able to crate your animals at night if needed for sleep and give frequent bathroom breaks throughout the day. I will care for your pets as if they are my own & treat them like family while they are here!
About: I’ve cared for pets for over 14 years, including my own and those of clients, friends, and family. As a professional organizer and mom, I bring structure, empathy, and reliability to every pet I care for. I’m especially attentive to routines, safety, and emotional wellbeing—whether it’s a playful pup or a shy senior cat. I manage my own schedule, which gives me plenty of flexibility for pet care. I’m available for walks, feedings, drop‑ins, boarding, extended stays, house sitting and any other combination that suit your scheduling needs. Whether I’m caring for pets in my home or staying in yours, I prioritize consistency, communication, and routine so your pet feels safe and loved. I’m available weekdays and weekends, and I tailor my schedule to meet your pet’s needs. In my home, I have a fenced yard and two friendly dogs who enjoy company. If your dog is shy or reactive, that’s no problem — I have experience with all temperaments and can keep pets separate when needed. My home is clean, organized, and set up for comfort. I follow feeding and medication instructions precisely and keep pet parents updated with daily photos and messages. When I’m caring for pets in your home, I maintain your pet’s routine exactly as you prefer and treat your space with the same respect and care I give my own. I’m comfortable with multi‑dog households, anxious or storm‑sensitive pets, and dogs who need extra reassurance or structure. I keep your home tidy, manage small household tasks, and ensure your pet feels secure while you’re away.
“Nicole is an excellent sitter. She is reliable, takes great (and lots of) pictures, and is responsive to inquiries and messages. Our shy cat has seemed to warm up to her after just a few visits. We will continue to book with Nicole.”
“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!”
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.FAQs for Pet Sitting - Winchester Estates
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 .
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 , 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 .
sitters on Rover set their own , 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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