Pet Sitting in Winchester

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Winchester pet sitters

Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

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Sitter Profile Image: Cheryl R.
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Cheryl R.
Star Sitter
$28
total per visit
5.0 out of 5 stars
552 reviews
108 repeat clients
20 years of experience
Woburn, MA, 01801

This is out second booking with Cheryl, this time for a full week of visits, and she was excellent! She treats my pets like her own and genuinely cares for them. We received plenty of pictures and detailed updates after each visit. My family and I definitely could sleep easier being away from our pets knowing they were in her great care!

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Billy P.
Sitter Profile Image: Erin F.
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Erin F.
Star Sitter
$28
total per visit
5.0 out of 5 stars
159 reviews
56 repeat clients
9 years of experience
Woburn, MA, 01801

There’s no one better than Erin! We’re grateful to her for another great booking, particularly when we had to travel last minute. We always come home to a happy pup!

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Rachel N.
Sitter Profile Image: Jolene G.
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Jolene G.
Star Sitter
$23
total per visit
5.0 out of 5 stars
21 reviews
7 repeat clients
4 years of experience
Winchester, MA, 01890

Thank you, Jolene, for checking in on my two cats over a holiday weekend with a last minute booking! Jolene’s communication and timing was excellent. While checking on the cats, she filled their bowls, gave them treats, and brushed them. I appreciated her time and attention!

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Emily G.
Sitter Profile Image: James T.
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James T.
Star Sitter
$34
total per visit
5.0 out of 5 stars
97 reviews
37 repeat clients
10 years of experience
Stoneham, MA

James is the best!!! Very communicative, provides full run through of activities and behaviors during the visit. He is very loving to the dogs and takes lots of photos and videos! Will 100% book again.

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Diandra L.
Sitter Profile Image: Michael D.
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Michael D.
$28
total per visit
4.9 out of 5 stars
39 reviews
15 repeat clients
30 years of experience
Winchester, MA, 01890

Michael was very communicative and flexible and great with our pup! He's a dog person through and through. Thanks for everything, Michael!

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Jane C.
Sitter Profile Image: Shawn V.
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Shawn V.
Star Sitter
$28
total per visit
5.0 out of 5 stars
129 reviews
43 repeat clients
20 years of experience
Arlington, MA, 02474

We have been using Shawn for over 6 months for weekday drop-in visits with a very elderly dog. Shawn has been 100% reliable and a total pro the one time that the dog became very ill while home alone in the morning. Shawn invented a new outside game for our 13-yr-old pup, and now the dog wants to play the Shawn game anytime we are in the yard. We feel extremely fortunate to have found Shawn on Rover…she gives us total peace of mind that our wonderful dog is well-cared for. Shawn is completely trustworthy and totally dedicated to the well-being of our pet.

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Carolyn R.
Sitter Profile Image: Angela R.
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Angela R.
Star Sitter
$28
total per visit
5.0 out of 5 stars
119 reviews
45 repeat clients
25 years of experience
Stoneham, MA, 02180

Angela has watched my cat Mason twice while I've been out of the country and she put my mind at ease! She sends lovely pictures and updates about him and when I get home, he's very calm and relaxed, rather than stressed from my being away. I'd recommend Angela to any cat parents!

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Beth K.
Sitter Profile Image: Caroline J.
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Caroline J.
Star Sitter
$23
total per visit
5.0 out of 5 stars
28 reviews
9 repeat clients
20 years of experience
Arlington, MA, 02474

Caroline did a great job checking in on my cat while I was away on vacation. She kept everything neat and tidy, paid attention to detail, and was fast/prompt with any communication. Would definitely recommend and will rebook if needed in the future.

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Stephan S.
Sitter Profile Image: Olivia A.
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Olivia A.
Star Sitter
$23
total per visit
5.0 out of 5 stars
9 reviews
4 repeat clients
25 years of experience
Woburn, MA, 01801

Best dog sitter I used 😊

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Hernan C.
Sitter Profile Image: Charlotte C.
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Charlotte C.
Star Sitter
$25
total per visit
5.0 out of 5 stars
89 reviews
28 repeat clients
15 years of experience
Medford, MA, 02155

Charlotte was amazing! She took such great care of our kitties while we were away. We loved her photos and daily updates. She was super easy to communicate with and our nervous cat loved her! I highly recommend Charlotte and will definitely hire her again!

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Katie and Daniel S.
Sitter Profile Image: Maude G.
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Maude G.
$20
total per visit
5.0 out of 5 stars
15 reviews
2 repeat clients
15 years of experience
Stoneham, MA, 02180

Maude has fantastic communication and attention to detail!

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Ripley D.
Sitter Profile Image: Jessica Z.
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Jessica Z.
Star Sitter
$23
total per visit
5.0 out of 5 stars
205 reviews
63 repeat clients
30 years of experience
Arlington, MA, 02474

Jessica is reliable and responsive, and takes great care of my kitty. I will continue to ask her to take care of Rocco every time I go out of town. Thank you Jessica!

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Michelle L.
Sitter Profile Image: Elisangela L.
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Elisangela L.
Star Sitter
$30
total per visit
5.0 out of 5 stars
118 reviews
42 repeat clients
8 years of experience
Woburn, MA, 01801

Elisangela and her girls were amazing! She took great care of our sweet cat Rudy when we were away for a long weekend. She was highly communicative throughout the entire process and left us feeling totally at ease that our guy was in great hands. We would recommend her and rebook with absolutely no hesitation!

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Alison C.
Sitter Profile Image: Sanela F.
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Sanela F.
Star Sitter
$29
total per visit
5.0 out of 5 stars
23 reviews
6 repeat clients
30 years of experience
Stoneham, MA, 02180

Sanela is a very responsive cat sitter and goes above and beyond. Our cat seemed ok at initial meeting but for the second visit our cat Beans was mean toward Sanela. It’s unfortunate but cats are cats, Sanela still stayed and gave her treats and shared photos.

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Meghan Z.
Sitter Profile Image: Yesika S.
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Yesika S.
Star Sitter
$34
total per visit
5.0 out of 5 stars
545 reviews
162 repeat clients
14 years of experience
Medford, MA, 02155

As always, Yesika is my go to person whenever i’m traveling. Very reliable. I love working with Yesika! Also she sent me cute photos of my cat and i often made them as a wall paper on my phone 🥰

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Young-Eun L.
Sitter Profile Image: Cierra K.
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Cierra K.
$17
total per visit
5.0 out of 5 stars
2 reviews
3 repeat clients
17 years of experience
Medford, MA, 02155

About: What sets me apart from other sitters is my deep compassion, patience, and experience with dogs who need extra attention—especially those with anxiety or special routines. I have hands-on experience caring for senior dogs, puppies, and pets who struggle with separation anxiety. My own dog, Sasha, has anxiety, so I understand the importance of gentle care, consistency, and emotional support. I treat every pet like family, and I’m committed to creating a calm, safe, and loving environment while you’re away. Whether your pup needs long walks, slow introductions, or just a cozy lap to nap on—I’ve got you covered! Pet care fits naturally into my weekly routine. I have Mondays and Tuesdays off, which gives me plenty of time for daytime walks and drop-ins. On other days, I’m able to fit in visits between school and work—and I don’t mind doing late-night drop-ins if your pet needs evening attention. Caring for animals is something I truly enjoy, so I’m happy to make it a priority in my schedule. I’m dependable, flexible, and always focused on making pets feel safe and loved while you’re away. I only offer pet care in the client’s home because I believe pets are happiest and most comfortable in their own familiar environment. I follow your pet’s routine closely—whether that’s feeding, walks, playtime, or administering medication. I respect your space, keep things tidy, and make sure your pet feels safe, loved, and cared for while you’re away. My goal is always to provide reliable, stress-free care that gives both you and your pet peace of mind.

Sitter Profile Image: Carmen K.
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Carmen K.
Star Sitter
$19
total per visit
5.0 out of 5 stars
8 reviews
3 repeat clients
4 years of experience
Winchester, MA, 01890

Happy happy dogs!

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Karen B.
Sitter Profile Image: Justin H.
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Justin H.
Star Sitter
$15
total per visit
5.0 out of 5 stars
9 reviews
5 repeat clients
4 years of experience
Stoneham, MA, 02180

About: For the past few years now I’ve been a dog sitter for my family and friends, walking, playing, feeding, and cleaning up after them I can house sit, dog walk, and do drop in visits, Any time of the day Mondays to Fridays, And weekends if needed anything works. I get to learn pets usually routine. How many times a day to walk them, when and how to feed them, and their bed time.

Sitter Profile Image: Noila A.
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Noila A.
Star Sitter
$26
total per visit
5.0 out of 5 stars
7 reviews
2 repeat clients
20 years of experience
Stoneham, MA, 02180

About: Hi! 😊 I have always loved being around animals, and I have spent most of my life around them. I also look after my family and friends pets when they travel. I am flexible on timing and would love to check in on your cats or pups while you are away any time visit is needed. 🥰 Pets need usual routine and I’d provide everything they need to feel safe and loved, including walks, playtime and rest to reduce stress. I love taking photos of our fun moments, and would gladly share with you! ♥️

Sitter Profile Image: Jillian S.
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Jillian S.
Star Sitter
$28
total per visit
5.0 out of 5 stars
30 reviews
8 repeat clients
20 years of experience
Stoneham, MA, 02180

Jillian is wonderful and I will continue to have her taking care of my little guy!!

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Brian S.
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Over 30
pet parents in Winchester have booked pet sitting

Winchester pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Shawn handled everything responsibly and was flexible in accommodating our requests. We were so happy that she got along well with our cat. Thanks for always sending such cute photos!

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

We recently moved to a new apt and needed a new sitter for our 10 year old kitty. Carol did a great job with her in all ways. Carol kept her routine and spoiled her the way we do. Our cat was relaxed and well taken care of by Carol. Highly recommend her pet services.

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Linda K.
Drop-In Visits
5.0 out of 5 stars

Angela was awesome and took lots of photos of our cats! We are very glad to have had her catsit for us

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Lily P.
Drop-In Visits
5.0 out of 5 stars

We love having Cheryl watch our cat when we're away. We know she's in great hands and don't have to worry for a moment. Cheryl is so good with our cat and reading her needs.

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

We use Eunae whenever we’re away and she’s available. Our cats absolutely love her. She’s reliable and always takes a lot of care with our cats, making sure to give them extra love, attention, and playtime. And of course keep them fed and with clean litter.

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Nicole F.
Drop-In Visits
5.0 out of 5 stars

Charlotte was great! Our normal catsitter fell through just a few days before we left for a week, and Charlotte was able to help us out in a pinch. She was responsive, communicative, and took care of everything requested.

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J K.
Drop-In Visits
5.0 out of 5 stars

Another round of petsitting with Maria, another well-loved and cared for pet who was relaxing without a care in the world when we returned! And we were supplied with lovely updates and photos for every check-in. Excellent work!

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Daisy B.
Drop-In Visits
5.0 out of 5 stars

Sharon is wonderful with our cat! She is reliable and kind! We have had the good fortune of booking her multiple times and we hope to book her again the next time we're away!

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Sarah H.
Drop-In Visits
5.0 out of 5 stars

Andrew was great. He was able to take care of my pet needs without a lot of notice. He was communicative and professional.

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Bradley H.
Drop-In Visits
5.0 out of 5 stars

Sanela was amazing! We have a super high energy young cat that needs a lot of play and she did an excellent job in playing with him until he was out of energy. She also did a great job with our older kitty who is all about his special morning soup! We are so happy we picked her and despite the older one not liking many people, he loved being around her immediately. And, even would pose for their daily photo shoot with her, they love her! She is a cat whisperer and we would 110% book again. She also has very reasonable prices for services which is great for our longer trips. And, very respectful of our house rules which is appreciated. Thank you, Sanela! The kitties thank you, too!

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Jetta R.
Drop-In Visits
5.0 out of 5 stars

Bonnie took great care of our cats. She sent lots of good photos and kept us updated throughout our trip.

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

Andrea was great with our cats! She was very patient and accommodating to their different needs. Communication was always clear and timely. She got lots of cute photos of them for us too!

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Matthew C.
Drop-In Visits
5.0 out of 5 stars

My cats, Taz and Luca, loved Allie. This was our first time using Rover, and I wasn't sure how Luca would react — but he surprised us. He was comfortable and even enjoyed playtime. Allie is responsive and easy to communicate with, and I knew my cats were in good hands. Highly recommend!

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Karen S.
Drop-In Visits
5.0 out of 5 stars

Sasha helped us out with a last minute booking and was very communicative. She even got our very shy cat to come out from hiding and we came back to a happy girl. We would definitely book with Sasha again!

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Kerry J.
Drop-In Visits
5.0 out of 5 stars

Anneke was amazing! Very communicative, sent lots of pictures and detailed updates. We will definitely book with her again.

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

This is my second time booking Max and he has once again done a really wonderful job caring for my cat while I was gone.

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Simon K.
Drop-In Visits
5.0 out of 5 stars

Blane was great with our cat and our apartment, everything was done to our cat’s liking, and he was happy and well-fed when we returned! Blane was very easy to work with, responsible, and in the future I hope he’s avalible to stop in for Salem again!

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Asa B.
Drop-In Visits
5.0 out of 5 stars

Alix was a great cat sitter for my 2 cats- very diligent about care and instructions. I would definitely rebook.

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Jennifer F.
Drop-In Visits
5.0 out of 5 stars

Caitlin is our go to cat co-parent! She’s so good with our Titus and we feel a little less guilty when we’re away knowing that she’s coming to spend time with him.

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Anthony C.
Drop-In Visits
5.0 out of 5 stars

Oli was wonderful - my kitties were so happy to have someone to hang out with. And I was happy to get such wonderful updates and pictures!

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Chelsea K.
Drop-In Visits
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Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for pet sitting in Winchester is $25

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 pet 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.

Sitters in Winchester average 6
repeat pet sitting clients

Pet Sitting FAQs

Frequently asked questions about Rover

Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Winchester on Rover as of Jun 2026 was about $25 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.

If you’re searching for a Winchester pet sitter for the first time, visit the pet sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a pet sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 10,555 pet sitters in Winchester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.

Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 86% of Winchester pet sitters respond in under an hour.

Pet sitters in Winchester have an average of 14 years of experience. Pet sitters with repeat customers have an average of 6 repeat clients. Experience can vary from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Winchester.

Rover makes it easy to find Winchester pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:

  • Pets of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Pets who’d love to socialize with their pet sitter’s pets

There are 10,555 pet sitters in Winchester on Rover, so you’re sure to find the perfect match for your pet! In Winchester, 95% of pet sitters offer daily exercise, 95% offer medication administration, and 90% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass background checks for you and your pet’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your pet sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.