Cat Sitters in Winchester, MA

Any sitter, one price
$20 per night

Loving sitters near me

Rose
4.98
• 61 reviews
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Rose and mark were fantastic. Very professional and caring sitters. I never felt that I needed to worry about anything. They left my home in the condition as if they had never been there. I, absolutely couldn't have been more impressed and pleased.

Sitter available from Oct 1
Annie
5.00
• 51 reviews
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Annie sat for our cat, Tuna, over a long weekend. She was extremely kind and self-sufficient. When we arrived home, Tuna was relaxed and happy and our apartment was as clean and tidy as we had left it. Annie would be welcome to sit for us again any time, we'd highly recommend her.

Sitter available from Oct 1
Jordan & Nataki
5.00
• 49 reviews
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I could not have asked for a better first experience with zeewoi! Jordan and Nataki were great at communicating from the very start, and they sent me pictures and updates every day. I didn’t have to worry for a moment that my cat Anya was feeling lonely because I could tell she warmed up right away, even though she’s usually quite shy! They also went above and beyond making sure my apartment was tidy for when I got home. So grateful and would definitely be honored for them to sit for me again any time!

Sitter available from Oct 1
Francesco
5.00
• 43 reviews
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Francesco has been taking care of my furry babies and my place while I'm away for well over a year now, and I couldn't appreciate him more. He is a joy to communicate with, and the most reliable person one could hope for. Being able to count on him while I'm traveling makes a world of difference, because I know I don't need to worry about anything while I'm away. Benny and Zumba love him and are very well taken care of. I know because I come home to two very relaxed and happy kitties. I am super grateful to have found Francesco!

Sitter available from Oct 1
Patti
5.00
• 24 reviews
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Everything was great even though they were here for some unfortunate circumstances (hurricane and extended power outage). Sent frequent updates and our cat seemed to like them.

Sitter available from Oct 1
Hannah
4.86
• 28 reviews
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Hannah and Joseph were so kind, so communicative, and clean! Kevin seemed so happy in all the photos they sent. Not only did they wash my sheets and towels they used (without my requesting it, simply out of the kindness of their hearts), they ALSO then put my fresh sheets on the bed! 🥹❤️ Such incredible sitters. 10 stars!

Sitter available from Oct 1
Misti
5.00
• 26 reviews
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Misti was wonderful! She was able to come by before I left town to meet my dog, Grace, which I really appreciated. She sent daily pics or videos and made sure that Grace got tons of snuggle time, which is a major requirement to keep my dog happy :) Cats and skateboards are evil enemies to Grace and it sounds like Misti experienced both and handled it flawlessly! Misti was a great communicator, left everything tidy for me when I got home and Grace was super mellow and relaxed, which tells me she got all the care she needed while I was gone. I highly recommend Misti - I'll definitely be asking her to sit again!

Sitter available from Oct 1
Lilly & Thomas
4.87
• 38 reviews
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Lilly and Thomas stayed at our house and cared for our dogs for a month. I think they took the dogs to the beach nearly every day. Seeing pictures of our dogs on the beach made our time away from them feel so much better. Our house was immaculate when we returned, and we felt so fortunate to have such kind and loving people step in for us in our absence. Anyone would be super lucky to have them in their home.

Sitter available from Oct 1
Gwynn
4.93
• 58 reviews
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Gwynn was wonderful! She was super communicative, flexible to come to our house beforehand to get oriented, and attentive to details. She connected with our pup, Scout, immediately and we felt so assured that he would be well cared for with her. We hope Gwynn can come stay again another time!

Sitter available from Oct 1
Courtenay
5.00
• 18 reviews
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I was thrilled to have Courtenay as our sitter. We had a few last minute changes and she was very accommodating. She is a very pleasant, well spoken person who bonded very quickly with our dog, Pepe. We were in Europe and Courtenay keep us we’ll informed via internet, pictures and all. We came home to a clean house, a happy pet and a delicious pie she left for us in the refrigerator. You would be very pleased to have her as your sitter. Lucy Hottle

Sitter available from Oct 1
Wendy
5.00
• 24 reviews
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Wendy was great, she kept us updated on the dogs and all the fun she had hiking with them on the mountain. I returned home to a very tidy house. My dogs just loved her. I will definitely have Wendy sit for me again and would be very lucky to have her do a sit for you.

Sitter available from Oct 1
Julian & Susan
4.94
• 47 reviews
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Julian and Susan were amazing, we came home to happy healthy creatures and a clean, tidy home and yard. They communicated with us during our vacation, both about anything unusual and just to let us know when things were going well (as they were the majority of the time). They are very adaptable and capable people, I highly recommend them for your home and pet needs.

Sitter available from Oct 1
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Reviews from Cat Owners

4.93
4.93
4.96 Organised 4.96 Reliable 4.95 Clean and tidy 4.97 Self-sufficient 4.91 Pet care
User
Melina
There are not enough words in the English language to express my deepest gratitude to Teresa and all the amazing love and care she showed my sweet cat Milo.

From the moment she met Milo, I knew there was going to be a very special bond. 
He instantly relaxed when he first met and already looked so happy and at peace with her. The bond between the two of them only seemed to get stronger and stronger with every day that I was away.

This two-week trip was so important for me as it was the first real "vacation" I had taken in a few years. I was in desperate need of a mental and physical break and knew that in order to have a true "time off', I needed to feel completely at peace with Milo being well-taken care of.

Well my prayers were answered as Teresa was the "cat whisperer" I was hoping for.

I could not have asked for a better, more compassionate, self-reliant, and intuitive sitter ! 

Teresa was also so diligent in sending me her daily picture and video updates of my cat. With every picture and video I saw, I knew that Milo was so happy being with her and I never worried for one minute while I was away. What a gift !

Teresa was also a serious life-saver for me as literally an hour before I was leaving for my trip, I found out my cat's tracker app was not working and after a few emails and phone calls, we found out the tracker's server was down.

Teresa took the initiative to follow up with getting the tracker to work again which was a HUGE stress-relief for me . She is not only wonderfully savvy with animals but also with technology as well ! 

I feel so fortunate to have Teresa in my life now, not only as an amazing sitter for Milo but also as a wonderful friend for life! 

Thank you, Teresa for everything....

Milo and I so appreciate you .....
User
Meghan
Kristi was an absolutely incredible sitter -- I think our favorite one ever! She was easy to communicate with, kind and personable, and took great care of our pets and our house. It was the first time we had left both our dog and our cat with a TH sitter and Kristi went above and beyond. She was very self-sufficient but provided fun updates and pictures and our pets loved her. Highly recommend!
User
Regina
Hannah and Joseph housesat our three kitties for a week and a half while we were traveling for the holidays. They were very communicative and conscientious. We received daily updated on our cats with cute and funny pictures. When they noticed our 17yo cat, Amber, wasn’t eating very much, they let us know and we were able to resolve the problem quickly. They were also very resourceful and understanding when we ran out of some cat supplies. Hannah and Joseph took great care of the house. Everything was very clean and tidy when we arrived back, and we had a short time to get to know them on our arrival. We would be fortunate to find more house sitters like them, and would of course love to have them back in the future! We wish Hannah and Joseph luck in their travels!
User
Jessica
Kathryn was amazing. She helped me figure plans out after another sitter dropped out at the last minute and saved the day! My cat and fish were well taken care of, and she was super communicative when my tank had a problem child moment. Would definitely recommend her to anyone looking for a reliable, helpful, and caring sitter!!
User
Nina
After seeing the numerous positive reviews, I knew Cung would be an easygoing and professional cat sitter and house guest, and he was :-) Easy communication, prompt updates and clear concern for Boz & Artie's wellbeing, and pictures of cozying up on the couch together all made our time away secure and stress free. Upon returning home, the cats were chill and the apt was left spotless, as though he hadn't even been there.
User
joby
Amanda is truly our trusted sitter "find"!  She comes back regularly, so much so that our kitties think she is their secondary owner!  Always reliable, clean, responsible and most of all loves our cats as much as we do!  Good communicator, self reliant - all in all a perfect "10"!
User
Michele and Hugh
Joi did a wonderful job caring for my two cats and two guinea pigs, as well as caring for my home!  She is coming back in November for a long sit while I am out of the country and we all can’t wait.  Joi had experience with rabbits and jumped right in with guinea pig care.  She is so calm around them that they were sitting on her lap day one!  She spent time preparing their vegetables and kept their enclosure and room clean, which requires daily effort.  She even washed the floor mats in their room so it was fresh when I returned home.  She went above and beyond sending me daily photos and videos so I could see that everyone was healthy and happy.  It was apparent to me that she spent a lot of time with my pets, which is very important so they don’t become stressed and lonely when I am away.  Joi also took excellent care of my two cats.  They receive daily wet food with some medication and she ensured that they received it on time.  My cats barely noticed when I returned because they got so much attention from Joi.  She took excellent care of my front garden flowers and my tomato and herb hydroponic gardens.  These take some daily attention and time in the summer, and I returned home to them looking great!  Joi is a very caring, clean, and thoughtful sitter and I hope she comes back many more times!
User
Nancy
Kathy and Ron arrived at our home with a most fantastical toy for our cats and a giant apple pie. Need I say more? They are very experienced sitters and brought personal items that they prefer. We knew we were leaving out cats in good hands. 

A large part of their 'job' was hand watering our garden and Ron took that in stride. Everything is thriving. 

Our cats are usually distant with new people but we received photos of them keeping Kathy and Ron company in various situations which was reassuring. They clearly won our cats over. 

Although Ron and Kathy had a ferry to catch on their last day, they took time to wash  their linens and hang them on the clothesline. They also left us a gorgeous plant for our garden. 

We would very much like to have them back for a longer sit if possible.
User
Christine
Kimberly was absolutely wonderful, and we couldn't have had a better sitter for our first experience with zeewoi. Marshmallow loved Kimberly instantly and our cats (who can be a little standoffish) opened up right away with her. She asked great questions that helped us tailor our Welcome Guide to make sure we could be good hosts. Thank you, Kimberly!
User
Bridget
Lindsey watched our cat and dog for a long weekend when we went out of town. She was a very communicative sitter sending frequent pictures and voice notes with updates. She did a great job of following their schedules and giving them attention. The animals seemed to be happy and relaxed when we returned home and I believe Lindsey enjoyed getting to discover all of the eateries our town has to offer. A win-win for everyone!

Cat Sitting FAQs

Veterinarians advising to leave cats at home with a pet sitter who will stay overnight in your home, boarding is not recommended for cats as they are stressed in a new environment, you can find a sitter who will care for your cats and home overnight at Sittsy.

At least $20 per visit, per overnight watching in your home, otherwise you can find a free sitter at Sittsy.

Inviting a cat sitter to your home, boarding the cat with a local business, asking a friend, family or neighbour to feed and check the well-being. The most efficient way to leave your cat during your vacation is with Sittsy cat sitters overnight, in this way, you will save cat sitting costs and make vacation not only for you but also for your cat sitter!

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