Dog Sitting Winthrop

Book a Winthrop dog sitter to watch your dog in your sitter’s home or yours.

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Over 101
pet parents in Winthrop have booked dog sitting

Winthrop, Find top rated dog 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: Tess S.
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Tess S.
Star Sitter
$19
total per visit
5.0 out of 5 stars
7 reviews
2 repeat clients
7 years of experience
South Boston, Boston, MA, 02127

About: I’ve taken care of all types of dogs for most of my life. I raised, trained, and took care of 2 very different dogs of my own starting 7 years ago. One of them is a rescue with his own specific needs and quirks so I am experienced with reactive and nervous dogs. I also have cared for many other people’s dogs. I’ve walked and care of senior dogs and helped with their unique care needs. I am attentive, responsible, and genuinely enjoy building bonds with the animals I care for. My goal is to make sure your pet feels safe, loved, and happy while you are away. I am currently a part time retail worker, so I have plenty of time and a flexible schedule for carrying for your animals. I am available for walks and in home visits everyday of the week, and I am flexible and easy to reach to set up the exact plan for your animals. I am very aware that each and every pet are very different. That’s why I am attentive and detail oriented in order to properly care for your pet in the way that it needs.

Sitter Profile Image: Erin D.
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Erin D.
Star Sitter
$33
total per visit
5.0 out of 5 stars
52 reviews
14 repeat clients
10 years of experience
Central, Boston, MA, 02113

Erin was great!! My cat can be temperamental and easily overstimulated, he seemed to do really great with her. She went above and beyond of what was asked of her. I got lots of pictures every day of what the two of them were doing. It was nice to come home to his automatic feeder being full, and his litter tray from his automatic litter box emptied. She was very friendly when meeting her, I would absolutely trust her again and rebook in the future. :)

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Felicity K.
Sitter Profile Image: Thelma R.
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Thelma R.
$18
total per visit
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Winthrop, MA, 02152

About: I been dog/cat and reptile sitting for 15 years for friends and family, I love them like my own and excited to work with animals again! I like to go above and beyond and take dogs on extra walks, ensure they are comfortable and feel safe! I love going on walks daily so I’ll always take my dog out to get exercise and care for my little guy (his names gizmo and he’s a big little baby) I always put the animals first and make sure they are situated and cared for by having lovings, attention and made sure they feel safe and comfortable!

Sitter Profile Image: Szu yu K.
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Szu yu K.
Star Sitter
$20
total per visit
5.0 out of 5 stars
9 reviews
3 repeat clients
15 years of experience
Everett, MA, 02149

Szu yu was very communicative and so so caring for my cats. I appreciate her letting me know they were doing alright and sent lots of photos. Reliable, and on time. I highly recommend Szu yu.

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Vica Jean M.
Sitter Profile Image: Elizabeth A.
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Elizabeth A.
Star Sitter
$28
total per visit
5.0 out of 5 stars
36 reviews
12 repeat clients
20 years of experience
Jamaica Plain, Chelsea, MA, 02150

Having someone experienced with giving cats inhalers was the most important thing, and Liz handled it perfectly. This was by far the easiest time leaving the cats alone for me: I trusted Liz completely. Super caring and devoted to making sure our cats had the best time.

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Richard P.
Sitter Profile Image: Nancy A.
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Nancy A.
$23
total per visit
5 years of experience
Chelsea, MA, 02150

About: Love the fluffy babies and I have trained many with basic commands. If there's anything you need, I'm at your service! Please ask questions and I'll be happy to answer. I work full-time, but I have flexibility with my schedule. I get to wfh twice a week and this allows me to be reliable for drop-ins and walks throughout the week. The more details I know about your pet and their quirks, the easier it is for me to take care of them. Creating an environment of trust while you're away is my top priority. I enjoy sending pictures to pet owners whenever they're away so they feel a sense of security while their baby is in good hands.

Sitter Profile Image: Kyle B.
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Kyle B.
Star Sitter
$34
total per visit
5.0 out of 5 stars
155 reviews
53 repeat clients
12 years of experience
South Boston, Boston, MA, 02210

Kyle took amazing care of our cat while we were away. Our reserved kitty warmed up to Kyle immediately and Kyle was extremely warm and responsible. We would be happy for Kyle to watch our pets again soon!

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Margaret F.
Sitter Profile Image: Cooper C.
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Cooper C.
$20
total per visit
5.0 out of 5 stars
6 reviews
1 repeat client
27 years of experience
Boston, MA, 02128

Cooper was an amazing dog sitter for Bailey. She was very communicative, wrote up great summaries for each visit and treated my pup with kindness, care and lots of love. I would highly recommend Cooper for all your pet sitting needs!

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William S.
Sitter Profile Image: Tawana H.
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Tawana H.
Star Sitter
$34
total per visit
5.0 out of 5 stars
121 reviews
49 repeat clients
27 years of experience
Revere, MA, 02151

Tawana took amazing care of my senior cat with health issues and navigated the various medications like an absolute pro. I am looking forward to working with her again.

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Cosima B.
Sitter Profile Image: Jennifer M.
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Jennifer M.
Star Sitter
$34
total per visit
5.0 out of 5 stars
29 reviews
15 repeat clients
8 years of experience
East Boston, East Boston, MA, 02128

Jennifer was amazing caregiving for our senior, anxious pup and we're so grateful for her! She's very flexible, dependable, a clear communicator, and most of all so loving and understanding. Our pup has a lot of extra needs (medicine, a poor bladder, separation anxiety) and Jennifer handled all of it wonderfully. We'd absolutely recommend her!

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Amanda M.
Sitter Profile Image: Diana F.
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Diana F.
$17
total per visit
5.0 out of 5 stars
14 reviews
3 repeat clients
18 years of experience
East Boston, Boston, MA, 02128

About: Hi, I’m a lifelong pet lover with 18 years of experience caring for both cats and dogs — including my current best buddy, a big, lovable Australian Shepherd! I know firsthand how important it is to find someone you can trust with your furry family member. Whether it’s playtime, walks, or cozy cuddle sessions, I treat every pet like my own. Reliable, responsible, and always ready with treats! I have the time and flexibility to offer the best care to your pets. Whether it's cats, dogs, or both, I'm here to help keep your furry family happy, healthy, and loved while you're away. I have a fenced yard! Countless toys and a big furry friend - Australian Shepherd (4) - who is always ready for some fun and companionship!

Sitter Profile Image: Natalie H.
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Natalie H.
$23
total per visit
5.0 out of 5 stars
21 reviews
7 repeat clients
24 years of experience
Revere, MA, 02151

Natalie did a great job taking care of my cat while I was away. She was well cared for. Communication with Natalie was excellent in setting up the visits and during when any potential issues came up.

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Kayla S.
Sitter Profile Image: Ana Paula P.
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Ana Paula P.
$36
total per visit
4.9 out of 5 stars
110 reviews
41 repeat clients
25 years of experience
Revere, MA, 02151

Ana is the best! She’s super responsive and makes sure my kitties are happy and loved while I’m away. So thankful for her for being so caring and attentive.

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Jamielisse G.
Sitter Profile Image: Britney G.
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Britney G.
$34
total per visit
4.9 out of 5 stars
24 reviews
6 repeat clients
10 years of experience
East Boston, Boston, MA, 02128

Britney is sweet and high energy so if your dog is high energy she's a great pick! She's a little more flexible with her schedule but she makes every visit fun and I genuinely felt like my girl was far less lonely with Britney around.

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Kelsi V.
Sitter Profile Image: Ariyana G.
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Ariyana G.
$23
total per visit
1 repeat client
5 years of experience
East Boston, Boston, MA, 02128

About: Experienced dog owner I have a small senior dog of my own and would be happy to look after yours! I have basic experience with Cats as well I'm able to provide services for both dogs and cats Monday-Sunday Please let me know at least a day in advance if you're over 1Mi away from me your pet's safety, trust, and well-being are my top priorities. I take the time to understand your dog’s specific needs, routines, and any special care they may require. I create a safe, comfortable environment where your dog can feel relaxed and secure, whether we’re at home, on a walk, or playing in the yard. With clear communication and a loving approach, I ensure that your dog is always treated with the utmost care, attention, and respect. You can trust that your furry friend is in good hands!

Sitter Profile Image: Tayla W.
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Tayla W.
Star Sitter
$23
total per visit
5.0 out of 5 stars
52 reviews
15 repeat clients
14 years of experience
Chelsea, MA, 02150

About: I’ve been raising dogs since i was a child. I’ve had 4 dogs throughout my life. Out of the most recent 2, one was a senior with heart problems so i have much experience with older dogs and giving medicine if necessary. My other dog is a rescue, i’ve raised since she was 3 months old. In addition to behavioral classes i took with her, i’ve potty trained, crate trained and trained her to have basic skills myself. I’ve raised most of my dogs (there was one adult rescue) from puppy to senior years so i hold much experience with dogs in these age ranges. I can care for dogs that are of all skill levels and ages. My dog and i are able to adapt to any energy level your pup may be at and will always care for them as if they are my own. I currently work full-time but luckily I am hybrid. I work in office Mon, Tues, and Thurs. Otherwise, I will normally always be with your pet unless i must go out and run errands. However, i also love to take my dog wherever i go as long as i know i’m making a quick stop, so if your dog loves car rides we will be together most of their stay. During 2025 holidays i will be at home full time until 1/4/26 I have one sweet puppy who loves other dogs and will gladly welcome them into the home. i tend to keep the house pretty tidy so my dogs can’t get into anything. If there’s anything specific your fur baby needs to avoid let me know. Lastly, i have a camera in my home to watch my puppy if i’m away and as my client i can provide footage of their stay to keep you at comfort.

Sitter Profile Image: Daniela U.
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Daniela U.
$28
total per visit
4 years of experience
Revere, MA, 02151

About: Caring for animals is something I truly enjoy. I’m a responsible, patient, and dependable pet sitter who will treat your furry family member with the same love and attention I would give my own. Whether it’s walks, playtime, feeding, cuddles, or keeping your pet company, I’m committed to making them feel safe, happy, and comfortable. I always follow each pet’s routine and understand how important it is for owners to have someone they can trust. I have a flexible schedule and I’m available most weekdays and weekends. I can accommodate morning, afternoon, and evening visits depending on your pet’s needs. I’m also open to last-minute bookings when possible and committed to being reliable and consistent with every visit. I prioritize your pet’s safety and comfort at all times. I provide a calm, clean, and secure environment and carefully follow all care instructions, including feeding and special needs. Your pet will always be treated with love, attention, and respect.

Sitter Profile Image: Destinee M.
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Destinee M.
$23
total per visit
5.0 out of 5 stars
11 reviews
4 repeat clients
3 years of experience
Revere, MA, 02151

As always, Destinee does a great job of taking care of our "Kids"!! They love the way she pampers them with pets, belly rubs and having their pictures taken. She is just excellent with watching over them, you could not ask for a better person to take care of your "kids" ( the furry ones)

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David Ron D.
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: Theresa R.
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Theresa R.
$28
total per visit
5.0 out of 5 stars
17 reviews
4 repeat clients
9 years of experience
East Boston, East Boston, MA, 02128

About: My partner (Henry) and I love to watch dogs together! We have been surrounded by dogs our whole lives, from small picky eaters to large dogs that can run for miles. Growing up around dogs, we know that they are all different and respond to new people differently, but we have had positive experiences in taking care of family’s, neighbors’, and friends’ dogs in the past and have a ton of energy to do so. We love spending time outside and with dogs and have dog-sat before, including experiences wherein we did not stay in the owners’ home, but visited frequently to walk and feed their dog, and we have dog sat in our own home, so we are comfortable with adapting our services to any of your needs. We both have hybrid work situations, so one of us is always working from home at any given time and are used to being flexible with a pet’s schedule. We take care of pets like they are our own, in the past when we have boarded dogs in our home we have adapted to what the pet is and is not allowed to do (ie sleeping in the bedroom or not etc.)

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

Dog parents share their Rover experiences - Winthrop

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5.0 out of 5 stars

She is incredibly reliable, and my 16 week old puppy absolutely loves her. I can tell she is wonderful with her and genuinely cares about her well-being. She has so much confidence and patience when handling my puppy, and it’s clear that she truly loves dogs. I would 100% recommend her to anyone looking for a trustworthy, caring, and dependable dog walker!

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Sara R.
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

Adrian was excellent with Olivia and was able to accommodate me on short notice. I would definitely use Adrian again and highly recommend them!

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Rob J.
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

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

Ana takes awesome care of my puppy, Rocket! We’ve had her over many times and she never disappoints!

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

Annaliese was amazing with both my dog and cat! She is very accommodating and communicates exceptionally! I would definitely rebook her for future pet care needs!

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

Arianna was amazing! Her responses were timely and professional. She kept me updated on when she was stopping by to take out my pug Winnie, and she sent photos of her on walks, eating, and playing. It was great to know she was in good hands! I would certainly rebook with her again!

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Avonlea C.
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

Amazing care of our dog, added pictures and updates! Would use Alicia again for dog walking and would highly reccomend!

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

Colleen went above and beyond. I could not recommend her more. Her genuine love and care for animals makes her the perfect person to watch your pet!

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

Veronica was amazing! Super responsive, took great care of my older greyhound, and sent awesome videos and photos :) Will be booking again!!

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

Alexis truly saved the day! We had a last minute emergency and she swooped in to help my with me babies. Truly appreciate her professionalism and kindness! 🫶🏼

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

Casey was great! Super attentive to Oso and punctual with her check in times. She made sure to feed him and left very detailed report cards. Overall a very good experience. I will rebook with her again!

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Brunel S.
Drop-In Visits
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Sitters in Winthrop average 6
repeat dog sitting clients

FAQs for Drop-In Visits - Winthrop

Frequently asked questions about Rover

The average cost for Dog Sitting in Winthrop on Rover is $27.75 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 Dog 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 Dog Sitting. For more information on service fees, click here .

As of August 2026, there are 9,884 sitters on Rover offering Dog 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.

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Winthrop choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

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 dog, 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.

While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.

To find sitters in Winthrop with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.

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.

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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