Cat Sitting Winchester

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Over 1
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.

1 / 1
Sitter Profile Image: Katie O.
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Katie O.
Star Sitter
from
$40
per visit
5.0 out of 5 stars
22 reviews
3 repeat clients
20 years of experience
Torrington, CT, 06790

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.

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

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.
Sitter Profile Image: Ashley A.
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Ashley A.
from
$20
per visit
4.9 out of 5 stars
39 reviews
9 repeat clients
10 years of experience
Canaan, CT, 06031

Ashley did such a fabulous job watching our kitties when we were out of town. She even extended an extra couple of days when we were delayed. 10/10 recommend!

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Anna C.
Sitter Profile Image: Elle R.
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Elle R.
from
$14
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
4 years of experience
Torrington, CT, 06790

About: I love being with animals and have experience caring for a wide range of pets, including dogs, cats, jumping spiders, and lizards. I enjoy learning each animal’s personality and making sure they’re comfortable and well cared for. I am a student who goes to college out of state but is home for the month of January and is also working part time. Since losing a dog of my own I figured this would be a great opportunity to help others with their pets and still have a great time with animals. I do have a fenced in yard if I take dogs into my home but in other peoples homes, listening to the guardian is most important to me on how they coexist with their pet and respecting that. At the end of the day I want to help people care for their pets.

Sitter Profile Image: Karina & Jared S.
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Karina & Jared S.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
138 reviews
62 repeat clients
23 years of experience
Barkhamsted, CT, 06063

Karina has been a wonderful caregiver to Dex! She goes above and beyond for him. She thinks of everything and makes sure he is always well taken care of. I have found her to be very reliable and professional and would recommend her to anyone! She is very thoughtful and thorough in all that she does, 5 stars!

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Brianna S.
Sitter Profile Image: Priscilla E.
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Priscilla E.
from
$20
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: Katherine C.
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Katherine C.
from
$50
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: Alexandrine W.
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Alexandrine W.
from
$25
per visit
5.0 out of 5 stars
2 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: Lynsey M.
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Lynsey M.
from
$30
per visit
5.0 out of 5 stars
27 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: Angela W.
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Angela W.
from
$30
per visit
5.0 out of 5 stars
117 reviews
45 repeat clients
15 years of experience
Torrington, CT, 06790

Angela is a reliable and caring pet lover. She is super flexible and very knowledgeable when it comes to the well being of like dog. We appreciate all the tips she has given us for our puppy. We will be using Angela again soon

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Amy R.
Sitter Profile Image: Laina W.
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Laina W.
from
$25
per visit
4.7 out of 5 stars
11 reviews
1 repeat client
18 years of experience
Central East Denver, Harwinton, CT, 06791

Laina was amazing. She came in the heat of a very hot day and took our dog out while we were gone for the evening. She was timely with responses and very friendly. Communication was a breeze. Will definitely use her again!

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Kyle F.
Sitter Profile Image: Maren P.
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Maren P.
from
$14
per visit
5.0 out of 5 stars
1 review
1 year of experience
Simsbury, CT, 06089

We needed someone to check in on our pups last minute and Maren came to our rescue! Will definitely hire her again!

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Miranda D.
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

This is the first time I’ve used Rover and I couldn’t be more pleased with Ashley E., who recently cared for our 2 male doggies, while we threw a wedding for our daughter. We have a 6 yr old Belgian Shepherd and a 13 yr old Westie. Ashley was wonderful with each of them giving equal love and attention according to their energy and needs level and all the while keeping me calm by sending texts and photos each time she visited. When she came to meet our dogs, our Belgian actually kissed her, which he rarely does with us! Our Westie requires much medication which she made sure to clearly understand and administer, that was one of my biggest worries about hiring a pet sitter and she did it with ease. Most impressive to me was the morning of the wedding my husband was alone to get ready and needed help with his bowtie, cufflinks and button covers of his shirt. Ashley rescued all of us by helping him, THANK YOU!!! That was above and beyond the call of duty, ha ha. I will definitely be using Rover again and definitely Ashley E!

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Karen K.
Sitter Profile Image: Amanda O.
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Amanda O.
from
$25
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: Melanie D.
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Melanie D.
from
$20
per visit
5.0 out of 5 stars
12 reviews
5 repeat clients
14 years of experience
Southwick, MA, 01077

This is the second time we had Melanie take care of our four cats - she gets a 16 (out of 16) paws up from the 4 cats! We came home to very clean food bowls and litter boxes. Food was also left organized! She had great communication. She even accommodated a special diet and feeding cats in two locations. Will use again! Top ratings for Melanie!

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Simone B.
Sitter Profile Image: Zachary N.
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Zachary N.
from
$20
per visit
3 years of experience
Torrington, CT, 06790

About: I have had dogs my whole life but 2 of my dogs gave birth to 11 puppies in October of 2022 and I helped take care of them all until they were ready to go to their new homes. I kept one of the puppies and have taken care of her since she was a newborn so I am very familiar around all types of dogs. I’m currently available most weekdays and weekends. I keep my calendar up to date and do my best to accommodate last-minute requests whenever possible. Feel free to reach out with your dates, and I’ll respond as quickly as I can. I will make sure your pets are getting enough attention and exercise when you are away and will treat them like they are my own.

Sitter Profile Image: Aaliyah R.
Verified Enhanced Background Check
Aaliyah R.
from
$14
per visit
22 years of experience
Northfield, CT, 06778

About: Ive had pets my whole life, from reptiles to birds to our furry friends. Ive done it all! Loving and caring for animals is one of my greatest passions, Ive been taught from a very young age to treat our lovely companions with the greatest kindness and respect. As a college student ill be able to take care of your pets before and after my classes! I of course can discuss details when booking! I am very detail oriented when it comes to our companions, I will adjust to the schedule you have set for them! As a pet owner i understand the importance of keeping your pets comfortable and happy.

Sitter Profile Image: Alexis G.
Verified Background Check
Alexis G.
from
$57
per visit
5.0 out of 5 stars
6 reviews
2 repeat clients
36 years of experience
Avon, CT, 06001

About: Taken care of different breeds, small and big dogs, cats and small critters. Trained dogs used for disabilities. I walk small dogs with a harness only, and don’t allow them to jump from high places, due to their tiny bones. I make sure they are secured before opening any door where they might run off. I have an Instagram page where I upload dogs I meet , dogs I take care of or watch , dogs that were placed in safe homes. I will take photos to give updates. Can change day to day but if notified ahead of time , can usually work around my schedule. I do check my texts and email if something changes. My dogs are sociable, always keeping an eye out, they are like little kids. There is currently a Japanese Chin, Shitzu, Pekingese, Saint Bernard, a cat, a bird and 3 guinea pigs, in the home.

Sitter Profile Image: Taylor B.
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Taylor B.
from
$20
per visit
10 years of experience
New Hartford, CT, 06057

About: I have taken care of pets since I was a little girl. I have had two long term jobs at different dog kennels. Which then resulted in me being able to acquire multiple pet sitting jobs. I have experience in pet sitting, dog walking, dog daycare, and some dog training! I am currently a stay at home mom. Both of my children will be starting school soon and I would love to get back into doing what I love with pets! I will make sure to spend as much time with your pet as you desire. Making sure they get all the love,food,treats and playtime they need to make everyone happy!

Sitter Profile Image: Michelle R.
Verified Enhanced Background Check
Michelle R.
from
$45
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

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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
1 / 1
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Popular requests for cat sitting - Winchester

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Sitters in Winchester average 6
repeat cat sitting clients

FAQs for Drop-In Visits - Winchester

Frequently asked questions about Rover

The average cost for Cat Sitting in Winchester on Rover is $18.19 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 802 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:

  • 97% 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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