Dog Walkers in Winchester, NH

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Top rated Winchester dog walkers

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Sitter Profile Image: Haley C.
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Haley C.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
90 reviews
35 repeat clients
17 years of experience
Hinsdale, NH, 03451

I had a work trip and Haley was such a big help walking our pup for the week while I was away. She was very communicative, accommodating, and sent updates everyday. We would definitely ask for her help to care for our pup in the future!

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Elena S.
Sitter Profile Image: Elias V.
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Elias V.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
17 reviews
9 repeat clients
19 years of experience
Putney, VT, 05346

We love Elias!!! He has the knowledge and understanding that all animals are different and knows how to cater to different needs. I know I have nothing to worry about when I'm at work while Elias takes my dog on their off-leash trail hikes! He is very communicative and quick to respond when needed. Both my dog and I are SO happy to have Elias's help every week!

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Bea O.
Sitter Profile Image: Kiersten S.
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Kiersten S.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
55 reviews
16 repeat clients
6 years of experience
Orange, MA, 01364

Kiersten was amazing with my anxious dog! She was patient with him and did a great job making him comfortable. She paid super close attention to his preferences and behaviors, which I really appreciated. She was super reliable as well.

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Miriam K.
Sitter Profile Image: Amadie C.
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Amadie C.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
12 reviews
4 repeat clients
2 years of experience
Swanzey, NH, 03446

About: I love all animals and have fostered for the local Humane Society for the last couple of years. I am drawn to all animals regardless of type, size or breed. Sometimes the more unique the better but there’s something special about every pet. I work remotely so my schedule allows flexibility that is conducive to pet sitting. I am available 7 days a week. I can sometimes accommodate last minute bookings as well. I work remotely and love getting out for walks. I have a flexible schedule but I also know how hard it can be to entrust someone with your fur babies so I am happy to answer any questions you may have.

Sitter Profile Image: Ayden H.
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Ayden H.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
18 reviews
5 repeat clients
15 years of experience
Hinsdale, NH, 03451

Excellent walker engaging with a dog who is not always friendly. Highly recommend!

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Camille S.
Sitter Profile Image: Jorden A.
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Jorden A.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
76 reviews
14 repeat clients
15 years of experience
Rindge, NH, 03461

Jorden is always so good to my dog! I feel so much better knowing Jorden is in the job.

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Chris A.
Sitter Profile Image: Carol O.
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Carol O.
from
$30
per walk
5.0 out of 5 stars
9 reviews
3 repeat clients
28 years of experience
Spofford, NH, 03462

About: I have had dogs & cats in my life since childhood. A parakeet too! I know how close we become to our pets & how important good care is. I have 2 dogs of my own & have devoted myself to giving them the best life possible. I am newly retired so have lots of time to take care of your beloved pets. I love walking & playing with dogs in all kinds of weather. I will take great care of your pets at your home or while you visit Boothbay Harbor for a few hours or for a day! I will follow your instructions, making sure they are happy & safe. We will always have fun! I am retired and, thus, have quite a bit of time to walk & spend time with your beloved pets!! It’s more than a “job” for me. It’s a labor of love as well. I have a fenced in yard that our dogs use and would prefer walking and caring for your dogs at your home where they are more familiar with the surroundings.

Sitter Profile Image: Samantha H.
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Samantha H.
from
$25
per walk
6 years of experience
Ashuelot, NH, 03441

About: I have been around all different kinds of animals since I was a child and have always had a special love for them. All pets deserve unconditional love and kindness, and I am here to help with that! I am working full time from home and am able to adjust my lunch break for pets that need a walk or need someone to check in on them! I am available after 5 on weekdays and am completely free on weekends. Each pet has their own personality, so care will need to be adjusted to meet the needs of each pet. I have plenty experience in high energy dogs as well as very lazy dogs. Some need pets, cuddles, and a walk whereas some will need lots of running around to get their energy out! I am capable of both and will honor what you feel is best for your fur baby.

Sitter Profile Image: Karen K.
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Karen K.
from
$30
per walk
5.0 out of 5 stars
6 reviews
1 repeat client
15 years of experience
Vernon, VT, 05354

About: Growing up in Vermont on a farm, I have been exposed to animals my entire life. I have been taking care of family and friends dogs, horses, cats, guinea pigs, camels (yes, camels) since I was allowed to leave the driveway on my bike as a child. Since leaving high school I took on a professional equestrian career with Wichita riding academy working with rehabilitating abused/ off the track race horses. I have just recently moved to Denver with a fenced in yard and lots of space. I have a dog of my own that is my entire pride and joy who loves spending time with other dogs. Having a fenced in yard, it’s very helpful and handy to those pups with bladder issues to go in and out of the house as needed. My home was completely childproof when I moved in and it’s so far worked for dogs as well. Huge open field located next to the house available for dogs who like to run as well.

Sitter Profile Image: Maggie R.
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Maggie R.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
30 reviews
13 repeat clients
15 years of experience
Gill, MA, 01354

Maggie's walked my pit bull Edna several times. She's easy to communicate with and Edna's well cared for. I would definitely recommend her!

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Aidan N.
Sitter Profile Image: Elizabeth E.
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Elizabeth E.
from
$25
per walk
5.0 out of 5 stars
6 reviews
1 repeat client
33 years of experience
Mount Hermon, MA, 01354

Elizabeth is great! She took great care of our dogs, was easy to communicate with, and very accommodating. Excellent!

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Margaret V.
Sitter Profile Image: Taylor F.
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Taylor F.
from
$25
per walk
5.0 out of 5 stars
3 reviews
1 repeat client
6 years of experience
Hinsdale, NH, 03451

About: Hi there! My name is Taylor. I absolutely love dogs and believe that most times they are better than people. I will take care of your dog(s) as if they are my own. I am available all day every day except between the hours of 3-6 pm. I love running and playing with dogs and do not mind cleaning up messes. I have two dogs of my own, a black lab and a hound mix that I absolutely adore. I love taking them for hikes and just spending as much time with them as I can. If you choose me to help take care of your dog(s), I promise you will not regret it. Thank you for taking the time to look at my profile! I work as a school teacher right now so am only available after 5 during the week and anytime during the weekends. After June 17th, I will be on summer vacation and will be available all day every day. I have a fenced in yard and a black lab that loves other dogs to play with if you'd like for me to bring them to my home to get some energy out.

Sitter Profile Image: Rosalind L.
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Rosalind L.
from
$25
per walk
30 years of experience
Northfield, MA, 01360

About: I have taken care of cats, dogs, Small animals like mice, guinea pigs, fish, turtles. All way to farm animals like sheep, goats and even horses. Due to growing up in small town farming community. Currently I am supervising and helping my teenage daughter care for multiple miniature and full size horses in Leverett MA. I also have two wonderfully spoiled cats and a dog at home. Have some openings in evening and most weekends as at this time I do have a full time 9-5 job. Looking to see where this goes. I do not have fenced in yard but I keep my current dog on tie out or 50ft lead. Very quiet not normally traveled area around house with big yard to play. At clients home depends on environment there. Would prefer no off leash unless securely fenced area.

Sitter Profile Image: Nicole F.
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Nicole F.
from
$20
per walk
5.0 out of 5 stars
1 review
4 repeat clients
2 years of experience
Hinsdale, NH, 05301

About: Hi! I'm Nicole. I'm a software developer & animal lover. I've been around dogs since I was little and have always wanted to adopt one. Caring for dogs with busy owners is a great compromise! Dog owners will love that I will treat their furry pal as if they were mine. They will also love that I have private outdoor space for playtime, anytime, and am right next to central park so there's alot of ground for your furry friend to explore! I truely care about your pets well being so I am consistent with feeding time and will always make sure your furry friend is comfortable, whether its brushing her or refilling her water bowl. I am available Wednesdays and the Weekends for pet sitting, walking, and house sitting. If you are going away for a weekend and need someone to house & pet sit, I'm your girl!

Sitter Profile Image: Christopher B.
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Christopher B.
from
$17
per walk
5.0 out of 5 stars
7 reviews
1 repeat client
22 years of experience
Keene, NH, 03431

About: I've had animals since I was a child. I have helped neighbors, friends, and family members care for their furkids. Walking, feeding, caring for them is the least I can do. I provide them with love as if they are my own. I'm currently working at a job that allows me to come and go as I please with plenty of flexibility. I can help at anytime of any day! I have a fenced yard for my 3 Siberian Huskies and my golden retriever. I also have a Cat, 2 Green Cheek Conures, a Chinchilla, and a Sugar Glider. One of my Dogs is Diabetic so I have plenty of experience with administering oral medications and injections.

Sitter Profile Image: Emily M.
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Emily M.
from
$30
per walk
4.8 out of 5 stars
22 reviews
8 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: Bryana S.
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Bryana S.
from
$30
per walk
5.0 out of 5 stars
4 reviews
2 repeat clients
7 years of experience
Erving, MA, 12498

About: I am an active human and love the companionship of dogs for walks and hikes, as well as a snuggle on the couch. I have cared for puppies as well as senior dogs. I am currently unemployed and have a lot of flexibility in my schedule as well as appreciate the routine of pet care to help me build routine of my own in this moment of unemployment. It is important for me to learn before caring for a pet about their quirks and it is my goal to build trust both with you and your furry friend

Sitter Profile Image: Kayla B.
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Kayla B.
from
$30
per walk
4.2 out of 5 stars
5 reviews
20 years of experience
Keene, NH, 03431

About: I have pet training experience as well as walking, playing, and cuddling! I also currently work at a boarding and daycare facility! I am willing to accommodate to any special requests you may have as well! I have owned dogs for most of my life, including many very different breeds, and have worked with all age groups. I also have experience with other types of animals including many exotics! Animals are my passion and it would be amazing to be able to be around more all the time. I also have a smaller dog that gets along with others, which would be available for me to bring with me if you would like! I hope to hear from you and your fur baby soon! No animal is too big or too small for me to handle! I enjoy working with them all! Please send me a message for more information! I currently work full-time 4 days a week- which is a very easy schedule to work around. I am flexible when it comes to needing care for your babies! I live in a wonderful area that provides many different places to walk when the weather is nice and a small quiet backyard. I also have a small dog that is very comfortable with all types of animals as well.

Sitter Profile Image: Emma C.
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Emma C.
from
$25
per walk
20 years of experience
Bernardston, MA, 01337

About: I started taking care of neighborhood animals when I was 12 years old and continued down this path of animal care and rescue into my adulthood. I took care of a childhood dog for 16 years of my life before rescuing three of my own as an adult. All three of my rescues have their own unique behavioral issues. One I cannot have around small children from trauma inflicted on her by them. My other cannot regulate her emotions when she gets overstimulated, and my youngest is a deaf and mostly blind double merle! I have taken care of my own pets, taken care of countless neighborhood pets, and I have also worked on a horse farm where I was trusted to take care of the horses, donkeys, and pigs. My passion is taking care of animals. My empathy for them is great and its my goal to make sure that even the saddest animals have a full life and find happiness. I also like to make sure that when they are missing their families I can make them as happy, loved and cared for as possible until their families return. I currently work full time and have Mornings, Evenings and Weekends free with flexibility to take time off throughout the day to care for animals who need more frequent attention. Unfortunately, due to my own three rescue dogs at home I will not be able to take pets back to my house for care at this time.

Sitter Profile Image: Scarlett F.
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Scarlett F.
from
$20
per walk
3 years of experience
Keene, NH, 03431

About: I used to babysit for my best friend's family who had three cats and one very active poodle. As well as I've had many pets of my own; cats, dogs guinea pigs, hamsters, you name it. My mother used to be a police dog trainer so i'm very good at handling bigger dogs. I'm very flexible when it comes to time and will work around your schedule. I'm currently home from college for spring break and my time is very open for both weekends and weekdays. My working hours start at 7am and go till 11pm. (But I can fluctuate with your schedule) I have a fenced backyard. And one very friendly small/medium dog, he's a little shy, but he gets along with everyone. I believe that our pet should be treated like family members. Walks, treats, attention and lots of love.

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

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Sitters in Winchester average 4
repeat dog walking clients

Dog Walking FAQs

Frequently asked questions about Rover

Dog walkers on Rover are free to set their rates. The median cost to hire a dog walker in Winchester on Rover as of Jun 2026 was about $25 per walk, after factoring in Rover’s service fees. A dog walker’s rate may also change as you customize your booking to fit your and your dog’s needs.

If you’re searching for a Winchester dog walker for the first time, visit the dog walker’s profile and select the Contact button.

If you have an active request or have booked a service with a dog walker before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 281 dog walkers in Winchester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, dog walkers joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple dog walkers about your booking. Typically, 78% of Winchester dog walkers respond in under an hour.

Dog walkers in Winchester have an average of 16 years of experience. Dog walkers with repeat customers have an average of 4 repeat clients. Experience can vary from dog walker to dog walker, but you can view reviews, years of experience, and number of repeat clients when you compare dog walkers in Winchester.

You can’t always predict a super busy day at work, but you can anticipate your dog’s needs. Instead of rushing home at lunch, book a dog walker to give your dog a 30- or 60-minute dog walk. Your dog walker can stop by as many times as you need—on whatever days you need them. With the Rover app, get a comprehensive Rover Card from your dog walker that includes:

  • Start and stop times
  • A map of their walk with total distance
  • Pee, poo, food, and water breaks
  • Cute photos and a personalized note

There are 281 dog walkers in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 80% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, all dog walkers on Rover have been background checked for you and your dog’s safety.

Yes! Dog walkers joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog walker through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog walker has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog walker requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog walking service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog walker’s cancellation policy.