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Dog Walkers in Cheshire, MA

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

Tip: Contact sitters now to confirm availability.
Confirmed 4th of July Availability
1. Rachel

Your dog’s future best friend

Valatie, NY, 12184

House Sitting, Drop-In Visits, Dog Walking

"Rachel was fantastic! Responded quickly and showed up on time, we would definitely recommend to anyone else! (more)"

2. Carol

They all make me smile, doggie love

Bennington, VT, 05201

House Sitting, Drop-In Visits, Dog Walking

"Carol is a very loving person when she is doing something she doesn’t like stopping until it’s done she loves and treats all animals as if they were hers I’v... (more)"

3. Carolyn

IT'S ALL ABOUT THE SNUGGLE

Jacksonville, VT, 05363

House Sitting, Drop-In Visits, Dog Walking

"I have known Carolyn for over 40 years. She is one of the most compassionate, attentive animal lovers I have ever met. She genuinely loves all animals and tr... (more)"

Confirmed 4th of July Availability
4. Joe

I will do whatever it takes!

Guilford, VT, 05301

House Sitting, Drop-In Visits, Dog Walking

About: I have experienced with dog for 5+ years. I have done overnight shifts at a family farm looking after dogs, cleaning up after them, feeding them ev... (more)

Confirmed 4th of July Availability
5. Holly

Know all the best dog walking spots

Williamstown, MA, 01267

House Sitting, Drop-In Visits, Dog Walking

"Holly takes pet sitting to the next level. She has cared for my dogs on numerous occasions. Holly has always stepped up even when it was on short notice. My... (more)"

6. Lauren

Home full time, tons of land!!

Johnsonville, NY, 12094

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

"My experience with Lauren has been great! She's a wonderful pet sitter and my dogs love her. They were well cared for and I don't think they even missed me! (more)"

Confirmed 4th of July Availability
7. Emily

Intuitive Care for High Energy Dogs

Greenfield, MA, 01301

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

"Emily has been great with my very energetic and active labs. She has taken both dogs out on long walks and swims and also cared for them when I've been away... (more)"

8. Carol

Professional Dog Trainer

Hoosick Falls, NY, 12090

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

"BOY CAN I TELL YOU ABOUT CAROL LOVES ANIMALS MORE THAN LIFE IT SELF TAKES THE TIME TO GO THE EXTRA STEPS LISTENS TO THE PETS AND THERE OWNERS NEEDS WILL MAKE... (more)"

Confirmed 4th of July Availability
9. Samantha

Caring Dog Sitter Here to Help :)

Lanesboro, MA, 01237

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Samantha takes care of my 7 year old black lab Mr. Cody. She is loving, caring and extremely responsible. Mr. Cody has extremely dry skin and she has surpr... (more)"

10. Karen

Home full time....trail to walk on

Bennington, VT, 05201

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

"Karen has taken great care of my dog, Maggie. And my dog loves when she watches her. I would highly recommend her with taking care of your pet needs. (more)"

Confirmed 4th of July Availability
11. Ashley

I'll run and play with your dog!

Bennington, VT, 05201

House Sitting, Drop-In Visits, Dog Walking

"Ashley combines a customer service background with a genuine love for animals. I've personally seen her go to great lengths for animals, hers or others, just... (more)"

Confirmed 4th of July Availability
12. Angela

Large Yard for Big Play Times!

Shelburne falls, MA, 01370

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Our family has know Angela for years. We travel several times a year for at least a week and always ask her to take care of our animals. We have a dog, two ... (more)"

Confirmed 4th of July Availability
13. Brooke

Brooke's Dog Sitting

East Greenbush, NY, 12061

Dog Boarding, Drop-In Visits, Dog Walking

About: ****Send your pup on vacation while you travel :)*** I offer dog sitting in your home as well as mine and I have discounted doggie walks **** Hell... (more)

Confirmed 4th of July Availability
14. Claudia

Runs, walks, socialization!

Troy, NY, 12180

House Sitting, Drop-In Visits, Dog Walking

"Claudia's love for animals, especially dogs, is truly amazing. Her knowlege of dogs is quite extensive. Her attitude toward getting to know dogs, and their n... (more)"

Confirmed 4th of July Availability
15. Danielle

10 years of excellent dog boarding!

Pittsfield, MA, 01201

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

About: My name is Danielle and I have been watching dogs forever. I am currently a manager at a local dog daycare and spent 8 years managing the city’s m... (more)

Confirmed 4th of July Availability
16. Kaylee

Dependable, reliable, & dog loving

North Adams, MA, 01247

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Kylie is a great dog owner. She takes care of her dogs very well. She’s taking care of my dog and get a great job for me. She treats animals would love And c... (more)"

17. Kody

Reliable and flexible dog lover!

North Adams, MA, 01247

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

"Great. (more)"

18. Kelsey

Experienced Pet Care Provider

Pittsfield, MA, 01201

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

"My dogs loved her from the very first time they met! My corgi is a high maintenance dog, she was able to assistwith his needs. She sent photos and both of my... (more)"

19. Lauren

Training and care experience!

Greenfield, MA, 01301

House Sitting, Drop-In Visits, Dog Walking

About: I worked with a service dog organization for over 2 years and still work with them occasionally. During my time with the organization, I raised two... (more)

20. Nathan

I'll take your dog to the park

Weststockbridge, MA, 01266

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

About: I love animals I'm kind and friendly I am respectful and responsible. I will keep your dog happy and we will become friends. I've had dogs througho... (more)


When you need dog walking services, we doubt you'll find a better experience than through Rover. Thanks to our wide selection of dog walkers in Cheshire, MA, you'll find that you're able to work with a dog walker who fits in with you, your dog, and your needs. With our start-to-finish approach, your walker can supply you with real-time dog walking updates with start and stop times, a GPS map of their walk, info about any bathroom, food, and water breaks, and pictures of what your dog's been up to. And on top of that, each Rover dog walking booking includes premium pet insurance, 24/7 support, and a reservation guarantee.

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.

Speaking of payment, the cost of dog walking in Cheshire, MA may surprise you - in a good way. That's because there's a dog walker on Rover for nearly every price range and lifestyle. Curious about how much you can expect to pay for dog walking on Rover? Check out our average dog walking rates to get an idea before you start a conversation with an individual dog walker.

When you need dog walking services in Cheshire, MA, you'll be amazed at how easy it is to find the ideal dog walker with Rover.com. We take the guesswork out of selecting the perfect Cheshire dog walking services for your needs. The dog walkers listed on Rover have been reviewed and approved, and - most importantly - they love dogs. In fact, 95% of reviewed stays and walks have a perfect five-star rating. When a dog walker in Cheshire, MA joins our site, they complete a background check. You'll be able to see that they've passed the background check when you view their individual dog walker profile. No matter what level of support you're looking for, you're sure to find a great fit for all your dog walking needs in Cheshire, MA with Rover's dog walking services, whether it's a one-time emergency or a daily appointment.

In other words, when you use Rover to find Cheshire dog walking services, your pet is given the best in loving care and hands-on attention, and you don't need to miss out on that just because life got in the way.

Do you think you have what it takes to become a dog walker for Rover? We're always looking for people with a passion for dogs to join us as a dog walker! If you've been thinking about starting up your own dog walking business, or even if you've been doing it on your own for a while, you'll want to check out our easy sign-up process and consider joining the hundreds of awesome dog lovers who use the Rover dog walking platform. When you become a Rover dog walker, you get access to great support, including premium pet insurance, cashless payment (no more worrying about whether you'll get paid on time), and a third party background check to demonstrate your trustworthiness to prospective clients. Join our pack today!

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

How it works

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1) Browse Sitters

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

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2) Contact Sitters

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

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3) Book & pay

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

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4) Enjoy your trip

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