Dog Sitting Wellesley Hills

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

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Over 43
pet parents in Wellesley Hills have booked dog sitting

Wellesley Hills, 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: Caitlin G.
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Caitlin G.
$18
total per visit
5.0 out of 5 stars
3 reviews
15 years of experience
Wellesley, MA, 02482

Caitlin is amazing!!! She was so loving and caring towards my cats, which gave me so much peace of mind while I was away visiting family for a week. I’ve gone through many cat sitters, many of whom I felt like didn’t give my cats enough love during their visits, and I can confidently say that I felt like my cats were very loved and in good hands. I highly recommend booking with Caitlin!! 💕

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Raquel J.
Sitter Profile Image: Longfei & Luning G.
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Longfei & Luning G.
Star Sitter
$30
total per visit
5.0 out of 5 stars
25 reviews
6 repeat clients
5 years of experience
Waltham, MA, 02451

They were great! My cats both went right up to them and were very happy when I got home. They also sent photos and videos that let me know my babies were taken care of.

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Mira M.
Sitter Profile Image: Sabrina C.
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Sabrina C.
$28
total per visit
5.0 out of 5 stars
7 reviews
1 repeat client
10 years of experience
Watertown, MA, 02472

Sabrina was a fantastic caretaker for my pup during his lunch time walks! She was responsive, gave great updates and I could tell my dog was in a great hands!

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Liz T.
Sitter Profile Image: Isabella A.
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Isabella A.
Star Sitter
$23
total per visit
5.0 out of 5 stars
26 reviews
16 repeat clients
7 years of experience
Wayland, MA, 01778

Isabella did a great job taking care of my cats while I was away! They seemed to really warm up to her, and I felt confident leaving them in her care.

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Olivia M.
Sitter Profile Image: Julia L.
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Julia L.
$23
total per visit
5.0 out of 5 stars
58 reviews
9 repeat clients
10 years of experience
Weston, MA, 02493

Julia took care of our dogs during the winter holidays. She was just perfect! We got daily reports and cute pictures and by Julia’s messages we could see that the dogs were being super well taken care. Julia went far and beyond even accommodating extra days and making sure that the dogs were eating regularly. I certainly recommend her and will look forward to book her again on our next trip.

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Nadia P.
Sitter Profile Image: Jessica W.
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Jessica W.
Star Sitter
$30
total per visit
5.0 out of 5 stars
21 reviews
10 repeat clients
7 years of experience
Waltham, MA, 02453

Jessica was great! Booked a drop-in with short notice. She was responsive, flexible, and showed a care and understanding for my pooch's well-being as well as any concerns I had

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Corwin C.
Sitter Profile Image: Lilly C.
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Lilly C.
$23
total per visit
5.0 out of 5 stars
4 reviews
15 years of experience
North Rosslyn, Wellesley, MA, 02481

About: I’ve loved animals for as long as I can remember. As a child, I dreamed of becoming a veterinarian, and while my path later shifted toward human medicine, my appreciation for animals and caregiving has never changed. Caring for creatures both great and small has always been meaningful to me. I have hands-on experience caring for a variety of animals. I worked at the Natick Organic Community Farm, where I helped care for farm animals and learned the importance of consistency, patience, and attentiveness in animal care. I also spent many years helping take care of my grandfather’s English Setter, Posey — including regular walks, feeding, and companionship — especially as my grandfather became less steady on his feet. In addition, I grew up with cats from the age of eight and am very comfortable with feline care, routines, and personalities. I’ve graduated with majors in Biology and French with a minor in Fine Arts and completed the pre-med track at GWU. I live in Wellesley, MA, for my gap year. I’m reliable, detail-oriented, and calm under pressure. These qualities that are especially important to me as someone pursuing a career in healthcare. I treat every pet as an individual and aim to provide attentive, gentle, and dependable care so you can feel confident your pet is in good hands. I have flexible weekend and weekday availability, easy access to public transportation, and a genuine love for animals. I’m especially happy to help with midday walks, check-ins, and routine care while you’re at work. Specifically, I have free time: Tues: 8am-10am, 3pm-9pm Wed: 8am-11am, 2pm-9pm Thurs: 8am-10am, 3pm-9pm Friday: 8am-9am, 1pm-6pm I prioritize safety, comfort, and a calm environment for every pet. In my home or the client’s, I make sure all spaces are secure, litter boxes are clean, food and water are fresh, and pets are supervised at all times. I follow each pet’s routine closely, provide plenty of attention and enrichment, and check in with owners regularly to keep them updated. I treat every pet as if they were my own, creating a trustworthy, loving, and stress-free environment.

Sitter Profile Image: Michelle S.
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Michelle S.
Star Sitter
$39
total per visit
5.0 out of 5 stars
120 reviews
30 repeat clients
23 years of experience
North Dorchester, Waltham, MA, 02453

Michelle continues to be amazing to my two dogs! I was out of town and felt at ease knowing she would be checking in on them and making sure they had everything they needed, and she provided pictures and a great status update. She also was able to switch time to come a bit later last minute.

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Kerry T.
Sitter Profile Image: zhiyan y.
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zhiyan y.
$19
total per visit
5 years of experience
Wellesley, MA, 02482

About: I have experience caring for dogs of different sizes, breeds, and energy levels. I am comfortable with walking, feeding, playing, and making sure pets feel safe and cared for while their owners are away. I pay close attention to each pet’s needs, routine, and personality to make sure they are comfortable and happy. I am reliable, patient, and truly enjoy spending time with animals, treating every pet as if they were my own. Pet care fits well into my weekly routine as a student because I keep a consistent schedule and have dedicated time before and after classes for walks, visits, and feeding. I’m also usually more flexible on weekends, which allows me to spend extra time with pets. Since I enjoy being around animals and staying active, taking care of pets is something that easily fits into my day. When caring for pets in my home or in a client’s home, I always focus on keeping them comfortable by following their normal routine as closely as possible. This includes feeding them on schedule, giving them fresh water, taking them on walks, and making sure they get plenty of playtime and attention. I also make sure they have a clean, safe, and calm environment where they can feel relaxed. I pay close attention to each pet’s personality and needs, whether they need extra exercise, quiet time, or lots of affection, and I always keep owners updated so they know their pet is in good hands.

Sitter Profile Image: Lior Y.
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Lior Y.
$20
total per visit
4 years of experience
Needham, MA, 02492

About: I have always loved dogs and even have a dog of my own. I am extremely patient and consider myself to be kind. I work as a kindergarten teacher so I am used to taking care of things and tending to their needs. As a kindergarten teacher, I have lots of free time on weekends and school breaks, and I figured the best use of my time would be to do something I already enjoy doing and also help other people out as well. Since I already own a dog of my own I am very conscientious of what dogs can or cannot do, eat, or be near. I try to play with them as much as possible and be friendly with them so they feel comfortable around new people.

Sitter Profile Image: Livia R.
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Livia R.
$27
total per visit
5.0 out of 5 stars
321 reviews
39 repeat clients
5 years of experience
Natick, MA, 01760

I can’t say enough great things about Livia! I needed help very last minute for my two dogs, and she stepped in without hesitation. From the very beginning, communication was quick, clear, and reassuring which made such a stressful situation so much easier. I wouldn’t hesitate to book again and highly recommend her to anyone looking for reliable, compassionate care for their pets! 🐾

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Meghan H.
Sitter Profile Image: Jessie C.
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Jessie C.
$28
total per visit
6 years of experience
Newton, MA, 02465

About: I have been around dogs all of my life, once I was able to properly hold a leash there was no stopping me from hanging out with our 4-legged furry friends! I am a frequent dog walker for coworkers, friends, and family. I also have dog sat on multiple occasions for coworkers, friends, and family whenever they needed me. Most importantly I rescued a very active and very spoiled French Bulldog 6 years ago and he has made my love for dogs even stronger somehow! As much as I love dogs, I also love cats! I will make friends with any sort of animal if I am able to! I work a hybrid schedule for a corporate office. I am in the office on Tuesdays & Wednesdays, and I work from home the other 3 days. Monday, Thursday, Friday I take personal walks on my lunch break as well as after 5pm and would love for a furry friend to join me! Saturdays & Sundays I am open as well! Happy to walk your pup wherever in the neighborhood or area, we'd get out steps in! I have walked dogs in the past ranging from 15lbs, all the way up to 120lbs!

Sitter Profile Image: Tanya M.
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Tanya M.
$28
total per visit
5.0 out of 5 stars
11 reviews
1 repeat client
50 years of experience
Needham Heights, MA, 02494

Thank you Tanya!! She was great with our little Fifi, on time and reliable. Thanks a million.

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Missy L.
Sitter Profile Image: Charlotte C.
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Charlotte C.
$23
total per visit
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Wellesley, MA, 02481

About: Dogs have always been a huge part of my life. I have two Bernedoodles, Cosmo and Shep, who are the loves of my life and have taught me so much about caring for dogs. From daily walks and playtime to keeping them happy, healthy, and comfortable, I’ve gained years of hands-on experience caring for dogs of different personalities and energy levels. I’ll treat your dog with the same care, attention, and affection that I give my own. I currently work as a host throughout the week, which gives me flexibility during the day for dog walks and drop-in visits. I’m completely available throughout the week and love spending my free time with animals whenever I can. Whether your dog needs a walk, a quick check-in, or some extra companionship during the day, I’d be happy to help! Your pet’s safety and comfort are always my top priorities. I understand that every dog has their own routine, personality, and needs, and I take the time to follow your instructions carefully to help them feel comfortable and secure. During walks, I prioritize leash safety, pay close attention to my surroundings, and make sure your dog gets the exercise and attention they need. For drop-in visits, I’ll ensure your pet is cared for according to their normal routine, including feeding, water, potty breaks, playtime, and plenty of affection. I also believe in keeping owners updated with photos and messages so you can have peace of mind while you’re away.

Sitter Profile Image: Natalie W.
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Natalie W.
Star Sitter
$28
total per visit
5.0 out of 5 stars
117 reviews
39 repeat clients
4 years of experience
Newton, MA, 02466

Although we’ve only had one visit so far, I can already tell Winston loves playing with Natalie! He was sleeping hard the moment after she left. I’d highly recommend her to anyone.

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Kelly B.
Sitter Profile Image: Erin C.
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Erin C.
$23
total per visit
5.0 out of 5 stars
2 reviews
10 years of experience
Wellesley Hills, MA, 02481

About: I am a teacher ( and mom) with free time this summer and would love to help care for your dog with walks, play time and overnight care. I have my own 3 year old dog who loves to play with other dogs as well ( but she doesn't have to be included in play or an overnight in your home). Until September I have a flexible schedule and am fairly available weekdays and some weekends with notice. I have an active lifestyle and would enjoy long walks with your dog if needed. I am not offering care in my home at this time. That may change in the future and would depend on the specifics of the dog

Sitter Profile Image: Audrey M.
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Audrey M.
$39
total per visit
5.0 out of 5 stars
71 reviews
30 repeat clients
18 years of experience
Weston, MA, 02493

Audrey did a great job looking after our pet bunny. We came home to find him well fed and happy. House was clean and tidy, and she communicated with us daily. I highly recommend her service!

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Elite B.
Sitter Profile Image: Amanda B.
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Amanda B.
$28
total per visit
5.0 out of 5 stars
4 reviews
1 repeat client
20 years of experience
Wellesley, MA, 02481

About: I’m a teacher with 2 kids and one fur baby. I’m off for the summer and would love to spoil your pooch with all this free time I have! Everyone here LOVES dogs and we would love to give your pooch a safe and loving home while you’re away... or a place to hang during the day! Your pooch is guaranteed to get a lot of love here... even my rescue Roxy hasn’t found a dog she doesn’t love! We are often out for walks around Wellesley college and swims at Centenial. We would love for your pooch to join us on our adventures, daily walks around the neighborhood and snuggles on the couch! I look forward to hearing from you! I hope we can help you out!!

Sitter Profile Image: Niusha N.
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Niusha N.
$34
total per visit
5.0 out of 5 stars
39 reviews
15 repeat clients
10 years of experience
Newton, MA, 02464

Niusha looked after our cat while we were away for the holiday and we were very happy to see the many photos and videos that she shared of our kitty - he was clearly very well loved and taken care of!

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Jonathan B.
Sitter Profile Image: Julia P.
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Julia P.
$28
total per visit
1 repeat client
10 years of experience
Wellesley, MA, 02481

About: Dog-walker, lover, care-taker here! I’ve always loved dogs from a young age and have been exposed to all breeds from the start! I have a rescue lab mix of my own, since 9 weeks old and also live with 2 pitties. I’m here to help with routine dog walks as well as check-ins, feeding, baths.. you name it. I work part time with a scattered shift schedule so my days are always different. What makes me unique with this type of schedule is that I can accommodate your schedule with the openness of mine. I am available most days of the week during the work day and most nights. Not only am I timely and punctual, but I am also full of energy and another human for your dog to interact with during a long work day. I make sure your dog is well cared for in the time that I have for them and take environmental factors into account (weather,etc.). O give extra attention to dogs every time I see them and take my time on walks if I feel they need more time.

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

Dog parents share their Rover experiences - Wellesley Hills

1 / 1
5.0 out of 5 stars

Rose was available with short notice and took wonderful care of our two large golden retrievers! We will absolutely be reaching out to her in the future!!

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Allison Elizabeth A.
Drop-In Visits
5.0 out of 5 stars

Kyra did a great job caring for my two cats, sometimes coming twice a day to feed, water and litter. Kyra also gave ear drops to Nike who had an infection. She sent pictures and was in contact, and I think the cats really liked her. I trust her and would certainly book Kyra again.

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

We had the best experience with Amber! We booked a last minute check-in with her and so glad that we did! Winston was well cared for & by the look of the photos, he was very very happy! Thanks again!

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

Adriana was awesome! She spent time with our dogs this week and took good care of them. She was a good communicator and sent lots of pics! We have already requested to rebook her.

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

Megan did a great job taking care of Gracie and even did some training with her! I highly recommend!

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

Kylie has done an extraordinary job while we were away! very responsive and reliable, and connected wonderfully with our young puppy!

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

First time using a drop-in on Rover and could not have picked a better person in Annika. Communication and service provided were excellent. Highly recommend Annika for anyone needing care for their dogs.

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Mathew K.
Drop-In Visits
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Sitters in Wellesley Hills average 6
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FAQs for Drop-In Visits - Wellesley Hills

Frequently asked questions about Rover

The average cost for Dog Sitting in Wellesley Hills on Rover is $24.42 per visit (as of July 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 July 2026, there are 11,205 sitters on Rover offering Dog Sitting across Wellesley Hills. 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 Wellesley Hills 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 Wellesley Hills 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 Wellesley Hills 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 Wellesley Hills. On Rover:

  • 91% of sitters can help with special care needs
  • 96% 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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