Dog Walking in Winchester

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
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Sitter Profile Image: Sandra B.
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Sitter Profile Image: Sandra B.
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1.

Sandra B.

Safe with Sandy!
Woburn, MA, 01801
2.2 mi. away
Doggy Day Care, Dog Walking
5.0 out of 5 stars
19 reviews
12 repeat clients
from
$35
per walk

Sandra was amazing with my dog applesauce. She was very patient with him, he is not a big fan of walks, but she was able to engage with him and get him to walk. I will be booking her again, and I recommend her 1000% ?

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Sitter Profile Image: Chloe P.
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Sitter Profile Image: Chloe P.
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2.

Chloe P.

Experienced, passionate dog walker!
Burlington, MA, 01803
3.8 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
1 review
from
$20
per walk

Chloe is the absolute sweetest. She loves dogs and is so good with our Georgie! Chloe pays such close attention to our dog, plays with her, walks her, treats her with respect but is firm and kind at the same time. When we go out of town Chloe is always our first choice!

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Sitter Profile Image: Brian O.
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Sitter Profile Image: Brian O.
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3.

Brian O.

Smile :)
Burlington, MA, 01803
4.3 mi. away
Doggy Day Care, Dog Walking
1 review
from
$20
per walk

Brian has watched my pug, Oliver, numerous times over the years. He takes excellent care of him (he requires lots of attention both physically and emotionally). Brian follows directions extremely well and makes sure that Oliver (14) is comfortable and happy at all times (Brian has been helping me with Oliver for over 6 years now - they’re best buds). Brian pays close attention to detail, to cleanliness, and to my dog. I think he would be a great fit for Rover. He loves all dogs, and I think any breed/size would do well with him because his energy is so positive and excited. I also live with a lab mix puppy (roommate’s pup) that he has taken care of and every time she even hears his name she gets so excited! I couldn’t recommend anyone more for the job.

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Sitter Profile Image: Erin S.
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Sitter Profile Image: Erin S.
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4.

Erin S.

Your trusted Pet Pal
Somerville, MA, 02145
4.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 review
1 repeat client
from
$20
per walk

Erin is a great caregiver of her personal pets, and has pet sit for my dog with the same care on numerous occasions. He is always excited to see her again. She is well experienced with and loves both dogs and cats as she has been an owner of each.

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Sitter Profile Image: Shrynee D.
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Sitter Profile Image: Shrynee D.
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5.

Shrynee D.

Embracing the Extraordinary Journey
Cambridge, MA, 02140
4.5 mi. away
House Sitting, Dog Walking
5 years of experience
from
$30
per walk

About: As a professional pet sitter, I bring an unparalleled level of dedication, expertise, and specialized skills to offer exceptional care for animals, be it puppies or senior pets. My commitment towards providing the highest standard of service is not only driven by a genuine love for animals but also backed by appropriate training in both puppy care and senior pet support. This essay will delve into the aspects that set me apart from other sitters, focusing on my unique skill set and the high-quality care I provide for these particular age groups of pets I typically work at the restaurant during my free time, which is usually in the mornings or afternoons depending on my schedule. However, I am available to work on weekends from 9 am to 8 PM. Thank you for considering my availability. keeping your furry friends happy and healthy. It's super important to make sure their living area is nice and clean, and that there's nothing dangerous lying around that could hurt them. By doing some regular cleaning and removing any harmful objects, you can help create a safe and comfortable environment for your pets to thrive in.

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Sitter Profile Image: Omar E.
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Sitter Profile Image: Omar E.
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6.

Omar E.

love your dogs like I love mine
Belmont, MA, 02478
3.6 mi. away
Drop-In Visits, Dog Walking
1 review
from
$25
per walk

Omar is very caring towards animals, he makes sure they are well fed, loved, as well as physically well. He plays with them and walks and cleans them if needed. He will treat them as his own.

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Sitter Profile Image: Wendy G.
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Sitter Profile Image: Wendy G.
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7.

Wendy G.

Will treat your dog as if it’s mine
Malden, MA, 02148
4.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
1 review
from
$25
per walk

Wendy is great! Everything you'd want in a host - very responsive, flexible about timing for drop. off and pick-up, and a genuine animal lover. She took care of our fur baby for a week while we vacationed and made sure to send us Pictures once a day! One day we had an emergency, where we couldn’t pick up Chuchi at the groomers and called her and she went for her no questions asked. Would definitely book Wendy again and recommend to anyone.

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Sitter Profile Image: Cathalina M.
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Sitter Profile Image: Cathalina M.
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8.

Cathalina M.

Lover of furry critters!!
Malden, MA, 02148
3.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
122 reviews
49 repeat clients
from
$25
per walk

Cathalina was incredible! Took great care walking my dog Sawyer while I was away on vacation. Will absolutely be booking her again, can't recommend enough!

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Sitter Profile Image: Grace K.
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Sitter Profile Image: Grace K.
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9.

Grace K.

Dedicated care, unique to your pet!
Woburn, MA, 01801
2.1 mi. away
Drop-In Visits, Dog Walking
1 review
from
$28
per walk

I've known Gracie for years, she's very passionate about animals. Her knowledge on cat care is amazing, and she also has experience with senior cats and dogs. she's my go to person whenever I have concerns or needs for my own cats.

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Sitter Profile Image: Jay C.
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Sitter Profile Image: Jay C.
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10.

Jay C.

Let's walk some doggos!
Stoneham, MA, 02180
3.7 mi. away
Dog Walking
5.0 out of 5 stars
6 reviews
3 repeat clients
from
$20
per walk

Jay was the best dog walker I’ve ever had. Sent pictures, super communicative, and took my pup for some extra fun adventures. Would highly recommend!!

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Sitter Profile Image: Heather D.
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Sitter Profile Image: Heather D.
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11.

Heather D.

Rover 101
experienced + passionate pet care
malden, MA, 02148
4.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
26 reviews
16 repeat clients
from
$35
per walk

Heather was great! She was available the same day I booked her which was really helpful and she took cute pics!

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Sitter Profile Image: Caitlin M.
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Sitter Profile Image: Caitlin M.
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12.

Caitlin M.

Rover 101
Cat Whisperer and Canine Companion
Medford, MA, 02155
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
228 reviews
92 repeat clients
from
$36
per walk

Caitlin came to the rescue to help me look after a friend's dog. Caitlin was very patient with my temporary ward ... who is elderly and a bit shouty! Caitlin, walked, petted and even administered eye drops ... something that not everyone could do. Thanks again Caitlin!

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Sitter Profile Image: Joji R.
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Sitter Profile Image: Joji R.
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13.

Joji R.

Paw-some pet care!!
Arlington, MA, 02476
3.5 mi. away
House Sitting, Dog Walking
2 years of experience
from
$25
per walk

About: Hello! Throughout the years I’ve been fortunate enough to care for neighborhood animals as their owners were on vacation! Growing up, I’ve had a handful of pets that I have helped take care of. I look forward to meeting your furry friends and helping you care for them!! As of right now, I am working a part time job that typically consists of night shifts. During the day, I my availability is very flexible. During our walks, I will obey the laws and ensure your dog is always in a safe environment. If at your home, I will clarify the house rules and make sure that you dog is given plenty of attention!

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Sitter Profile Image: Shereen B.
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Sitter Profile Image: Shereen B.
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14.

Shereen B.

Long walks and cuddles!
Arlington, MA, 02476
2.8 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
1 review
2 repeat clients
from
$20
per walk

About: Hello and welcome! I live in a spacious apartment in Arlington Heights with my roommate that loves having canine visitors. I also have close access to Robbins Farm Park, and Spy Pond Park, for longer jaunts. I have over 6 years of dogwalking and boarding experience, as well as always owned a dog as a primary owner throughout my life. However please note I joined Rover in January 2024 to begin managing clients in a more consistent capacity. Banfield Pet Hospital and Arlington Animal Clinic are nearby in case of emergencies, so rest assured that your BFF is only steps away from medical care. I own a car and am minutes away from PetSmart in case of last minute purchases while you are away (dog food, treats, etc) I have a 12 year old Yorkshire Terrier, Buster, is well adjusted to sharing his space during dog boarding. I only accommodate solo stays so your dog will receive the same amount of cozy care I provide to mine. Please contact me when booking to arrange a required Meet and Greet with Buster or if you have questions. Note: the Meet and Greets typically take place as a dog walking near my home. For pet parents that would like to view the boarding space, please inquire during the Meet and Greet booking. I can't wait to be the home away from home for your furry pal! I'm currently working from home so I have a flexible schedule for dog care! For boarding I am available between 7am and 7pm, Monday through Saturday. Sunday boarding is subject to availability. I am open to accommodating your dog the same as you would at home ie. crate keeping, bottled water drinking, etc. Please specify as needed

Sitter Profile Image: Tama C.
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Sitter Profile Image: Tama C.
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15.

Tama C.

I love all dogs!
Medford, MA, 02155
3.3 mi. away
Dog Walking
2 reviews
from
$25
per walk

I met Tama 3 years ago and she has always cared for animals and people. Tama has a dog Goliath who she loves more than anything, she’s always responsible when it comes to feeding, playing with, and taking her dog on a walk. Tama would be a great pet caregiver for rover.

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Sitter Profile Image: Angelic S.
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Sitter Profile Image: Angelic S.
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16.

Angelic S.

Rover 101
Puppy Love
Medford, MA, 02155
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
25 reviews
10 repeat clients
from
$25
per walk

Angelic accommodated a last-minute walk and did a great job walking my very anxious pup. Much appreciated!

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Sitter Profile Image: Erin L.
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Sitter Profile Image: Erin L.
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17.

Erin L.

Rover 101
Fitness goals! Pet More dogs!
Woburn, MA, 01801
2.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
60 reviews
30 repeat clients
from
$22
per walk

Erin is awesome! She is very quick to respond when I reach out and is very flexible with walk times. I feel very comfortable with my dog in her hands. Remington will definitely be becoming one of her regulars!!

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Sitter Profile Image: Sophia M.
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Sitter Profile Image: Sophia M.
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18.

Sophia M.

Energetic pet sitter and dog walker
Arlington, MA, 02476
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
16 reviews
7 repeat clients
from
$20
per walk

Sophie was a wonderful walker for Atlas. She came right on time everyday for the full week and Atlas loved walking with her. Thank you, Sophie, we look forward to having you walk Atlas again in the future!

Sitter Profile Image: Francesco A.
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Sitter Profile Image: Francesco A.
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19.

Francesco A.

Enjoy animals and the outdoors!
Winchester, MA, 01890
0.6 mi. away
Drop-In Visits, Dog Walking
10 years of experience
from
$20
per walk

About: I grew up with my black lab so I have experience walking and training a high energy dog who loves to run and eat anything she can get access to. I love the outdoors and spent a ton of time in the woods exercising my dog (and me). I also have taken care of cats and rabbits for friends. I'm currently in graduate school studying Earth Science. Whether I'm on break or just have time between classes I'm using that opportunity to meet new animals and support my education. My dog Riva always has the best beds and toys along with new collars and leashes. She is extremely fashionable. I like to make sure my pets are as comfortable and relaxed as possible around their home and I'll give the same treatment to any pet I take care of.

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Sitter Profile Image: Prabitha N.
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Sitter Profile Image: Prabitha N.
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20.

Prabitha N.

Lots of exercise, attention & love
Medford, MA, 02155
1.6 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
12 reviews
4 repeat clients
from
$60
per walk

Huge thanks to Prabitha for expertly caring for my anxious dog Noelle. Prabitha was thoughtful and gentle during introduction which eased my dog's nerves. We received regular photo and video updates which made it clear they understood his needs. Highly recommend Prabitha for compassionate and personalized pet care, especially for anxious dogs.

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Winchester Dog Walking ratings

Overall Rating:
4.9 out of 5 stars

Dog walkers in Winchester are rated on average 4.9 out of 5 stars based on 55 reviews.

Rover also offers Dog Walking in:

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Are you a dog lover who wants to know more about how to turn your passion into profit? There's lots of opportunity to earn money as a dog walker in Winchester, MA. If you're not sure where to start, visit our page about how to become a dog walker. We're always happy to include new dog walkers in our dog walking service listings, and the simple review process means you can start your own dog walking business in no time. We also take the hassle out when it comes to paperwork, because all our Rover dog walkers have access to premium pet insurance, a third-party background check, and cashless payment feature, so you don't have to worry. Join our pack today!

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.

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 Winchester, 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 Winchester, 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 Winchester 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 Winchester, 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 Winchester, 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 Winchester, you can rest easy knowing that your dog is having a great time.

Dog Walking