Dog Walkers in Windsor, MA

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

Confirmed availability
This weekend
1. Bree

Experienced Animal Enthusiast!!!

S Deerfield, MA, 01373

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

"We started using Bree just over a week ago and she has been terrific! You can tell right away that she has a special bond with animals. She has been very r... (more)"

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2. Lindsay

I will give your dogs ALL the love

Pittsfield, MA, 01201

House Sitting, Drop-In Visits, Dog Walking

"Linsay has two beautiful dogs of her own. A sweet, loving home, heart to treat any pup to cuddles and a friendly atmosphere. She has raised two very friendly... (more)"

3. 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)"

4. Meagan

Difficult Dog? You can trust me!

Turners Falls, MA, 01376

House Sitting, Drop-In Visits, Dog Walking

"Another great week of walks with Meagan! My dogs are very happy to get walks with her every afternoon. Meagan is patient and gentle and is able to work well ... (more)"

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5. Samantha

Caring Dog Sitter Here to Help :)

Lanesboro, MA, 01237

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

"Forrest was very happy when I got home. Thank you!! (more)"

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6. Carolyn


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)"

7. Casidhe

Our pets are our family!

Averill Park, NY, 12018

Drop-In Visits, Dog Walking

"Casidhe is a true dog lover. She is caring, conscientious, dependable, and takes her responsibilities seriously. She is the first person I call to sit for my... (more)"

8. Matt

Home all hours of the day most days


Dog Boarding, House Sitting, Doggy Day Care, Dog Walking

About: I have had dogs all my life and also have been a dog showman in my younger days participating in dog shows both with the local 4-H program and othe... (more)

9. Shelbie

Large fenced yard in Hatfield

Hatfield, MA, 01038

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

About: I’m a nurse with two dogs and two cats of my own. I love taking my own dogs for long walks and hikes and would love to do the same with your fur ba... (more)

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10. Audrey

Put your paws in good hands!

Greenfield, MA, 01301

House Sitting, Drop-In Visits, Dog Walking

"I found Audrey through a post on craigslist, since I do not have a Rover account, and boy am I glad I did! She was so great with all my pets I was so pleased... (more)"

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11. 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)

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12. Bethany

Big or small, I've done it all.

Pittsfield, MA, 01201

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

"Bethany was great. Came when she said. Did a great walk. Seems very caring. (more)"

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13. Brooke

Brooke's Dog Sitting/Home Full Time

West Sand Lake/East Greenbush/Rensselaer, NY, 12196

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

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

14. Julia

I love dogs more than anything.

Williamstown, MA, 01267

House Sitting, Drop-In Visits, Dog Walking

"After 20 years of gathering dog-sitting and vicarious dog-loving experience to fill the void of her own pup-less domestic life, Julia has recently become a l... (more)"

15. Sierra

I'd love to care for your pets!

Deerfield, MA, 01342

House Sitting, Drop-In Visits, Dog Walking

"I trust Sierra 100% for looking after animals. She knows what she's doing and more importantly, she loves and can tune in to an animals needs. She took amazi... (more)"

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)"

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17. Allison

Fun and loving dog companion

Shelburne Falls, MA, 01370

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

About: I’m a board certified behavior analyst I have experience with using positive reinforcement to shape desired behaviors. I currently have a schedule ... (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)"

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19. Laura

Service dog trainer & doggo lover

Sunderland, MA, 01375

House Sitting, Drop-In Visits, Dog Walking

"Josie and I LOVE Laura! She is very knowledgeable and accomplished. She is just a sweetheart and put up with me being a helicopter mom. I feel great to ha... (more)"

20. Angela

Large Yard for Big Play Times!

Shelburne falls, MA, 01370

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

"We are all so pleased with Angela, especially Charlie. She is flexible, very professional, and clearly loves what she does. Charlie had a great play date of... (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 Windsor, 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 Windsor, 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 Windsor, MA, you'll be amazed at how easy it is to find the ideal dog walker with We take the guesswork out of selecting the perfect Windsor 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 Windsor, 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 Windsor, MA with Rover's dog walking services, whether it's a one-time emergency or a daily appointment.

In short, when you use Rover to find a dog walker in Windsor, you can rest easy knowing that your dog is having a great time.

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!