Pet Sitting Chesterfield

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 4
pet parents in Chesterfield have booked pet sitting

Chesterfield, 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: Janet M.
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Janet M.
Star Sitter
$34
total per visit
4.9 out of 5 stars
• 19 reviews
9 repeat clients
53 years of experience
Chesterfield, MA, 01012

“Janet was absolutely fantastic. She sent me tons of updates and took great care of my anxious girl. My dog warmed up to her immediately and seemed very happy to be in Janet’s company.”

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Ellen N.
Sitter Profile Image: Hillaree H.
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Hillaree H.
$34
total per visit
5.0 out of 5 stars
• 31 reviews
10 repeat clients
40 years of experience
Conway, MA, 01341

“We were very pleased to have Hillaree care for our cat again while we traveling. Her photos and stories from her check-ins make for wonderful updates while away.”

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Gitanjali P.
Sitter Profile Image: Brynn W.
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Brynn W.
$19
total per visit
5.0 out of 5 stars
• 6 reviews
2 repeat clients
1 year of experience
Northampton, MA, 01060

“Brynn was such a wonderful pet sitter for us while we were away for 4 days. She was so thorough and made sure our dog and cat were happy and safe at home without us. A good pet sitter is such an important person to have and we are beyond thankful for her care.”

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Jackie T.
Sitter Profile Image: Annika D.
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Annika D.
$34
total per visit
5.0 out of 5 stars
• 53 reviews
19 repeat clients
6 years of experience
Northampton, MA, 01062

“Annika did an amazing job taking care of my senior cat. She attended to all of her special needs, including insulin injections, with great skill. She kept me informed and sent good pictures, which gave me comfort while traveling. I will absolutely ask Annika to sit again!!”

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Michael C.
Sitter Profile Image: Jaclyn P.
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Jaclyn P.
Star Sitter
$45
total per visit
5.0 out of 5 stars
• 22 reviews
6 repeat clients
15 years of experience
South Deerfield, MA, 01373

“Jaclyn was absolutely wonderful with our newly adopted puppy Pita. From the moment she arrived, she had such a calm, kind energy and seemed to know exactly how to interact with her. Pita has only been in our home for two weeks after coming from a shelter, and she is still very undersocialized and learning to feel safe and confident around people. Jaclyn was incredibly patient, gentle, and competent. She understood Pita and respected her boundaries. By the end of the visit, Pita was comfortable enough to fall asleep near her, which honestly says everything! We highly recommend working with Jaclyn!”

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Carly M.
Sitter Profile Image: Camron Q.
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Camron Q.
$18
total per visit
5.0 out of 5 stars
• 6 reviews
4 years of experience
Northampton, MA, 01062

About: I've worked in multiple areas of animal care including breeding and puppy development, dog daycare, and veterinary care. I have experience caring for all different breeds and ages of dogs! I don't have much professional experience with cats, but I have lived with many cats throughout my life and am a huge cat lover! I do not have any pets myself as I recently lost my dog. So i am in serious need of some dog time! I am available any time after 2:00pm sunday-thursday and all day friday and saturday(: some days i am available earlier than that, typically sundays and mondays im available around 12:30-1:00pm. I am happy to accommodate any of your pet's needs! I can walk, play, just give love, whatever makes your baby feel the most enriched and happy. I know every dog and cat has their own specific needs and I'm very dedicated to that! I live in a small studio apartment. There is plenty of great space to take walks near my house (i live right on the bike trail) but i do not have a fenced in yard. If this sounds like it could be suitable for your pet, i'm more than happy to board them(:

Sitter Profile Image: Ace G.
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Ace G.
$28
total per visit
5.0 out of 5 stars
• 68 reviews
22 repeat clients
9 years of experience
Chicopee, MA, 01020

“Ace is an incredibly attentive, thoughtful, and caring sitter. We booked her to care for our two older cats and she was so communicative and kind to the little guys. One of our cats needs a subcutaneous injection daily, and she did a wonderful job delivering it - even when he was being difficult. I couldn’t recommend Ace enough, and am definitely going to book her again in the future.”

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Matthew M.
Sitter Profile Image: Lori L.
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Lori L.
Star Sitter
$39
total per visit
5.0 out of 5 stars
• 105 reviews
41 repeat clients
15 years of experience
Greenfield, MA, 01301

“We had a great experience with Lori for midday drop-ins during a busy work week! My dog is older, was recovering from surgery, and isn’t always great with strangers — so I wasn’t sure how it would go. But he warmed right up and had great fun on their visits! Lori is responsive, responsible, and great with my dog. I loved the photos of him so happy to see his new pal each day. Will definitely book again! Thanks Lori!”

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Audra
Sitter Profile Image: Mical H.
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Mical H.
$28
total per visit
10 years of experience
Hadley, MA, 01035

About: I've had many different pets including dogs and cats! Experienced with different ages and needs including medications, behavioral, and sizes. Available for boarding, drop in, and walks I currently work mostly from home so I'm flexible for boarding and daytime visits. Love taking long walks and spending time at home with animals. Happy to take dogs on long walks and nature adventures with permission. I have cats and rabbits at home as well. I also have separate space for boarding or day care. Looking for consistent clients to build lasting relationships between me and your pet(s), as well as any last minute needs from new clients.

Sitter Profile Image: Rachel S.
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Rachel S.
$17
total per visit
10 years of experience
Easthampton, MA, 01027

About: Animals have been a part of my life starting from a very young age. As a small child my family fostered dogs and I was taught basic animal husbandry skills from an early age. Growing up we always also had 3 dogs of our own that I was dedicated to caring for. As I grew older my love for animals of all shapes and sizes also grew, guiding me to my career in animal science and veterinary medicine. I have been working in veterinary medicine for 6 years now. I am currently working on obtaining my Veterinary Technician license (CVT). Through my hands-on experience at my job, I have gained many skills. I am proficient and confident in administration of medications, administration of subcutaneous injections, ear cleanings, pedicures, anal gland expressions and more. I also have experience caring for small animals such as rabbits, hamsters, and guinea pigs. Lastly, I have my own flock of chickens and would be happy to care for yours if needed as well! I’m currently working part-time, so I have time in my schedule to play and care for your beloved pets as well. My schedule varies weekly so I would be happy to discuss your needs to see if we would be a good fit for each other! Unfortunately at this time I cannot house any clients pets in my own home, but I am happy to care for your pet in the safety and comfort of your home while you are away. I have various petsitting and housesitting references if needed. Your pet’s safety and happiness are my number one priority.

Sitter Profile Image: Diana D.
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Diana D.
$22
total per visit
5.0 out of 5 stars
• 2 reviews
5 years of experience
northampton, MA, 01060

About: i’ve been dog walking for several years now on a separate app and have experience sitting a dog for a weeks time. i love spending time with all animals ! i work on weekdays 8-4:30 but can do early or evening walks with pets that i am caring for. I am around to dogsit most days. i don’t have space for a dog in my apartment but i always make sure to follow instructions and care for the animals the best i can !

Sitter Profile Image: Aliyah J.
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Aliyah J.
$39
total per visit
5.0 out of 5 stars
• 5 reviews
1 repeat client
9 years of experience
Hadley, MA, 01035

About: Hi, fellow animal lovers. I have years of hands-on experience working with animals of all sizes, breeds, personalities, and temperaments. With a background in veterinary medicine and animal rescue, caring for animals has always been more than a job to me, it’s something I genuinely love. I’m comfortable caring for pets with different personalities and needs, including shy, anxious, energetic, and more challenging animals. I also have experience administering medications and understand the importance of following care instructions carefully to keep your pets safe and comfortable. I’m Fear Free Certified, which means I value reducing fear, anxiety, and stress while creating a positive experience for every pet. My goal is to make your pets feel safe, loved, and cared for while you’re away. Whether your furry companion needs extra patience, medication, playtime, walks, or simply someone to keep them company, I’m happy to provide personalized care and attention. I know pets are family, and I don’t take the trust you place in me lightly. You can expect compassionate care, reliability, and updates to give you peace of mind while you’re away. I look forward to meeting you and your companions! Animal care is already a big part of my daily life! As a veterinary tech, caring for animals is something I’m passionate about both professionally and personally. I prioritize making time for each pet’s individual needs, whether that means feeding, playtime, walks, companionship, or administering medications. I’m organized, attentive, and understand the importance of maintaining pets’ normal routines to help them feel safe and comfortable while their owners are away. I strive to provide reliable, compassionate care and treat every pet as if they were my own. I provide pet care in my clients’ homes, where pets can stay comfortable in their familiar environment and maintain their normal routines. I can assist with feeding, fresh water, litter box cleaning, playtime, companionship, and medication administration as needed. I follow each owner’s instructions carefully and prioritize patience, safety, and low-stress handling. I also provide updates and photos for peace of mind while you’re away. Your pets’ comfort and well-being are always my priority.

Sitter Profile Image: Kelly H.
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Kelly H.
$73
total per visit
5.0 out of 5 stars
• 66 reviews
31 repeat clients
14 years of experience
Otis, MA, 01253

“As always, our dogs were SUPER excited to see Kelly!”

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Eric L.
Sitter Profile Image: James M.
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James M.
$34
total per visit
5.0 out of 5 stars
• 74 reviews
19 repeat clients
5 years of experience
Boston Road, Springfield, MA, 01119

“Love James (and Rachel if needed). I'm totally relaxed when I have to leave since I know my dog is being taken care of by caring and trustworthy people. Great Rover representatives.”

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Donna D.
Sitter Profile Image: Elizabeth E.
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Elizabeth E.
$23
total per visit
5.0 out of 5 stars
• 7 reviews
1 repeat client
33 years of experience
Gill, MA, 01354

“I would recommend Elizabeth for all your dog watching and walking needs. She was very professional and my dogs were friendly with her. She has a lot of experience with dogs. Cheers, Kevin G”

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Kevin G.
Sitter Profile Image: Tosca D.
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Tosca D.
$56
total per visit
5.0 out of 5 stars
• 4 reviews
25 years of experience
Greenfield, MA, 01301

About: I've lived with and cared for dogs for many years of my adult life. I've regularly taken my friends and housemates dogs for runs, hikes, and even watched them for weekends at a time. I enjoy the company of dogs and have a natural affinity for them. I have flexible availability due to working part time from home. I live with my partner in a house that we have all to ourselves, close to many fun hiking and nature spots for dogs to enjoy! Currently working part time and hoping to fill the rest of my time caring for your pets! I have rejoined rover recently to prioritize pet care at this time :) I have a safe and cozy home environment, and am very respectful while in others homes, always hoping to leave it a little better than I found. Either that be a little tidier, a kind note, or a snack, for either humans or pets!

Sitter Profile Image: aiden m.
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aiden m.
$28
total per visit
5.0 out of 5 stars
• 90 reviews
17 repeat clients
13 years of experience
Enfield, CT, 06082

“Loved getting the pictures and Archie had a great time! Thank you!”

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Seta M.
Sitter Profile Image: Anna L.
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Anna L.
$34
total per visit
5.0 out of 5 stars
• 3 reviews
1 repeat client
10 years of experience
South Glastonbury, CT, 06073

About: I have years of experience with dogs of all ages, including seniors. I’m dependable, gentle, and treat every pet with the same love as my own. Pet care is part of my daily routine, including walks, playtime, and attention to each dog’s needs. I am experienced in safely administering medication when needed. I ensure every pet feels safe, loved, and well cared for. I create a safe, calm, and clean environment in both my home and clients’. I follow all instructions carefully to ensure pets feel secure and well cared for.

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

Pet parents share their Rover experiences - Chesterfield

1 / 1
5.0 out of 5 stars

Janet was absolutely fantastic. She sent me tons of updates and took great care of my anxious girl. My dog warmed up to her immediately and seemed very happy to be in Janet’s company.

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Ellen N.
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?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your 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 pet sitting

  1. 1. Search

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

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

    It's that easy! All payments are processed through Rover's secured platform.

Popular requests for pet sitting - Chesterfield

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Sitters in Chesterfield average 5
repeat pet sitting clients

FAQs for Pet Sitting - Chesterfield

Frequently asked questions about Rover

The average cost of Pet Sitting in Chesterfield is $22 per visit as of November 2026. Most bookings cost between $22 and $22 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 928 sitters on Rover offering Pet Sitting across Chesterfield. Enter your ZIP code to see which available sitters are closest to your home.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

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 Chesterfield. On Rover:

  • 90% of sitters can help with special care needs
  • 92% can help with giving oral medications or injections
  • 94% 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 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.

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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