Dog Sitting Chester

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

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Chester, Find top rated dog sitting

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Daniel S.
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Daniel S.
from
$20
per visit
14 years of experience
Londonderry, NH, 03053

About: Hi, I’m Dan! I’m an insured, reliable dog walker available day, night, and weekends to make sure your pup gets the care and exercise they deserve. From small companions to big, strong breeds, I provide safe, loving walks and peace of mind for you. As a dedicated and insured dog walker, I’m here to make sure your pup gets the care, exercise, and attention they need at any hour. When you book with me, your dog’s walk is tailored to their needs — whether that’s a quick potty break, a brisk exercise session, or a relaxed neighborhood stroll. Here’s what you can expect: Personalized Walks – Adjusted to your dog’s size, age, and energy level. Photo & Update After Each Visit – So you’ll always know how your pup did. Safe Handling for All Breeds – From little companions to strong, giant breeds. Flexible Scheduling – Available mornings, evenings, late nights, and weekends. Transportation Services – Safe rides for up to 2–4 dogs (depending on size), whether to the vet, groomer, or another safe destination. Vet/Groomer Appointments – I’ll stay with your pet during the visit. Charged at an hourly rate starting when I pick up your dog and ending when I return them home.

Sitter Profile Image: Jaida L.
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Jaida L.
from
$15
per visit
5 years of experience
Manchester, NH, 03101

About: Ive taken care of all types of animals all my life, and have always made sure that their care is my number 1 priority. I grew up around dogs and always fed bathed and walked them, and made sure they always had the best. As an adult I have a multitude of pets including birds, cats, fish, and lizards, and have a wide range of knowledge on animal behaviors and needs. I currently work full time from 11-7 and typically have Fridays and Saturdays or Saturdays and sundays off, which provides you with time to have your weekends taken care of. Later starts in my day allow me to visit your furry friends before work and to take them out afterwards before bedtime. Your pets will have my full attention and devotion, paying attention to their attitude around me and others, and make sure that they are always comfortable in their surroundings.

Sitter Profile Image: Kayla & Michael F.
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Kayla & Michael F.
from
$25
per visit
5.0 out of 5 stars
• 5 reviews
1 repeat client
20 years of experience
Manchester, NH, 03109

About: We've always had a strong love for dogs! Growing up in a household with dogs, sitting for friends/families dogs, and now having two dogs of our own, we feel confident that your pup will be well taken care of! Unfortunately, both of our dogs have a chronic medical condition requiring very strict food and medication administration. Therefore, we are extremely mindful of dogs who may have special needs, diet restrictions, allergies, medication administration, separation anxiety, etc. We utilize a positive reinforcement approach to training/caring for our dogs and other dogs! Working from home provides us the flexibility to give your pup the love and attention they need! They will never be left alone when boarding with us regardless if it is a weekday/weekend. We understand being away from home can be stressful and want to be there every step of the way! We can accommodate 1 dog per day/night and have a large fenced in backyard for plenty of space for your pups to run around! The fence is 6ft+ and very secure. We also have two very friendly dogs who love nothing more than to play and cuddle on the couch! We only allow dogs from the same home at one time so you can be rest assured your dog will get the attention, love, and safety they need. We will treat your pup like they are our own and understand the anxiety of being away from your furry friend!

Sitter Profile Image: Olivia B.
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Olivia B.
from
$20
per visit
5.0 out of 5 stars
• 247 reviews
65 repeat clients
10 years of experience
Manchester, NH, 03102

“Olivia has been fantastic! I can tell she really loved our pets while we were away. She sent photos and gave us a quick update on how the visit went. We are extremely appreciative of her and will continue using her services in the future. Thanks so much, Oilvia.”

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Danielle T.
Sitter Profile Image: Christopher L.
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Christopher L.
from
$20
per visit
1 year of experience
Hampstead, NH, 03841

About: I am a devoted animal lover that understands the importance of keeping your furry family members safe and happy. I take care of my neighbors pets often and actually have some vet tech experience in my coursework. I want to make you feel safe leaving your pet in good hands and will keep you updated so you have updates as much or as little as you like:) I work full time but with some flexibility to work remote and fairly open evenings and weekends. I prioritize my work above social time so if you need regular pet care I’m happy to provide. I unfortunately cannot host pets in my home as I have a family member who is allergic, but if you are able to accommodate in your home I do my best to leave a space better than I found it and follow all the rules and guidelines that make you’re pet feel as comfortable in their space as possible while you are away.

Sitter Profile Image: Bethany J.
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Bethany J.
from
$20
per visit
5.0 out of 5 stars
• 8 reviews
1 repeat client
18 years of experience
Derry, NH, 03038

About: Hi, I’m Bethany! 🐾 For as long as I can remember, animals have been a central part of my life. I’ve grown up around all types of pets — from energetic puppies to calm senior cats — and caring for them comes naturally to me. Over the years, I’ve provided loving care for countless pets, and it’s something I genuinely enjoy and feel called to do. I’ve worked at a pet store and dog wash, gaining hands-on experience with grooming basics and animal behavior. I’m also an experienced dog walker, comfortable with dogs of all sizes, breeds, and temperaments. Whether it’s administering basic care, giving belly rubs, or making sure your pets feel safe and loved while you’re away, I treat every animal like my own. Whether you need a dependable pet sitter for drop-in visits, overnight care, or daily walks, I’m here to make sure your furry family member is happy, healthy, and well cared for. Let’s connect — I’d love to meet you and your pet! 🐶🐱❤️ I am fully available, stay at home mom. I’ll be available to take your dog out for as many walks or potty breaks as they want / need. I live in a spacious apartment downtown, not far from the Derry rail trail with my husband and Baby. My husband and I are both very much dog people. I take Dog Sitting very seriously and would love to meet your pup.

Sitter Profile Image: Jenna D.
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Jenna D.
from
$18
per visit
3.7 out of 5 stars
• 3 reviews
5 repeat clients
13 years of experience
Haverhill, MA, 01830

About: Hello! My name is Jenna. I absolutely love being around dogs and grew up with them my entire life. My first family dog was a yellow Labrador named Lady, and later, a wonderful black Lab mix named Maddie. While I don’t currently have a dog of my own, I have a lifetime of experience caring for them and plenty of love to give to yours.Because of my active lifestyle, I love spending time outdoors and going on long hikes. I will ensure your dog gets plenty of fresh air, active playtime, and frequent outdoor exercise. I treat every dog with the same kindness and respect I would show a human. In addition to my love for animals, I am a professional schoolteacher who works with young children, which has given me an abundance of patience, care, and reliability. I would be thrilled to treat your dog like a member of the family!

Sitter Profile Image: Michaela L.
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Michaela L.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 124 reviews
41 repeat clients
28 years of experience
Haverhill, MA, 01832

“Michaela was amazing! Came to check on my cat once a day while I was on vacation. Qas very responsive and took on the task with pretty short notice. My cat can be kind of grumpy with strangers, but seemed to really like Michaela! Very communicative and responsive.”

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Elizabeth O.
Sitter Profile Image: Shirley L.
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Shirley L.
from
$30
per visit
5.0 out of 5 stars
• 2 reviews
1 repeat client
12 years of experience

About: You want someone to care about your fur babies when you can't be with them and I'm that person. No I don't have years of being a 'professional' fur baby nanny. I DO have years of experience of enjoying the fulfillment brought to my life by four-legged companionship and seeing how much they too enjoy my company. My kids are grown. This is my way of being useful and filling that void. If you want someone to care for what touches your heart when you can't be there then I'm the person you need. Every grand-puppy should have a grammy like me but only a few like yours will be lucky enough to. I look forward to hearing from you and meeting your fur baby!

Sitter Profile Image: Sam B.
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Sam B.
from
$30
per visit
5.0 out of 5 stars
• 56 reviews
12 repeat clients
5 years of experience
Litchfield, NH, 03052

“Sam always blows us away with the care and effort she puts into taking care of our cat. She consistently keeps us updated and makes us feel like our pet is happy and safe. Thank you, Sam!!!”

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Diana F.
Sitter Profile Image: XI C.
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XI C.
from
$25
per visit
5.0 out of 5 stars
• 12 reviews
4 repeat clients
2 years of experience
Exeter, NH, 03833

“Xi is a cat lover through and through!! I loved the daily cute updates and photos a lot, and I felt good knowing my little furballs were so well taken care of. I’ll definitely be rebooking and referring her. I can’t say enough good things about this experience.”

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Courtney M.
Sitter Profile Image: Santo R.
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Santo R.
from
$22
per visit
6 years of experience
HAVERHILL, MA, 01830

About: I have lots of experiencing taking care of my little dog Roy, a Chihuahua and Boston terrier. I live together with my brother in a suburbia kind of neighborhood and work from home, we have a beautiful backyard and front yard space as well. We love hiking and usually go for a run no matter the weather. As I work primarily from home, I am mostly here to provide personalized care and tend to all their needs. I can be available at random times during emergencies or last minute planning. I live an active lifestyle and can run with the dog to ensure your pal is getting the exercise they need through out the day. I like a challenge and am willing to adhere to special circumstances with your pet.

Sitter Profile Image: Gracie Q.
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Gracie Q.
from
$25
per visit
5.0 out of 5 stars
• 11 reviews
5 repeat clients
15 years of experience
Newmarket, NH, 03857

“Gracie is a true animal lover and it shows upon meeting her. I was nervous to try out Rover for the first time for my senior cat. Meeting Gracie calmed all my nerves - it was so clear she loves and respects all animals. She was prompt on each visit, took care of all my cat’s needs, and even brought him toys. I will surely check to see if Gracie is available anytime I need to be out of town for care of my boy.”

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Tiffany S.
Sitter Profile Image: Indigo T.
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Indigo T.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 12 reviews
3 repeat clients
4 years of experience
Nashua, NH, 03060

“Indigo was great with the cats! They warmed up to Indigo quickly and seemed comfortable. Indigo was communicated well, asked great questions, and took excellent care of our pets.”

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Jay G.
Sitter Profile Image: Andre D.
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Andre D.
from
$20
per visit
4.0 out of 5 stars
• 3 reviews
10 years of experience
Haverhill, MA, 01832

About: Hey, It's Andre and I am ready to Take Booking for All Your Pets ASAP! I Have a Passion for Caring for All Types of Dogs and Cats. Pets are members of the family so keeping them happy and cared for is My Top Priority. I’m very responsible and timely. I take every need into account and will be sure to communicate thoroughly and on time. If I seem like a good fit for your special friend give me a call anytime. I'm a planner so I do take bookings as far in advance as you need whether it’s for Vacation, The Holidays, or even a New Job. Just send me a text and I’ll be sure to respond as soon as I can.

Sitter Profile Image: Yujie Z.
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Yujie Z.
from
$20
per visit
5.0 out of 5 stars
• 9 reviews
4 repeat clients
3 years of experience
Madbury, NH, 03823

“Yujie has been doing regular weekly drop-in visits for our two dogs, and he’s been amazing. He’s very attentive, communicative, and responds quickly. He’s truly gone above and beyond to care for my dogs while I’m working. My dogs, Arnold and Rico, absolutely love Yujie, and he always sends us great pictures during his visits. It gives us such peace of mind knowing they have a caring, reliable person spending time with them during the day—playing with them and giving them potty breaks. I would highly recommend Yujie for anyone looking for pet care!”

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Lisa B.
Sitter Profile Image: Kelsey G.
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Kelsey G.
from
$25
per visit
5.0 out of 5 stars
• 3 reviews
2 repeat clients
15 years of experience
Haverhill, MA, 01832

About: Pet sitter & walker in both Dracut & Haverhill, MA areas Hi, my name is Kelsey, a pet owner of more than 15+ years of 6 animals, both cats and dogs. I have experience with dog walking, sitting, feeding, baths, and spending some time just cuddling! I have a deep unconditional love for animals, and want to provide assistance in any way that I can. I offer sitting, walking, check-in visits & overnight stays. I work full time as an administrative coordinator with flexibility in my schedule to honor pet care. I have the ability to take extra days off, should you require additional hours of care for your fur babies! I am currently looking to make pet walking, visits and sitting a full time job to take up more of my schedule! I have a fenced in yard where both my dogs are safe at home. One of my dogs has a crate at home that she goes into when she wants to be alone or feel safe, as it is not punishment for her! I am happy to abide by any rules you set for your animals, whether that is crate-training, not sleeping on the bed, etc., as well as providing food, water and safety for your animals during my visits.

Sitter Profile Image: Emily F.
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Emily F.
from
$28
per visit
5.0 out of 5 stars
• 46 reviews
20 repeat clients
15 years of experience
New Boston, NH, 03070

“Emily is a fabulous sitter. I felt at ease during my trip knowing that Emily was coming by each day. Our cat Nelly warmed up to Emily immediately which we loved. Will book again ♥️”

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Sarah M.
Sitter Profile Image: Laura D.
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Laura D.
from
$25
per visit
5.0 out of 5 stars
• 2 reviews
1 repeat client
8 years of experience
Methuen, MA, 01844

“Laura was so responsive and easy to communicate with. And Leo loved his time with her.”

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Shana A.
Sitter Profile Image: TJ R.
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TJ R.
from
$30
per visit
5.0 out of 5 stars
• 15 reviews
8 repeat clients
3 years of experience
Lawrence, MA, 01843

About: I’ve had furries since I was 4, dogs, cats, fishes! I believe all dogs and cats deserve to be treated with love compassion and attention no matter the size, breed, or species. I will love your pet like it’s mine and make them feel as comfortable as possible so you and your furry can have calm, fun and comfortable getaway! I work a part-time job so I’ll have plenty of time for the weekend all day long and doggy care/drop in visits/house sittings after 2pm I am available to take care of your furry at your home and provide them with the best care as well as attention and exercise!

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

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  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

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  • Reservation protection

    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

How to book dog sitting

  1. 1. Search

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

    Schedule a free in-person Meet & Greet to find the perfect fit.
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Popular requests for dog sitting - Chester

Select a filter and find qualifying sitters offering dog sitting.

Sitters in Chester average 6
repeat dog sitting clients

FAQs for Dog Sitting - Chester

Frequently asked questions about Rover

As of November 2026, there are 2,692 sitters on Rover offering Dog Sitting across Chester. 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.

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 Chester 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 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.

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 Chester 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 Chester. On Rover:

  • 88% 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.

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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