Cat Sitting Winchester Estates

Book a cat sitter to stop by your home to feed and play with your cat.

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Over 3
pet parents in Winchester Estates have booked cat sitting

Winchester Estates, Find top rated cat 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: Brigid S.
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Brigid S.
from
$20
per visit
5.0 out of 5 stars
4 reviews
18 years of experience
Chester, MD, 21619

Very friendly, knowledgeable, competent, reliable. Came to the house for last minute weekend care of our cats. Sent pictures during the weekend. We definitely recommend Brigid.

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zetasean s.
Sitter Profile Image: Bohdanna G.
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Bohdanna G.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
79 reviews
28 repeat clients
25 years of experience
Stevensville, MD, 21666

Bo is an excellent dogsitter for our three dogs. She comes by twice a week to let our dogs out while we are at work. She is reliable, thorough, communicative, responsible, and so loving to the dogs. We know they are in good hands with her and highly recommend her!

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Leah B.
Sitter Profile Image: Summer B.
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Summer B.
from
$30
per visit
5.0 out of 5 stars
2 reviews
20 years of experience
Wye Mills, MD, 21679

Excellent and thorough! Clearly loves dogs and cats. She was on time and did everything I listed for my pets. The Rover site was easy to use and it gave me quick access to pick Summer as our sitter. Will definitely have her back!

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Mary Ann W.
Sitter Profile Image: Kaileigh T.
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Kaileigh T.
from
$14
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
10 years of experience
Grasonville, MD, 21638

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.!

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Kate M.
Sitter Profile Image: Hannah P.
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Hannah P.
from
$25
per visit
5.0 out of 5 stars
7 reviews
1 repeat client
10 years of experience
Chester, MD, 21619

Thank you Hannah for this trial run. Taking the time to get to know my boys & their schedules We are looking forward to our vacation now knowing they will be well taken care of while we are gone

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Julie B.
Sitter Profile Image: Brooke F.
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Brooke F.
from
$25
per visit
5.0 out of 5 stars
77 reviews
17 repeat clients
10 years of experience
Chester, MD, 21619

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!

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Chrissy L.
Sitter Profile Image: Bryan J.
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Bryan J.
from
$20
per visit
5.0 out of 5 stars
3 reviews
3 repeat clients
20 years of experience
Chester, MD, 21619

Bryan did an excellent job dropping in on our two elderly dogs and my cat 4x a day for three days. I highly recommend him. He followed my instructions with medications for my dogs precisely. Walked and spent time with them all and sent great pictures and reports daily. We are very pleased with Bryan’s outstanding care for our fur babies. I already rebooked with him for future dates.

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Joanna Z.
Sitter Profile Image: Savannah T.
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Savannah T.
from
$30
per visit
5.0 out of 5 stars
10 reviews
4 repeat clients
1 year of experience
Stevensville, MD, 21666

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!

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ruthie b.
Sitter Profile Image: Josiah S.
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Josiah S.
from
$10
per visit
5.0 out of 5 stars
1 review
12 years of experience
Centreville, MD, 21617

About: I will love and take care of your pets as if they were my own. I love to go out and play with pets I care for. I would dog sit when I was in high school for different families. Those families loved how attentive I was, and as a result they would refer me to their friends. I’m always available for you buddies! You and me both know that your pets are more than pets, theyre family. You don’t want just anyone taking care of family. I do currently work full time, however I have a job that is extremely flexible. I set my own hours, including when I am in my office. This pairs perfectly with animal care and house care because I can come and go as frequently as needed. Due to my open schedule I can be available for any needs your pets may have. I prefer to let the client tell me exactly what they want for their pet. I like to keep your life as simple as possible while giving you peace of mind by following any requests you have. If you need your animal crated, if you want them roaming, whatever is asked you can expect to be done.

Sitter Profile Image: Lena M.
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Lena M.
Star Sitter
from
$40
per visit
4.9 out of 5 stars
21 reviews
6 repeat clients
20 years of experience
Stevensville, MD, 21666

Lena was a calm, caring presence for my senior kitty -- just what he needed. I so appreciated her photos and videos as well. Will definitely use her again!

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Laura T.
Sitter Profile Image: Chloe T.
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Chloe T.
from
$32
per visit
4.9 out of 5 stars
12 reviews
2 repeat clients
17 years of experience
Easton, MD, 21601

Chloe was excellent and took great care of our cats! She is very dependable and spent time with them while we were away.

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Allen R.
Sitter Profile Image: Sydney T.
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Sydney T.
from
$30
per visit
5.0 out of 5 stars
9 reviews
6 repeat clients
17 years of experience
Wye Mills, MD, 21679

Sydney met with me and Jojo beforehand and then did a drop-in visit with Jojo. Jojo loved her visit. It was nice knowing I can count on Sydney while I am at work and I received a report card, pictures & a video! Thanks so much!

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Cheryl C.
Sitter Profile Image: Brianne S.
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Brianne S.
from
$25
per visit
4.0 out of 5 stars
4 reviews
1 repeat client
15 years of experience
Chester, MD, 21619

About: Before joining Rover I mainly provided my services through word of mouth. I have experience with providing basic medical care for dogs and cats, and training experience including potty training and easing separation anxiety. I have vast experience and knowledge on various breeds and their specific needs, and really just love being able to have the time and availability to be able to provide these services. They say a dog is a man’s best friend, but in my case, a dog has always been a woman’s best friend! I offer dog sitting, walking, training and boarding at my home as well. I am brand new to the app but I do have plenty of references and want to make all owners feel just as comfortable as I want to ensure their pets will feel with me! I currently work a part-time job from my home, so I have a flexible schedule and able to meet any needs your pet has. I am available everyday, all hours mainly, and can accommodate you and your pets schedule! In my home all pets are welcome. I have plenty of walking trails and a back yard for pets that stay at my home. I typically will customize the walks, food, bathing etc depending on the needs of the pet and what works best for them and the owner.

Sitter Profile Image: Alexis B.
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Alexis B.
from
$16
per visit
5.0 out of 5 stars
1 review
1 repeat client
12 years of experience
Grasonville, MD, 21638

About: I have always been an avid animal lover, and have been an active caretaker in my community. Dogs, cats, fish, you name it. I'm happy to take pets on runs/walks, make sure they get plenty of playtime and love, and treats too. I am mostly available on weekends, and occasionally weekdays, inquire and we can work something out together. But can often stop by to let a pet out during the day. I will follow whatever instructions you have and need for the best care of your animal. I will check in with you if you need me too, and make sure everything is done to your liking.

Sitter Profile Image: Rachel R.
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Rachel R.
from
$20
per visit
8 years of experience
Stevensville, MD, 21666

About: I have been caring for cats and dog since I was a freshman in high school and have pet sat for several families! I have taken care of all different breeds from small to big and young to old! Whether it’s just a quick feed, playtime, administering medicine, or overnight care, I will make sure your pet feels loved, safe, comfortable, and cared for! I currently work at a produce stand working about 5 days a week! My schedule however is extremely flexible as I get to choose the days I want off. I also work with other girls my age that pet sit and we are able to leave when needed to provide care! In my home, we have a nice sized backyard where I am able to play catch and I also live in a large neighborhood where I walk everyday and can exercise with your pet! I also have a clean house if your pet is indoors!

Sitter Profile Image: Cristina M.
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Cristina M.
from
$30
per visit
5.0 out of 5 stars
9 reviews
25 years of experience
Stevensville, MD, 21666

Cristina is an excellent pet sitter! Our sweet kitty is in end stage cancer and Cristina took such great care of her, ensuring she got her shot and monitored her food/water intake to assure us that all was well while we were away. I would definitely hire Cristina again!

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Sue M.
Sitter Profile Image: Jennifer S.
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Jennifer S.
from
$30
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
4 years of experience
Centreville, MD, 21617

About: As a CPDT-KA certified trainer, I offer dog walking services that go beyond basic exercise. Each walk incorporates training and enrichment tailored to your dog’s unique needs. My expertise is ideal for dogs who are fearful, nervous, hyper, or reactive—especially those other walkers may find challenging. A training walk is a perfect way to advance your dog’s progress when your schedule is too packed for regular training sessions. Please note: My walking services are not suitable for aggressive dogs. If you’re dealing with aggression, please contact me directly or explore my specialized training services. I offer training walk services Monday through Friday, with both daytime and evening availability. For the best results, I recommend scheduling two sessions per week, such as Monday/Tuesday or Wednesday/Thursday. I exclusively use positive reinforcement techniques to care for and train dogs, whether during training walks or in your home. My focus is on creating a safe, encouraging environment that builds trust and confidence in your dog. Each session is tailored to meet your dog’s unique needs while reinforcing good behaviors in a kind and effective way. With this approach, I ensure your dog feels supported and thrives in their routine.

Sitter Profile Image: Julie K.
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Julie K.
from
$25
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
5 years of experience
Chester, MD, 21619

She was amazing!! Super flexible with our crazy schedule!

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Jenna K.
Sitter Profile Image: Amanda M.
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Amanda M.
from
$25
per visit
5.0 out of 5 stars
1 review
15 years of experience
Chester, MD, 21619

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

Sitter Profile Image: Kate M.
Verified Background Check
Kate M.
from
$25
per visit
4.8 out of 5 stars
5 reviews
2 repeat clients
32 years of experience
Chester, MD, 21619

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.

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The median cost per visit for cat sitting in Winchester Estates is $22

Cat parents share their Rover experiences - Winchester Estates

1 / 1
5.0 out of 5 stars

Second time that we’ve had Kaileigh check on our kitties! She is extremely reliable and does a great job!

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Kate M.
Drop-In Visits
5.0 out of 5 stars

Fantastic job with taking care of our pets. She took some of the best pictures and kept us thoroughly updated. We would happily use her again.

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Justin A.
Drop-In Visits
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  • 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?

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  • 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 cats like family

  1. 1. Search

    Browse profiles of sitters near you who offer cat sitting
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Popular requests for cat sitting - Winchester Estates

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Sitters in Winchester Estates average 6
repeat cat sitting clients

FAQs for Drop-In Visits - Winchester Estates

Frequently asked questions about Rover

The average cost for Cat Sitting in Winchester Estates on Rover is $15.54 per visit (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Cat 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 Cat Sitting. For more information on service fees, click here .

As of August 2026, there are 1,078 sitters on Rover offering Cat Sitting across Winchester Estates. Enter your ZIP code to see which available sitters are closest to your home.

Cat sitters on Rover care for your cats’ needs and can spend quality time with them, including activities like feeding, playing, and refreshing their water and litter boxes. Depending on your arrangement, you can schedule as many visits per day as your cat needs or find a sitter who can stay at your house overnight. Some sitters also board cats in their home.

House sitting can be ideal for cats who need socialization or care that lasts longer than a few hours. Your cat stays in their own home, on their own schedule, with care based on what you and your sitter agree on together.

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.

A Meet & Greet is a short introductory meeting between you, your cat, 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.

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

  • 92% of sitters can help with special care needs
  • 98% can help with giving oral medications or injections
  • 96% 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.

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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