Dog Walking Winchendon

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pet parents in Winchendon have booked dog walking

Winchendon, Find top rated dog walking

Prices are estimates per walk for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

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Sitter Profile Image: Emily L.
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Emily L.
$23
total per walk
10 years of experience
Winchendon, MA, 01475

About: Growing up with dogs and cats instilled a lifelong love for them and a desire to become a veterinarian. I feed, walk, clean up after, and bathe dogs, giving them exceptional care and attention. Dog /cat sitting is a dream path toward this journey. I’m available for pet care in October and I’m excited to use my love for animals to spend time caring for pets. I’m available for drop in visits from 11 AM to 10 PM and will make sure every pet gets the attention, care, and love they deserve I make sure pets are in a safe, clean, and comfortable environment during every visit. I follow their normal routine, keep doors and gates secure, and make sure they always have fresh water. I’m gentle and patient with every pet and will give them plenty of attention while respecting their personal space. I’ll also keep the pet’s owner updated so they know their pet is safe and cared for.

Sitter Profile Image: Jorden A.
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Jorden A.
Star Sitter
$25
total per walk
5.0 out of 5 stars
• 95 reviews
18 repeat clients
15 years of experience
Rindge, NH, 03461

“Jorden is great with our dog Winston. Jordaen really takes the time to work with Winston on things he is still learning and Jorden let's us know Winston's growth. I would recommend Jorden. ☺️🐶”

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Amy P.
Sitter Profile Image: Amanda H.
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Amanda H.
Star Sitter
$34
total per walk
5.0 out of 5 stars
• 76 reviews
23 repeat clients
15 years of experience
Winchendon, MA, 01475

About: 🐶Insured through The Hartford 🐶IAP Certificate-Dog Daycare Ownership 🐶Fear Free certified 🐶Red Cross Pet CPR + First Aid certified 🐶Daily updates with photos and videos of your fur babies playing and having fun 🐶Off-site hikes and pup adventures with pet parent's approval 🐶Cage free unless specifically requested 🐶Fenced in Dog area off the back deck 🐶Enrolled in grooming classes (in progress) 🐶Experienced in administering both oral and injectable medications 🐶Comfortable handling animals with special needs or following special requests 🐶Small limits of 4 boards at a time and only with pets I already know well that will get along with new pets visiting. I want all pets to be safe and receive all the attention they deserve. Open to discussing individual situations if you aren't comfortable with groups! I am a stay at home mother and pet care is a huge aspect of my daily routine. Where I am home basically all day every day, your pet will always have a watchful eye on them and plenty of love and attention. My two corgis will be out and about and are dog friendly. If I should need to step out I have a Furbo pet camera and crating is an option if that is the owner’s preference. Dog daycare days though I will prioritize being in the home for the day outside of my child drop off and pickups just downtown from me. We have a partially fenced in property so dogs can run free in the gated fenced in area or can be strictly walked and played with on leash- owner preference.

Sitter Profile Image: Majdoline B.
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Majdoline B.
$27
total per walk
5.0 out of 5 stars
• 41 reviews
20 repeat clients
20 years of experience
Ashburnham, MA, 01430

“Majdoline was absolutely wonderful to the girls from the start. She’s punctual, thorough and is communicative. I would definitely recommend her and looking forward to booking her again in the future!”

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Fritzie C.
Sitter Profile Image: Julia P.
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Julia P.
$19
total per walk
15 years of experience
Templeton, MA, 01436

About: Animals are my passion. I've cared for dogs, cats and exotic animals my entire life with a background in Veterinary Medicine and years of education in training/ body language, early socialization and enrichment work. I treat, care for and love all animals as they are my own. I can provided care for pets of all ages with any special needs, medications, grooming needs and more. Reliable, flexible, and trustworthy. Flexible availability! Weekdays, nights and weekends for your pet needs. Available multiple or one drop in(s) for feedings, walks, medications, playtime or general 1:1 time. Can also be available to stay the day. Although I do not board pets at my household or offer overnight stays. I am available for walks and drop in visits ranging from 1-6hrs anytime of the day. I am very respectful of others space and am always very cautious and Intune with your pets well- being.

Sitter Profile Image: Danielle K.
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Danielle K.
$30
total per walk
4.8 out of 5 stars
• 35 reviews
9 repeat clients
20 years of experience
Templeton, MA, 01468

“Dani is AWSOME. She was very patient with my mini schnauzer Toby.He likes to sniff everything and gets upset with other dog walkers when they rush him. She brought her dog Greyhound Zeke who is well behaved and adorable.”

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Jason V.
Sitter Profile Image: Amanda E.
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Amanda E.
$43
total per walk
5.0 out of 5 stars
• 9 reviews
5 repeat clients
30 years of experience
Winchendon, MA, 01475

About: I worked in an exotic vet hospital for 7 years which is also a wildlife rehab facility. Prior to that I have raised and cared for animals of all species of my own my whole life. Whether fury, feather, scales, or more I love just about every living being & critter. I will care for your pets like they were my own. *Making a note that poisonous/venomous or illegal animals are not acceptable or allowed. I have experience with reptiles like geckos, bearded dragons like my own, iguanas, turtles, birds of all shapes, color, and sizes, some farm animals, ferrets, guinea pigs, hamsters, rabbits, and things of the like. Animals that are venomous or harmful are excluded.* I care for and hang out with my fur babies, but there's plenty of room and time for more friendly faces. I work hard so my pets can have a good life. I frequently walk my dogs and can take yours around the neighborhood as well, lots of dog toys, pats and belly rubs, and can crate your pup if needed. I'm also willing to help with some trainings and house breaking if requested.

Sitter Profile Image: Emily J.
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Emily J.
Star Sitter
$28
total per walk
5.0 out of 5 stars
• 45 reviews
22 repeat clients
35 years of experience
Gardner, MA, 01440

“Emily is awesome. Always on time and very good with our Polo, as well as our house. Definitely recommend 100%”

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Steven L.
Sitter Profile Image: Melissa M.
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Melissa M.
$28
total per walk
5.0 out of 5 stars
• 29 reviews
4 repeat clients
20 years of experience
Gardner, MA, 01440

“We are so lucky to found Misty ! She is amazing to both our dogs and literally went above and beyond ! Our dog Skylar is a difficult dog, she is afraid of everything and takes longer time to trust new people, but Misty, she has her magic and now Skylar and Googie are her best friends ! Couldnt thank her enough for taking care our dogs for 3 weeks ! Highly recommended and did I mention she is amazing ?!”

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Christy C.
Sitter Profile Image: Mallory G.
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Mallory G.
$29
total per walk
4.5 out of 5 stars
• 5 reviews
4 repeat clients
11 years of experience
Gardner, MA, 01440

About: I’ve taken care of cats, dogs, snakes, chinchillas, quails, pigs, lizards, Guinea pigs, and bunnies. I am willing to learn how to take care of any animal and have given medicine/received special requests previously I work 4-8 hours a day and one of my jobs is a work from home job. My timing can can be flexible unless I am lifeguarding. I do not offer boarding. I do have pets of my own and would take care of other peoples’ animals according to the owner’s and their vets’ wishes and judgement

Sitter Profile Image: Chastity N.
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Chastity N.
$17
total per walk
4 years of experience
Gardner, MA, 01440

About: I have had a passion for taking care of animals since a young age. I have experience with all types of animals. I worked as a doggy daycare attendant and a veterinary assistant, as well as shelter experience. I'm available for drop in visits and dog walking. I do not have a set schedule at work yet so I will have different availability every week. We do have a backyard which is not fenced in and a porch that I usually block off to let my dogs get outside for some fresh air.

Sitter Profile Image: Colin P.
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Colin P.
Star Sitter
$34
total per walk
5.0 out of 5 stars
• 97 reviews
21 repeat clients
15 years of experience
Fitchburg, MA, 01420

“We love Colin! He takes such amazing care of my puppy Vincent and my dad said he is always so impressed at how patient and kind he is even when the puppy attitude comes out. Thank you Colin!”

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Stephanie G.
Sitter Profile Image: Michelle P.
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Michelle P.
$28
total per walk
5.0 out of 5 stars
• 4 reviews
30 years of experience
Ashby, MA, 01431

About: Owned and taken care of dogs and cats since I was young. Can’t remember a time without having pets! Currently own two crazy pups and two pretty kitties, and can’t wait to meet yours. Have experience with senior dogs, puppies, and everything in between. I am a full time firefighter/EMT, so I only work two 24hr shifts a week, and the rest of the time I get to play with yours, and my own animals! Love to hike or be outdoors with as many pets as possible! If they’re happy, I’m happy! I will follow all rules set for your pet, and be sure to keep their safety at the top of the list! As a pet owner, I can’t imagine something happening to my own animals, and I would never want to let anything happen to yours!

Sitter Profile Image: Kae L.
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Kae L.
$23
total per walk
15 years of experience
Fitchburg, MA, 01420

About: Let me bring your dog on an adventure - my dog walks start at $20 but I do hikes on a sliding scale. I have group play experience, I can bring your dog to a dog park without any fear that your dog will get into any sort of trouble. I'm a quiet, clean, petsitter, I will likely leave your house cleaner than it was when you let me in. "I have worked with Kae, of Little Lyons, for about a year. He is contentious, dedicated, and loving to all the people and pets he comes into contact with. I highly recommend his services and happily look forward to working with him again in the future." - Nicole E. "Kae dogsits for me when I go away on business trips or go into Boston for the weekend, and I could not recommend him more highly! He is caring and attentive to my dog; my dog gets so excited to see him. My dog is medium to high energy and Kae always tires her out. He is extremely knowledgable about dogs and dog behavior and has given me several tools to help keep my dog more mentally engaged and less stressed. Kae is punctual, he remembers all sorts of details about every dog, and he is my go-to whenever I need someone. Best dog sitter/walker in the Providence area!" - Kate R. I have worked with a doggy daycare, where I learnt dog behavior, and positive reinforcement training. I have worked in home pet sitting for dogs, cats, rabbits, snakes, tortoises, geckos, bearded lizards, salt and fresh water fish, for over a decade. Schedule a meet and greet with your pets! LGBTQIA+ friendly, Disability and Sensory Friendly I am a chronically ill artist who has kept strange hours for a very long time. I can fit your furry (or scaly or feathered) family into my schedule without issue. You can rest assured while I am with your pets that they will be well attended to. A typical visit includes 15-20 minutes of play with your pet depending on energy levels, lots of positive attention and love, feeding and making sure they have access to water and making sure any business is done. As an overnight visitor, often for pets with anxiety or special needs/senior pets, I am with your pet in your home from 10pm-8am, plus visits during any of their usual scheduled feedings.

Sitter Profile Image: Apple R.
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Apple R.
$27
total per walk
5.0 out of 5 stars
• 4 reviews
6 years of experience
Leominster, MA, 01453

About: I have had pets since I was 3 years old. I really started to get involved with pet care when I was a preteen. I have done pet sitting with my friends as well. I am going to college to study veterinary technology and am looking to get more hands on experience with dogs and cats! :) ⚠️PLEASE READ BEFORE REQUESTING⚠️:I am currently working part time, so I have plenty of time to watch your pets during the week. However, I may have to leave a few hours a day to go to work! I am able to stay overnight any time. I have a fenced in back yard and I can crate the dogs if needed. I have leashes and harnesses in my home. Everything in my home is pet proofed.

Sitter Profile Image: Patricia H.
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Patricia H.
$28
total per walk
5.0 out of 5 stars
• 3 reviews
1 repeat client
40 years of experience
Princeton, MA, 01541

“Pat was fantastic with my 7 month old puppy who is full of beans! She always came as planned and I could tell that he'd had the company and exercise!”

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Jennifer G.
Sitter Profile Image: Jeffrey W.
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Jeffrey W.
$23
total per walk
5.0 out of 5 stars
• 44 reviews
22 repeat clients
12 years of experience
Sterling, MA, 01564

“Jeffrey is great with our dog Apollo! He’s always very punctual and has a great walk with our very excited German Shepherd. Definitely would recommend!”

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Kayla O.
Sitter Profile Image: Dee G.
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Dee G.
$39
total per walk
5.0 out of 5 stars
• 17 reviews
7 repeat clients
15 years of experience
Fitchburg, MA, 01420

“Dee is compassionate, patient and reliable. She's also a very nice lady. My dog is comfortable with her so I will definitely hire her again”

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Kathie M.
Sitter Profile Image: Emily M.
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Emily M.
$34
total per walk
4.8 out of 5 stars
• 26 reviews
10 repeat clients
8 years of experience
Marlborough, NH, 03455

About: I’ve been around animals since I was 8. I’ve fostered animals, and helped walk, feed, bathe, supply medicine (supplements and pills) to them for friends, family, etc for a little over 8 years now. I’m very experienced with younger dogs and can provide extensive walks / playtime for entertainment and engagement. I also love working with senior dogs as well, and can help provide a calm, stress free environment for them while their owner is away. I’m currently working part-time from home and have a very flexible schedule! I can do drop in visits, overnight stays, and even long weekends / weeks for vacations and getaways! Early mornings and late nights are no problem for me as well. I don’t mind cleaning up messes or puddles, and I can travel very flexibly if needed! I am OK helping with crate training, and providing a positive environment for any pup to grow in while their family is away! I have a fur baby of my own who is almost 4 years old, and absolutely adores other dogs! He is neutered, house trained, and very relaxed. He has been a very good role model for our youngest puppy in the house.

Sitter Profile Image: Julia L.
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Julia L.
$19
total per walk
5 years of experience
Townsend, MA, 01469

About: Been around many different dog breeds and pets since I was a kid. Family and friends have all relied on me to walk, play, and stay with their pets. I am comfortable with small or large dogs! I am a part-time server 3-4 nights a week! My shifts are roughly 4 hours, and I am out of school for the summer so I am available during the weekdays and weekends. I am willing to stay with pets overnight or as long as needed at clients home to ensure their comfortability! I have references that will testify to my willingness to keep their pets safe and satisfied.

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The median cost per walk for dog walking in Winchendon is $25

Dog parents share their Rover experiences - Winchendon

1 / 1
5.0 out of 5 stars

Jorden is great with our dog Winston. Jordaen really takes the time to work with Winston on things he is still learning and Jorden let's us know Winston's growth. I would recommend Jorden. ☺️🐶

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Amy P.
Dog Walking
5.0 out of 5 stars

Jorden is always reliable, and has finally been accepted by my cat, who accepts no one! This is a true testament to Jorden's connection with animals!

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Chris A.
Dog Walking
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Popular requests for dog walking - Winchendon

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Sitters in Winchendon average 4
repeat dog walking clients

FAQs for Dog Walking - Winchendon

Frequently asked questions about Rover

The average cost of Dog Walking in Winchendon on Rover is $16 per walk as of October 2026. Most bookings cost between $16 and $42 per walk. walkers 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 October 2026, there are 1,141 sitters on Rover offering Dog Walking across Winchendon. Enter your ZIP code to see which available sitters are closest to your home.

Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.

Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in your Winchendon. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.

For dog walking bookings, your dog walker can send a Rover Card with details about your dog’s walk. Rover Cards require at least one photo and may include a map of the walking route , the total walk time and distance, and any pee or poop breaks recorded by the walker.

The route map lets you review where your dog was walked in Winchendon after the booking. It is not live GPS tracking.

Have specific details you would like included? Message your dog walker in the app before the walk begins.

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.

Every walker 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 .

Yes, you can find walkers who have experience with handling special pet needs in Winchendon. On Rover:

  • 91% of walkers can help with special care needs
  • 96% can help with giving oral medications or injections
  • 97% 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 walker 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 walker 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 walker for longer stays or first-time bookings. Read our tips for your first Meet & Greet .

walkers 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 walker.

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