Pet Sitting Winthrop

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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Over 262
pet parents in Winthrop have booked pet sitting

Winthrop, Find top rated pet sitting

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: Annaliese G.
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Annaliese G.
Star Sitter
$26
total per visit
5.0 out of 5 stars
104 reviews
30 repeat clients
3 years of experience
Chelsea, MA, 02150

Annaliese has checked in on our very shy kitty a couple times - she is one of the few people Lola will come out for. Great communication and detailed report cards. Awesome sitter all around :)

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Kristi I.
Sitter Profile Image: Elizabeth B.
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Elizabeth B.
Star Sitter
$39
total per visit
5.0 out of 5 stars
158 reviews
50 repeat clients
9 years of experience
Winthrop, MA, 02152

Elizabeth took amazing care of our dog, Ruby. She visited multiple times a day for walks, food, playing and cuddles. It was very calming during our vacation that Ruby was in such good hands. Highly recommend Elizabeth!

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Ted W.
Sitter Profile Image: Melissa R.
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Melissa R.
Star Sitter
$36
total per visit
4.9 out of 5 stars
107 reviews
36 repeat clients
12 years of experience
Boston, MA, 02128

Melissa was a wonderful sitter- extremely communicative & responsive. This was my first time hiring a rover/leaving my cat alone & I had such a positive experience. Would highly recommend & would rebook!

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Olivia T.
Sitter Profile Image: Xianxin D.
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Xianxin D.
$26
total per visit
4.9 out of 5 stars
21 reviews
6 repeat clients
8 years of experience
Revere, MA, 02151

Xiaxin is thorough and such a dolllll to my pup. My dog immediately connected with her and her communication was impeccable and intentional. Will always book with Xiaxin

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Christina J.
Sitter Profile Image: Linzi F.
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Linzi F.
Star Sitter
$23
total per visit
5.0 out of 5 stars
125 reviews
41 repeat clients
10 years of experience
Winthrop, MA, 02152

This was my first time using Rover so naturally was quite nervous leaving my cat with a stranger but Linzi was fantastic!! Was a very great experience. Bentley (my cat) loved her and you could tell she was great with animals. She was always on time, even stayed longer some days to spend a little extra time with him, and sent me the best live updates with pictures every visit. I’m 100% using Linzi again whenever I go away and would recommend you do too!

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Lindsay T.
Sitter Profile Image: Jing X.
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Jing X.
$19
total per visit
5.0 out of 5 stars
7 reviews
3 repeat clients
20 years of experience
East Boston, Revere, MA, 02151

Jing is incredibly responsible and genuinely goes above and beyond. It is so hard to find someone who truly understands cats, but she is a natural. She took care of all the essentials perfectly, including keeping a close eye on the automated litter box to ensure it was running smoothly. What really set her apart was the extra care she gave—she took the time to properly groom him and made sure he got plenty of active playtime. To top it all off, her post-visit updates were fantastic; she left highly detailed descriptions after every single visit, which gave me total peace of mind. I trust her completely and cannot recommend her enough!

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Lim P.
Sitter Profile Image: Jennifer B.
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Jennifer B.
Star Sitter
$34
total per visit
5.0 out of 5 stars
221 reviews
37 repeat clients
8 years of experience
Winthrop, MA, 02152

Would definitely book Jennifer again! Our cats were clearly well cared for while we were away, and the house was clean of any pet messes (food, litter, etc.). Would recommend Jennifer for sure!

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Ashley H.
Sitter Profile Image: Nayeli O.
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Nayeli O.
$19
total per visit
5.0 out of 5 stars
5 reviews
10 years of experience
Winthrop, MA, 02152

About: What sets me apart is my patience, reliability, and real experience caring for animals of my own. I have hands-on experience with my bunny and with my first dog, a leash-reactive beagle named Roger, which has taught me calm handling, awareness, and consistency, especially as a pre-vet student currently taking biology and chemistry. During the week, I prioritize my classes and coursework first, then make time to walk and care for Roger, a dog I regularly walk on campus. I’m also committed to my rowing schedule, which keeps me structured and reliable with my time. On weekends when I’m home, I’m available for additional walks and pet care. This routine helps me stay consistent, responsible, and dependable with animals. For dog walking, I always follow the owner’s instructions exactly and prioritize safety at all times. I double-check leashes, harnesses, and collars before every walk, avoid unsafe areas or distractions, and stay alert to my surroundings. I make sure dogs have water before and after walks and return them calmly and securely to their home. Even though I’m new to professional dog walking, I’m very dependable, attentive, and always communicate clearly with owners.

Sitter Profile Image: Amanda S.
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Amanda S.
$23
total per visit
5.0 out of 5 stars
21 reviews
8 repeat clients
20 years of experience
Winthrop, MA, 02152

Amanda is fantastic! She was so attentive and caring for my 2 kitties while I was out of town. She’s very responsive, sent lots of pics and I can tell she truly cares about their well being. Def recommend & I will book her again in the future! Thanks Amanda!

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Jessica N.
Sitter Profile Image: Carol C.
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Carol C.
$18
total per visit
5.0 out of 5 stars
6 reviews
3 repeat clients
35 years of experience
Winthrop, MA, 02152

Carol checked on my cat twice a day while I was away for a week. She was wonderful! She gave him the attention he needed and kept me updated with pictures and details of his day. Carol is reliable and attentive!

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Alena K.
Sitter Profile Image: Sydney C.
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Sydney C.
$28
total per visit
4 years of experience
Winthrop, MA, 02152

About: I have been around dogs all my life and am confident in my ability to care for any size of dog. I am a dog mom of an energetic 3 year old black lab who loves her walks. My career allows me to be available during the day to provide any service that might be needed. I could do multiple times a day or just once. I treat any pet as if they are my own. I will make sure to complete the task ensuring the safety and happiness of your pet as well as respecting your home and boundaries.

Sitter Profile Image: Alexandra L.
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Alexandra L.
$36
total per visit
5.0 out of 5 stars
48 reviews
19 repeat clients
7 years of experience
Winthrop, MA, 02152

Alexandra is professional, caring and just an all around awesome pet sitter. I highly recommend her for a stress-free, happy experience for your pets!

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Rosie M.
Sitter Profile Image: Jennifer M.
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Jennifer M.
$29
total per visit
5.0 out of 5 stars
9 reviews
2 repeat clients
10 years of experience
East Boston, Boston, MA, 02128

Excellent care for my cat including lots of play time and cuddles. Jennifer followed all care instructions closely and sent lots of pictures which I love!! Highly recommend.

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Alicia H.
Sitter Profile Image: Kristen F.
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Kristen F.
$20
total per visit
1 repeat client
10 years of experience
Winthrop, MA, 02152

About: I love all types of dogs! I have been around dogs my whole life! My family and I rescued my pit bull mix From the animal shelter and named him Tucker 3 years ago. He is such a great dog. I love running around with him in my backyard and taking care of him! I also used to watch my aunts dogs for her all the time throughout my life! I used to go to her house and let them out after school. I also used to dog sit for her when she went on vacation. A lot of my friends and family have dogs that I am around all the time as well! I have been around all sizes of dogs such as terriers, labs, pit bulls, golden doodles, shih tzu’s and many more! I am currently working full-time so I am available after 3pm but with the summer coming up I am working part-time so I will be available in the early mornings and late afternoons. I have a dog of my own who I have taken care of for 5 years now. I will provide your dog with a long walk and the proper care and love they need.

Sitter Profile Image: Rob S.
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Rob S.
$26
total per visit
5.0 out of 5 stars
37 reviews
7 repeat clients
14 years of experience
Winthrop, MA, 02152

About: My fiancé and I are truly dog lovers. Over the past 12 years we have had many dogs in our care for various length of time. We have three of our own currently two Italian greyhounds and a female Basenji. I also consistently sit for a family friend’s small terrier, she is a senior girl with us 2-3 times per week. Considering the abundance of dogs in our lives, I would consider myself extremely experienced to handle any dog at any age with any type of potential issues. Dog sitting aside, I am probably a more experienced dog walker than anything else as I walk my three guys three times a day all at the same time. Contact me if you need any help I will take excellent care of your pet , walking , sitting , whatever you need ! With three dogs in our home, I am basically on the clock with them 24/7. For the most part, I am available at all times if you need walking or sitting Our dogs are basically treated like royalty, and will do the same for your pets. I am available for walks up to an hour , feedings and whatever other necessary care comes up. If you need a sitter out home is smoke free and extremely clean and your pet will have an amazing time with us.

Sitter Profile Image: Acacia L.
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Acacia L.
$28
total per visit
5.0 out of 5 stars
5 reviews
1 repeat client
15 years of experience
Winthrop, MA, 02152

Sent me so many cute pictures ? Alicia is fantastic

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Alexandra M.
Sitter Profile Image: Mia O.
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Mia O.
$23
total per visit
5.0 out of 5 stars
5 reviews
3 repeat clients
8 years of experience
winthrop, MA, 02152

Mia was very punctual and followed our directions to a T! She made sure to call me when my cat wasn’t taking his pill right away which I appreciated and she gave me comfort that my cats were taken care of. Thanks so much Mia!

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Seth A.
Sitter Profile Image: Sergio M.
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Sergio M.
$23
total per visit
5.0 out of 5 stars
6 reviews
3 repeat clients
15 years of experience
East Boston, Boston, MA, 02128

We had Sergio look after Nabaut, and honestly, he was fantastic. He really went out of his way to make us feel comfortable, and Nabaut absolutely loved him. If you’re looking for someone reliable and super kind, he’s your guy. Big thumbs up!

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D0rn4
Sitter Profile Image: Alexandra S.
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Alexandra S.
$15
total per visit
5.0 out of 5 stars
3 reviews
2 repeat clients
10 years of experience
East Boston, Revere, MA, 02151

About: Hi there! I am a responsible and reliable pet lover who currently has a chihuahua mix! Would love to care for your pets with the same care and attention that I show my own! Thank you so much for your consideration and I am looking forward to hearing from you and meeting your wonderful pet very soon! I am working remotely 3 days a week so I am available for walks or drop-ins during those days! Tuesday, Thursday and Friday are my work from home days! I am a very safe dog-walker! I will make sure your dogs do not interact with dogs they don't know while on our walks so they stay safe! I will make sure to clean up after them! I am very reliable and will 100% follow any pet care instructions you give/will ask for clarification when needed!

Sitter Profile Image: Zoë M.
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Zoë M.
$18
total per visit
3 years of experience
Winthrop, MA, 02152

About: I love dogs! Walking with dogs and playing with them is one of my favorite things to do. I love running with a high energy puppy, but also love to hang out with more relaxed dogs. I walk dogs almost daily and really enjoy it and love to see them having fun. I love to let the dogs take the lead and we go on our own adventure! I have flexible availability, but am usually always available during the late morning and afternoon. I have experience dog sitting, walking, and grooming. Whatever you need to make sure you and your dog are satisfied, I will do! Don’t hesitate to book a walk so me and your dog can have fun, burn some energy, and get some fresh air!

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The median cost per visit for pet sitting in Winthrop is $25

Pet parents share their Rover experiences - Winthrop

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5.0 out of 5 stars

Euphy (aka Xianxin) was great with our cats! Our most skittish cat - who usually doesn't show her face to strangers - absolutely loved her! Would recommend Euphy's services!

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

Symonne is such a kind soul! I really appreciated them asking very thoughtful questions to keep my pup's routine and preferences at the forefront before starting drop-ins with my dog, Luna. I know Luna was in great hands while I was away. Symonne kept me updated and sent pictures after every visit. :)

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

Arianna was quick to respond to a last second request. Very nice and thorough confirming details, punctual, and very good to our cat. Would happily recommend her.

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

I’ve trusted Monica more than once, and she is truly a wonderful pet sitter. She treats both your home and your pets as if they were her own, with so much care and love. It's such a comfort knowing everything is in great hands while you're away. I highly recommend her, and I will definitely continue to be a repeat customer!

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

Adrian took excellent care of my two girls, Eva and Gretta, for 8 consecutive days. We did a brief meet ans greet before the booking and went through the daily tasks. He was very attentive and respectful. I was able to enjoy my vacations knowing my girls were under Adrian’s care. Recommended and I would personally book again with Adrian. :-)

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

Elizabeth did a wonderful job caring for my three cats while I was away. They were given lots of attention and were well cared for. Elizabeth was professional, flexible, and genuinely enjoyed caring for my cats.

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Anna L.
Drop-In Visits
5.0 out of 5 stars

Linzi is the best sitter we have ever had. I always know my pets get the best care when they’re with her.

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

Nicole was amazing with Shadow. She kept me updated every Morning while I was away on how he was doing and kept me posted with many pictures. It was the first time I used Rover and it was a great experience. I will be contact Nicole again in the future.

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Zully Y.
Drop-In Visits
5.0 out of 5 stars

Annaliese was incredibly thoughtful, caring, and attentive to my kitten. I truly could not have asked for a better pet sitter. She went above and beyond to make sure that Skippito was happy, comfortable, and loved. In addition, she was very communicative and kept me in the loop with how my little guy was doing the entire duration of my trip away.

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

Brittany was so wonderful to work with! She took care of my cat for a weekend and sent a thoughtful update after each visit. I'm so grateful and would definitely choose her again!

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

Jennifer is my preferred sitter for my cat Franklin as I feel totally confident with him in her care. She sends the best photos and always cares for him as if he were her own.

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

Ana has done a great job watching our Dallas every time! We were able to completely put our trust in her when we went out of town for a 4 day long trip. It is nice to know he is in good hands when she sends photos of them playing and is always punctual! I would highly recommend her!

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Victoria L.
Drop-In Visits
5.0 out of 5 stars

Trin always follows through on our discussed arrangements and sends great pictures! She is very reliable, we’ve used her now a number of times for help with our dog. She is super flexible and has been so patient. Highly recommend!

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

Yang took great care of our cat, and we could tell she was satisfied by how much she purred in the videos we were sent. We look forward to requesting if Yang can take care of our cat again!

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

Melis is an amazing pet sitter! She is always so communicative and provides updates every time she visits. My pet is so comfortable with her and it gives me such peace of mind knowing he is well taken care of, I always come home to a happy pet! Cannot recommend Melis enough, I’ve had her pet sit for me multiple times and will continue to ask her to watch my pet! Thank you!

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Kaylee W.
Drop-In Visits
5.0 out of 5 stars

Amanda was amazing with our cats! She was great about keeping us updated and gave them lots of attention.

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

Jing is incredibly responsible and genuinely goes above and beyond. It is so hard to find someone who truly understands cats, but she is a natural. She took care of all the essentials perfectly, including keeping a close eye on the automated litter box to ensure it was running smoothly. What really set her apart was the extra care she gave—she took the time to properly groom him and made sure he got plenty of active playtime. To top it all off, her post-visit updates were fantastic; she left highly detailed descriptions after every single visit, which gave me total peace of mind. I trust her completely and cannot recommend her enough!

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

Alicia is incredibly responsive, did so much with my cat, and made me feel so good about leaving her in his care. Great care and a great person. Highly recommend!!

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

Lexi and her family were so great helping us with our puppy! They were so communicative and we knew he was well taken care of while we were gone.

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

Xinglu was a great cat sitter while I was on vacation. She was extremely communicative, sent regular updates, and really went above and beyond, keeping my space tidy. Most importantly, my cat Ellie seemed so happy, comfortable, and well cared for when I got home. I would absolutely recommend her to anyone looking for a reliable sitter!!

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Carmen B.
Drop-In Visits
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  • 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.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer pet sitting
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Popular requests for pet sitting - Winthrop

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Sitters in Winthrop average 6
repeat pet sitting clients

FAQs for Drop-In Visits - Winthrop

Frequently asked questions about Rover

The average cost for Pet Sitting in Winthrop on Rover is $22.2 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 Pet 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 Pet Sitting. For more information on service fees, click here .

As of August 2026, there are 10,362 sitters on Rover offering Pet Sitting across Winthrop. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Winthrop stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

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.

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

  • 90% of sitters can help with special care needs
  • 95% can help with giving oral medications or injections
  • 95% 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.

A Meet & Greet is a short introductory meeting between you, your pet, 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.

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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