Cat Sitting Winchester

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pet parents in Winchester have booked cat sitting

Winchester, 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: Isabelle R.
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Isabelle R.
from
$14
per visit
5.0 out of 5 stars
• 4 reviews
1 repeat client
6 years of experience
Winchester, CT, 06098

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.

Sitter Profile Image: Stacey G.
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Stacey G.
from
$30
per visit
5.0 out of 5 stars
• 33 reviews
7 repeat clients
15 years of experience
Winsted, CT, 06098

“Stacey was great. She even managed to get my very shy cat to come out from her hiding spot. I would definitely have Stacey take care of my Cat again”

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James C.
Sitter Profile Image: Alexandrine W.
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Alexandrine W.
from
$25
per visit
5.0 out of 5 stars
• 3 reviews
1 repeat client
18 years of experience
Winchester, CT, 06098

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!

Sitter Profile Image: Ashley A.
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Ashley A.
from
$18
per visit
4.9 out of 5 stars
• 44 reviews
9 repeat clients
10 years of experience
Canaan, CT, 06031

“Ashley took amazing care of our two kitties while we were on our honeymoon. We were able to have a stress-free trip knowing we could count on her to be there twice a day to feed them AND spend time with them! I will definitely be booking Ashley next time we go away, and you should too! She’s very sweet and intentional with animals. ❤️”

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Rachel B.
Sitter Profile Image: Lynsey M.
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Lynsey M.
from
$27
per visit
5.0 out of 5 stars
• 28 reviews
11 repeat clients
8 years of experience
Torrington, CT, 06790

“Lynsey is absolutely phenomenal! She took fabulous care of our wonderful cat, Inga, who is often shy with new people. Lynsey made Inga feel comfortable immediately and this continued for the entire time we were away. Lynsey was reliable, communicative, and it was a true privilege to work with her. We'd give her ten stars if we could, and cannot.say enough good things about her.”

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Christina B.
Sitter Profile Image: Tara N.
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Tara N.
from
$23
per visit
5.0 out of 5 stars
• 31 reviews
13 repeat clients
25 years of experience
Torrington, CT, 06790

“My husband and I knew upon meeting Tara for the first time that she was the perfect fit with our cat, Charlie. Charlie is very shy and usually hides when people come to visit. However, this was not the case when Tara entered our home. Tara did a top-notch job taking care of Charlie during her drop in visits over a period of one month. We were so happy when she sent up pictures and updates. Tara is reliable, kind, professional, and a true animal lover. Cats can be messy with the litter, etc. But with Tara on the job, we came home to a very neat home and well-fed, content cat. We will definitely seek Tara services again. Furthermore, we highly recommend her. Thanks a million, Tara.”

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Claudia W.
Sitter Profile Image: Karina & Jared S.
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Karina & Jared S.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 142 reviews
63 repeat clients
23 years of experience
Barkhamsted, CT, 06063

“This is the third time that Jared has taken care of my cat while we were away. Once again, excellent care and service. Reliable and attentive. He did everything I asked. I will be booking Karina and Jared again later this summer!”

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Bridget S.
Sitter Profile Image: Marisa M.
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Marisa M.
from
$25
per visit
5.0 out of 5 stars
• 33 reviews
11 repeat clients
16 years of experience
Torrington, CT, 06790

“Marisa stayed at our house for more than two weeks, caring for our cat and plants. She did an exceptional job! Our cat was very content and hardly seemed to miss us, which really shows how comfortable she was with Marisa. I would recommend her to anyone, and we would be delighted to have her house sit for us again!”

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Marina Y.
Sitter Profile Image: Morgan D.
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Morgan D.
from
$15
per visit
5 years of experience
torrington, CT, 06790

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!

Sitter Profile Image: Sara C.
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Sara C.
from
$14
per visit
10 years of experience
Harwinton, CT, 06791

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.

Sitter Profile Image: Ashley E.
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Ashley E.
from
$30
per visit
5.0 out of 5 stars
• 50 reviews
10 repeat clients
28 years of experience
Torrington, CT, 06790

“Ashley was great- communicative, extremely helpful, and managed all the cat care throughout blizzard conditions! My cat was totally relaxed and happy when we came home. Thank you Ashley!”

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Corey L.
Sitter Profile Image: Katie O.
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Katie O.
from
$36
per visit
5.0 out of 5 stars
• 23 reviews
3 repeat clients
20 years of experience
Torrington, CT, 06790

“Wow! We’ve had several sitters over the years and Katie was BY FAR the best sitter ever! We booked the house sitting option and Katie was able to let our kitties out for even longer than expected. She went above and beyond. She let us know when food was running low and even offered to go get it!! Constantly sent us awesome photos and really seemed to bond with our furry babies.”

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Angela M.
Sitter Profile Image: Michelle R.
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Michelle R.
from
$18
per visit
5.0 out of 5 stars
• 1 review
1 repeat client
28 years of experience
Winstead, CT, 06098

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

Sitter Profile Image: Laina W.
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Laina W.
from
$35
per visit
4.7 out of 5 stars
• 11 reviews
1 repeat client
18 years of experience
Central East Denver, Harwinton, CT, 06791

“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!!”

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Felicity F.
Sitter Profile Image: Priscilla E.
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Priscilla E.
from
$18
per visit
5.0 out of 5 stars
• 13 reviews
2 repeat clients
20 years of experience
New Hartford, CT, 06057

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.

Sitter Profile Image: Amanda O.
Verified Enhanced Background Check
Amanda O.
from
$23
per visit
5.0 out of 5 stars
• 8 reviews
10 years of experience
Barkhamsted, CT, 06063

“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.”

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Jessica P.
Sitter Profile Image: Meaghan G.
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Meaghan G.
from
$22
per visit
5.0 out of 5 stars
• 19 reviews
8 repeat clients
10 years of experience
Harwinton, CT, 06791

“Meaghan was wonderful with our kitties. She made sure they were taken care of even with a storm she was on time and helpful with prompt communication. So grateful to find her!”

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Joy P.
Sitter Profile Image: Katherine C.
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Katherine C.
from
$45
per visit
5.0 out of 5 stars
• 16 reviews
3 repeat clients
10 years of experience
Torrington, CT, 06790

“Katie took such good care of my kitties! She stopped in prior to our scheduled pet sitting to meet my cats, which was much appreciated. She did everything I asked, and made an effort to give my kitties some playtime, even though they were being shy. She provided lots of pics and feedback after each visit, which I love to see, as I worry about my girls when I can’t be home with them. We will definitely be using her services again! ?”

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Natalie C.
Sitter Profile Image: Elissa U.
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Elissa U.
from
$26
per visit
5.0 out of 5 stars
• 6 reviews
9 years of experience
Canton, CT, 06019

“I really appreciate the time and attention she gave to my cat, Joy, while I was away.”

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Walt T.
Sitter Profile Image: Jaylese H.
Verified Enhanced Background Check
Jaylese H.
from
$23
per visit
5.0 out of 5 stars
• 32 reviews
11 repeat clients
6 years of experience
Plymouth, CT, 06786

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.

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The median cost per visit for cat sitting in Winchester is $25

Cat parents share their Rover experiences - Winchester

1 / 1
5.0 out of 5 stars

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!

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Susan H.
Drop-In Visits
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Sitters in Winchester average 6
repeat cat sitting clients

FAQs for Cat Sitting - Winchester

Frequently asked questions about Rover

The average cost for Cat Sitting in Winchester on Rover is $18.19 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 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 September 2026, there are 803 sitters on Rover offering Cat Sitting across Winchester. 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. On Rover:

  • 98% of sitters can help with special care needs
  • 95% can help with giving oral medications or injections
  • 98% 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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