The #1 network of pet sitters & walkers
200,000+ Sitters
1M+ Reviews
95% Perfect 5-star ratings
18M+ Photo Updates

Dog Walkers in Chester, MA

Book a dog walker to give your dog a 30-minute walk around your neighborhood.

Tip: Contact sitters now to confirm availability.

We couldn't find any sitters that matched your criteria.

Try changing your search criteria or updating your location.

Confirmed 4th of July Availability
1. Rachel

Home full time on campus, will run!

Northampton, MA, 01060

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"My dog Teddy has some special rules for handling because he's an assistance dog in training. Rachel was more than willing to accommodate him and work with me... (more)"

Confirmed 4th of July Availability
2. Ben

Work@Home-Frequent yard time/walks

Easthampton, MA, 01027

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Ben N has been a dog owner or cared for dogs for 25 years. He has a special bond with pets and takes the responsibility of their welfare very seriously. Most... (more)"

3. Heather

Home Full-Time Flexible Hours

Pittsfield, MA, 01201

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"I have had a wonderful experience with Heather watching my lovable and high energy golden retriever, Sadie. Heather really cares about animals and cares for ... (more)"

4. Katie

Need a Furry Friend

Williamsburg, MA, 01096

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"I highly recommend Katie as a dog sitter for she is one of the most mature, responsible, hardworking individuals I know, with a commitment and drive for exce... (more)"

5. Kelsey

Experienced Pet Care Provider

Pittsfield, MA, 01201

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Kelsey was great. We were staying nearby at Stockbridge and Kripalu and needed our big English Mastiff looked after for the evening. He had a perfect stay ... (more)"

6. Kelly

Runner who loves dogs!

holyoke, MA, 01040

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Kelly and Logan are so great with our dog! We're so happy to have found them. I am super paranoid about our dog getting loose and they have been very underst... (more)"

Confirmed 4th of July Availability
7. Pat

Watching Over Your Best Friend

Southwick, MA, 01077

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I've loved dogs all my life. My husband and I have owned dogs since we've been married. They are a part of our family, going almost everywhere we g... (more)

Confirmed 4th of July Availability
8. Vanessa

Furbabies are equal to human babies

Easthampton, MA, 01027

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Venessa is truley one of a kind fur-momma! She can senses her own paws to be sure they are secured, fed, and giving paws plenty of attention. She knew how to... (more)"

Confirmed 4th of July Availability
9. Melinda

I love dogs!

Pittsfield, MA, 01201

Dog Boarding, Doggy Day Care

"Melinda is a very experienced dog trainer, handler, and owner. Because of her expertise, people ask her for help in resolving issues with their dogs. She ... (more)"

Confirmed 4th of July Availability
10. Ryan

The Doggie Dood - Pet Services!

Florence, MA, 01062

Dog Boarding, Doggy Day Care

"Excellent care. Maya really loved her time with Ryan and especially with his dog, Willow! She was quite happy and tired when I got her home. (more)"

Available this weekend
11. Erin

Let's go for a walk

Florence, MA, 01062

Drop-In Visits, Doggy Day Care, Dog Walking

"I highly recommend Erin for any job having to do with caring for dogs. She is AMAZING, reponsible, loving to dogs, and simply an absolute pleasure to work wi... (more)"

Available this weekend
12. Jessica

Fenced Yard for Doggy Socializing!

Northampton, MA, 01060

Dog Boarding, Doggy Day Care

About: My husband and I are both post-docs, and I work in Psych and Brain Sciences at UMass with two lovable schnauzer pups and my husband's huskie/shepar... (more)

13. Ava

Home full time - Parks nearby!

Williamsburg, MA, 01096

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: My name is Ava and I am a college student home for the summer. I’m hoping to buy a car soon and am looking to save up some money. Once I graduate I... (more)

14. Emma

Responsible, experienced dog lover!

Lee, MA, 01238

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Emma watched my 10 year old cockapoo Darby. She did a great job taking care of him. She took him for walks and was very loving. Darby has to take quite a bit... (more)"

15. Mattie

Fun and friendly dog lover

Lee, MA, 01238

Drop-In Visits, Doggy Day Care, Dog Walking

"Mattie is amazing with animals! She can care for all sorts of different reptiles as well as dogs and cats. I would definitely recommend Mattie for pet sittin... (more)"

16. Amanda

Fun, Trustworthy,Animal Lover,

Westfield, MA, 01085

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Amanda is a very caring person who loves animals . As a child she took care of her horse , dog & her cat . She has been house sitting for us for five years n... (more)"

17. Abigail

Walks and food makes everyone happy

Florence, MA, 01062

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Abigail is the best and most reliant dog walker! She is 100% reliable, conscientious and dependable! Her love of dogs is the icing on the cake! I high... (more)"

18. Melissa

Melissa lives at end of a dirt rd.

Russell, MA, 01071

Doggy Day Care

"It is my pleasure to recommend Melissa as a caregiver for your furry family member/s. Her care and consideration for an animals individuality and needs is ex... (more)"

19. Ava-Lena

Loving, reliable and attentive!

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Ava-Lena is one of the few people in the world who managed to befriend our nervous little rescue dog--and many have tried! We have a two year old daughter an... (more)"

Confirmed 4th of July Availability
20. Amy

In Love with Animals- Flexible

SOUTHAMPTON, MA, 01073

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Amy has been a volunteer for the Westfield Homeless Cat Project for several years. She has fostered kittens and does a fabulous job. I wouldn't hesitate to... (more)"


What if you're a dog lover who's looking for dog walking jobs? You'll want to check out our information about how to become a dog walker. We're always excited to add new dog walkers to our dog walking service, and our process makes it simple to get your own dog walking business up and running. When you become a Rover dog walker, you benefit from great features including premium pet insurance, a third party background check, and our cashless payment feature for ease and peace of mind. Why not sign up today?

When you're looking for dog walkers near Chester, MA, Rover.com is the simple, smart way to find and book dog walking services. Our Chester dog walkers are dog lovers first and foremost, and 95% of reviewed stays and walks have received a perfect five-star rating. Every new Rover dog walker in Chester, MA must complete a background check. You can see the background check badge on your dog walker's profile, so you know your pet is in safe hands. Whether you need to hire a dog walker for a single outing or want someone to go on regular dog walks with your pet, you're sure to find a great fit for all your dog walking needs in Chester with Rover's dog walking services.

And even better: the price of dog walking in Chester, MA might not be as much as you thought. Whatever your price range, you'll find a dog walker on Rover for almost any budget. Interested in finding out what the typical Rover dog walker expects as a dog walking fee? Visit our average dog walking rates to see the general fees before checking out an individual dog walker's rates.

Looking for a quick solution to your dog walking needs when you're short on time? Then you'll love the Rover dog walking app. The Rover app features hundreds of highly rated, trusted dog walkers, and you can scroll through the options or simply rebook your regular dog walker in seconds. Your dog walker can share real-time photo updates via the Rover dog walking app, and with the app's cashless payment feature you'll be able to compensate your dog walker quickly and safely - no need for cash, checks or tips.

When you book dog walking services on Rover, you'll be able to connect with a dog walker who's a good fit for you, your dog, and your lifestyle. Your walker can provide dog walking updates with start and stop times, a map of their walk with total distance, info about pee, poo, food and water breaks, and photos of your dog in action. Every walk booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee.

In short, when you book Chester dog walking on Rover, your dog gets the loving care they deserve, and you get to relax knowing that your pet is in good hands.

All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.

How it works

Card image cap

1) Browse Sitters

We make it easy to find affordable & reliable sitters near you.

Card image cap

2) Contact Sitters

Chat about your dog and your specific needs. Even meet in person before booking if you really want to.

Card image cap

3) Book & pay

Our platform makes it easy and secure. No cash necessary.

Card image cap

4) Enjoy your trip

Drop off your dog without feeling guilty. Relax with regular photo updates from your sitter.