Cat Sitting Winchester

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Over 55
pet parents in Winchester have booked cat sitting

Winchester, Find top rated cat sitting

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

1 / 1
Sitter Profile Image: Elizabeth R.
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Elizabeth R.
Star Sitter
$20
total per visit
4.9 out of 5 stars
• 14 reviews
11 repeat clients
20 years of experience
Woburn, MA, 01801

“Elizabeth was EXCELLENT! My cat liked her from day one. I will for sure be requesting her again. She was so friendly and detailed.”

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Joy T.
Sitter Profile Image: Jolene G.
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Jolene G.
Star Sitter
$17
total per visit
5.0 out of 5 stars
• 31 reviews
7 repeat clients
5 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: Angela R.
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Angela R.
Star Sitter
$28
total per visit
5.0 out of 5 stars
• 153 reviews
56 repeat clients
25 years of experience
Medford, MA, 02155

“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: Olha P.
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Olha P.
Star Sitter
$28
total per visit
5.0 out of 5 stars
• 27 reviews
7 repeat clients
2 years of experience
Melrose, MA, 02176

“Olha is such a wonderful sitter! She took a great care of our cat Leo and is very patient and attentive to Leo’s needs. Would highly recommend!!”

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Cecilia F.
Sitter Profile Image: Sasha P.
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Sasha P.
Star Sitter
$26
total per visit
5.0 out of 5 stars
• 59 reviews
19 repeat clients
25 years of experience
Cambridge, MA, 02140

“Sasha is great! She took amazing care of our two kitties while we were away for almost two weeks. Communication was excellent; she sent little updates and pictures every day. Thank you, Sasha!”

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Robyn S.
Sitter Profile Image: Julianna D.
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Julianna D.
$26
total per visit
5.0 out of 5 stars
• 5 reviews
1 repeat client
15 years of experience
Somerville, MA, 02143

“Julianna did a great job, playing with our cat and sending lots of cute photos. We are going to use her again very soon.”

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Michael N.
Sitter Profile Image: Hillary C.
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Hillary C.
$26
total per visit
5.0 out of 5 stars
• 16 reviews
4 repeat clients
13 years of experience
Arlington, MA, 02474

“Hillary was so great! Chloë loved her and I felt so reassured knowing she was well-cared for. Hillary spent quality time with Chloë and sent lovely, detailed notes and photos. Highly recommend!”

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Suzanna C.
Sitter Profile Image: Justin H.
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Justin H.
$14
total per visit
4.8 out of 5 stars
• 17 reviews
14 repeat clients
4 years of experience
Stoneham, MA, 02180

“Justin was great with our 2 senior whippets. He is prompt and reliable. We definitely recommend him for your pet’s needs!”

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Monique P.
Sitter Profile Image: Rachel V.
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Rachel V.
$18
total per visit
1 repeat client
3 years of experience
Somerville, MA, 02144

About: My kids and I are big dog lovers and would love to help care for your furry family members! 🐾 We’re excited to offer dog walking services in the area and have experience with both dog and cat sitting. We understand how important it is to know your pets are in caring, loving hands, and we’ll treat your pets like part of our own family! I work part-time remotely, which gives me a flexible schedule and plenty of opportunities to spend time with your pets! I’m available for walks, playtime, or simply keeping your dog company during the day and early evenings. I live in a 3 bedroom condo in Somerville and have a great, quiet neighborhood and live near several parks. There is ample space for your pet to be comfortable and get exercise.

Sitter Profile Image: Owen H.
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Owen H.
$18
total per visit
2 repeat clients
15 years of experience
Somerville, MA, 02144

About: I have walked dogs since I was 7 years old, starting with my family’s yellow Lab Phoebe, taking on neighbors as clients. I have since enjoyed pet-sitting for friends and having my own pets, including my darling cat Caramel. I have a very flexible schedule as a graduate student — outside of class I am typically at home or studying close by, often in pet-friendly and outdoor spaces where I would love to have your pet join me. I love a long walk and will walk your dog as far as you would like! I am empathetic and considerate and have a deep respect for pets and the humans they live with. I am a clear communicator and will always do my utmost to understand your pet’s needs and give them excellent care.

Sitter Profile Image: Hassan A.
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Hassan A.
$18
total per visit
7 years of experience
Woburn, MA, 01801

About: I personally love animals and I’ve been taking care of pets since I was around 10-11 years old. I have the most experience with cats and rabbits and fish as I’ve owned a lot of them. Although I’ve never owned one I am well experienced with dogs too as I volunteered at an adoption center and have taken care of my friends dogs many times. I have also worked with birds, hamsters, gerbils, snakes, turtles, frogs, lizards, and farm animals. I am an 19 year old college student and I’m really excited for this opportunity to make some extra money doing what I love. I’m currently working part time and I only go to school 2 days a week, leaving me with plenty of time to take care of your pet. Currently I don’t own any pets, but I have in the past. Im available for overnights on weekends. On weekdays I will most likely be available on afternoons and evenings. The house I’m living in is really spacious and it’s in a compound so there is plenty of space for them to roam around in a large, clean house. For dogs or other outdoor pets there is a large yard out in the back, however it is shared with the compound so it is not fenced. The area/compound itself is really nice, modern, and quiet. It’s a great space to take a walk, especially as the weather cools down. If you need any other information, I can share my contact info and provide pictures of the environment.

Sitter Profile Image: Blane H.
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Blane H.
Star Sitter
$36
total per visit
5.0 out of 5 stars
• 27 reviews
13 repeat clients
10 years of experience
Medford, MA, 02155

“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.
Sitter Profile Image: Alison W.
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Alison W.
$30
total per visit
4.8 out of 5 stars
• 17 reviews
3 repeat clients
16 years of experience
Belmont, MA, 02478

“Alison treated our cat very well while we were away. She was able to give him his medicine with no issues and sent us lots of photos of them playing. Our cat can be a bit feisty, so it was great to see her manage him so well.”

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Reagan L.
Sitter Profile Image: Caleb M.
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Caleb M.
$23
total per visit
5.0 out of 5 stars
• 61 reviews
13 repeat clients
15 years of experience
Medford, MA, 02155

“Caleb did a great job watching my two cats over the weekend! My cats were super happy, my house was left spotless, and I got daily updates and photos. Highly recommend Caleb!”

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Olivia S.
Sitter Profile Image: Sabyl C.
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Sabyl C.
$17
total per visit
1 repeat client
10 years of experience
Cambridge, MA, 02140

About: I’ve been caring for pets for as long as I can remember! Growing up, I’ve had the opportunity to care for my own pets as well as those of family, friends, and neighbors. I’m a huge animal lover and genuinely enjoy spending time with animals of all kinds. I would absolutely love the opportunity to meet and care for your fur baby (or babies) and give them all the love, attention, and care they deserve! I’m currently a full-time student, but I only have to be on campus Friday mornings and occasional Wednesday mornings. This gives me a lot of flexibility throughout the week to spend plenty of time with your pet! I always want pets to feel comfortable, safe, and loved while they’re in my care. I follow each pet’s normal routine as closely as possible, including feeding schedules, walks, playtime, medication if needed, and plenty of attention and cuddles. I’m happy to follow any specific instructions or preferences you have for your pet and will make sure they receive the individualized care they’re used to. My goal is to make your pet feel happy and at home while you’re away!

Sitter Profile Image: Thomas & Emma B.
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Thomas & Emma B.
$20
total per visit
5.0 out of 5 stars
• 165 reviews
69 repeat clients
20 years of experience
Cambridge, MA, 02138

“I highly recommend Thomas for anyone in need of pet sitting or cat care services. I had a super last-minute request, and Thomas went out of his way to accommodate my schedule, even coordinating a same-day key handoff. He was punctual, thoughtful, and left sweet notes that made me feel confident and reassured while I was away. Most importantly, he took wonderful care of my cat Gnocchi — it was clear he treated her with genuine attention and affection. If you're looking for someone dependable, caring, and easy to work with, Thomas is an excellent choice.”

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Daniella P.
Sitter Profile Image: Sydney B.
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Sydney B.
$18
total per visit
5.0 out of 5 stars
• 10 reviews
5 repeat clients
4 years of experience
Woburn, MA, 01801

“Sydney house sat for us and took excellent care of our two rabbits. Sydney is courteous, on time and quite pleasant. Highly recommend!”

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Nancy F.
Sitter Profile Image: Anton K.
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Anton K.
$29
total per visit
5.0 out of 5 stars
• 9 reviews
1 year of experience
Malden, MA, 02148

About: I've never owned a dog but I've been helping friends and family to take care of theirs. I'll make sure your pup stays healthy and entertained. I have a very flexible schedule and can accommodate same-day requests. I can pick up your per if necessary. Please don't hesitate to reach out for any questions. My one-bedroom apartment in a pet-friendly building is perfect for a short stay. There's a lovely pond nearby which is perfect for walks.

Sitter Profile Image: Aleia G.
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Aleia G.
$27
total per visit
5.0 out of 5 stars
• 1 review
10 years of experience
Lexington, MA, 02420

About: I have grown up around animals my entire life, making me very comfortable with all pets. With my experience, I feel comfortable keeping up with feeding schedules, refreshing water, administering medications, and providing adequate exercise! I am an active person, so I'm happy to walk, hike, or even run with your furry friend! I consider myself a true animal lover, and I feel my strength is to be able to connect with each dog-and loving on your pet will never be a problem. I’ll keep you updated with photos and messages so you can feel confident your cat is happy and well cared for. Currently, I work mostly from home which means that I have the flexibility to fit most schedules for pet-sitting, drop-ins, and walking-including last minute availability! I am organized and punctual to adhere to schedules, and I also have reliable transportation to get to/from jobs. I have reliable transportation to be able to come to you! I hope to build a trusting relationship with every client, pet and family included, and I feel that starts with a foundation of respect, responsbility, and genuine care! We all want to keep our furry friends happy and cared for, and I want to be a part of that!

Sitter Profile Image: Nick B.
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Nick B.
$25
total per visit
5.0 out of 5 stars
• 24 reviews
10 repeat clients
7 years of experience
Malden, MA, 02148

“Nick did such an amazing job with my 3 month old puppy!! It was her first time being left along for so long and Nick helped her ease into it with awesome play breaks. Nick is the best!”

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

Cat parents share their Rover experiences - Winchester

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5.0 out of 5 stars

I couldn’t be more grateful for the amazing care Xinyuan gave my 2 kitty cats While I was on vacation for a week, she was so sweet with them and took care of all there needs, she left me a detailed message with 10 pictures each time, I felt confident that they were well cared for, I would highly recommend Xinyuan Z to take care of your pets when you are away if I could give 10 stars I would. I definitely will be rebooking her!!

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

Nina consistently amazes us. Our dogs and cat love her when she is able to sit for them. Nina consistently exceeds expectations and allows us to relax knowing our pets are being well taken care of!!

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John G.
Drop-In Visits
5.0 out of 5 stars

I love having Bonnie take care of Max. She is super super responsive and incredibly passionate to taking care of animals. I have relied on her for several visits and will continue to do so!

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

Elisangela has been my go to Rover sitter for a while now and she is always great with my two cats! Highly recommend for anyone in the area.

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

Sharon does a wonderful job with my cat Auggie. I really appreciate how responsive and reliable she is. Highly recommend.

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

Katherine took amazing care of my sweet cat while was out of town. Rebooked already for my next trip, would 10/10 recommend!

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

This was Matilde’s second time watching our cat Frankie and she was amazing as always! She is very attentive to Frankie’s needs, makes the most of the visit by playing with her, and sends great updates and pictures. Matilde is our go-to sitter!

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

Cheryl was able to help us out last minute this time around which was so helpful - we are so grateful we can count on her to help with our cats! They love to see her!

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

Caitlin is awesome, she is very professional and responsive, spent great quality time with my cat and always provide a good summary for every visit.

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YING Z.
Drop-In Visits
5.0 out of 5 stars

Natalie took great care of my cat! She followed all of the directions I provided, took lots of photos, and let me know how the visit went each time.

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Amanda N.
Drop-In Visits
5.0 out of 5 stars

Olivia was great! She was reliable and flexible, was even able to add extra days when our flight got rescheduled due to weather. Will definitely plan to use her again!

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SaadHafsah T.
Drop-In Visits
5.0 out of 5 stars

Monica was very easy to communicate with and took great care of my cat while we were away! Would definitely rebook with her again

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Laura T.
Drop-In Visits
5.0 out of 5 stars

My cat loved Rachel and I am so happy I booked with her! I will be seeking her services again next time I travel :)

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

Kristen took such great care of our cats over the long weekend! She shared photos and sent updates with each visit. We genuinely enjoyed working with her and will be booking her again for future needs.

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Dany O.
Drop-In Visits
5.0 out of 5 stars

Highly recommend Sanela! Sanela was wonderful with our cat. She was attentive, made time for play, and kept us well informed. We're grateful for her help, and I would recommend her to other pet owners.

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

Meg was awesome as always! My cat clearly loves her and she gave him great care. Highly recommend! Will book again

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

Ying is incredibly trustworthy, caring, and attentive to every detail. You can tell she truly loves animals. I highly recommend her! 😻❤️

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zhao l.
Drop-In Visits
5.0 out of 5 stars

Nicole took great care of my cat and followed all directions! I will definitely book with her again.

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

Anna was very responsible with my cat and kept the room very clean! She always stays for the whole 30 mins to give my cat enough play time.

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Vivian Z.
Drop-In Visits
5.0 out of 5 stars

Sasha is great with my senior cat. I know he's in good hands for both drop-in and vacation coverage. Thank you Sasha 🐈‍⬛

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Juliet R.
Drop-In Visits
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Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • 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.

How to book cat sitting

  1. 1. Search

    Browse profiles of sitters near you who offer cat sitting.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
  3. 3. Book & Pay

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Popular requests for cat sitting - Winchester

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Sitters in Winchester average 7
repeat cat sitting clients

FAQs for Cat Sitting - Winchester

Frequently asked questions about Rover

The average cost of Cat Sitting in Winchester is $33 per visit as of November 2026. Most bookings cost between $21 and $44 per visit. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of November 2026, there are 1,576 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.

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

  • 81% of sitters can help with special care needs
  • 86% can help with giving oral medications or injections
  • 87% 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 contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.

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