Dog Walking Cherry Plain

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Cherry Plain, Find top rated dog walking

Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Beth M.
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Beth M.
from
$15
per walk
5.0 out of 5 stars
• 7 reviews
1 repeat client
45 years of experience
Williamstown, MA, 01267

“Beth was wonderful with my puppy taking her for great walks and communicating with me. My puppy was well cared for. Highly recommend.”

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Kerri T.
Sitter Profile Image: Ziv N.
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Ziv N.
from
$16
per walk
20 years of experience
Pittsfield, MA, 01201

About: I've cared for dogs since I was ten years old. I've cared for puppies and senior dogs, and I have far too much experience with elderly dogs near the end of their lives. I love them all more than words, and it's a dream to get paid to play with new dogs! My first responsibility is as a dad (of human children), so I'm available for dogs from the minute the kids leave in the morning until the minute they walk in the door in the afternoon. I have wilderness emergency medical training, and carry basic dog supplies even on short walks around my own block. I treat dogs with the utmost love and care, and only want them to live good and happy lives.

Sitter Profile Image: Samantha P.
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Samantha P.
from
$50
per walk
5.0 out of 5 stars
• 2 reviews
4 years of experience
Petersburgh, NY, 12138

About: I have two dogs of my own who I love more than life itself. I understand the nerves of finding someone to take care of your fur baby while you are away. I love going on walks with my dogs and would love to help ensure your dogs get all the exercise they need while you are busy. I will be taking classes at ACC in the fall, with only one day of in person classes and another day with one online class. I have a part time job I will work on the weekends but my weekdays will be relatively open. I would also love to find regulars to fit into my weekly schedule eventually. I typically play with my dogs in our backyard for a while after they eat breakfast. I try to get some good playtime in before it gets too hot. Especially since one of my dogs (Gunther) is all black and will chase the ball until he can’t anymore, I am very observant of his body language. My other dog (Phoebe) will lie down and not return her frisbee when she needs a break but I have to decide for Gunther when he needs to stop so he doesn’t hurt himself. I only take them on walks in the morning or the evenings when the heat has calmed down and the pavement is cooler.

Sitter Profile Image: Samuel M.
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Samuel M.
from
$25
per walk
18 years of experience
Pittsfield, MA, 01201

About: I am the son of a former vet tech and zookeeper. For as long as I can remember caring for animals of all kinds has been an ingrained mindset and part of my life. I have many years of sitting, fostering, and adopting animals of various species, age, temperament, and medical needs. I pride myself of showing up for my clients and their pets needs and understand the anxieties inherent in watching your home and invaluable pets wellbeing. I work part time with a relatively flexible schedule. If booked, I understand the importance of enrichment and varying levels of time and attentiveness needed. Pets are all unique and I prioritize meeting my client's needs for their pets. Understanding the importance of trust in any pet sitting work is not something I take lightly. Your home and pets wellbeing are my top priority. I am happy to meet client's request for updates with photos and and info to ease any worries.

Sitter Profile Image: Trista S.
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Trista S.
from
$30
per walk
5.0 out of 5 stars
• 24 reviews
10 repeat clients
30 years of experience
Pittsfield, MA, 01201

About: Animals kept me safe my entire life, now I return the favor by keeping your babies safe while you’re away. ❤️ I have been working with animals my whole life. At only 3 I moved in with my step father onto a small farm(yes this means I can feed your chickens, gather your eggs, clean your stalls, and feed your cattle, pigs, or even horses). I spent three years working in the veterinary field where I learned to better understand and triage animal emergency and how to deal with them calmly and safely. I have 3 dogs, and 2 cats of my own as well as a bearded dragon and a few chickens, whom I love more than life. I have minimal boarding experience, but have had or worked with everything from fish and birds, to dogs to cattle, from snakes to horses, and I love each one of these creatures just as much as the rest. I adore all animals, and cherish my pets so much, and finding some one you can trust to REALLY care for them can be a challenge, so let me make your life a little easier with flexible, reliable, patient and gentle care. As a pet mom to 11 furry, scaly, and feathered babies, I know how hard it can be to find reliable pet care. My animals are my children, my babies; the most important things in my world. I promise to love yours the way I’d love my own. I am currently unemployed and taking a leap. What I’d LOVE is to start my own pet care company. I know how hard it is to find pet care in and around the Berkshires, especially the holidays when all the day cares and well known sitters are booked - so let me take some of that weight off you. I’m flexible and reliable and can do drops ins, walks, day stays, over nights, or multiple day stays. I’m open to any animal type, including pocket pets, exotics and special needs. What can I say? Pets are really the only thing most of us like in this crazy world; so it’s kind of the perfect job. 😉 I am open to all types of care, all types of animals, and all types of situations. I have experience in vet medicine and have had elderly and special needs animals my whole life. No matter how long my interaction with your baby is, I assure you it will be filled with love.

Sitter Profile Image: Rita M.
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Rita M.
from
$25
per walk
2 repeat clients
18 years of experience
North Adams, MA, 01247

About: I’ve interned at my local vet clinic for two years now and have recently moved to a paid position as an assistant! through this internship i have not only learned substantial knowledge regarding pet care, such as how to most effectively administer medications, but also discovered my love for pet sitting, as i have become one of the veterinarian’s permanent pet sitter! i also plan to go to vet school after i earn my bachelors degree! i am currently enrolled in college, as well as working various part time jobs so my availability is limited at the moment, but i will try my best to arrange my schedule best for yours ( and your furry friend’s) needs! i’ll treat your furry family like my own! i come with treats ready (with permission of course) and never leave without a game of fetch or whatever else your babies might enjoy! they’ll definitely be the highlight of my day, so i’ll try to be there’s too!

Sitter Profile Image: Diana G.
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Diana G.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
• 11 reviews
2 repeat clients
5 years of experience
Valatie, NY, 12184

“Wonderful, accommodating, and great with my normally shy poodle! Will be booking again. Thank you so much 💕”

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Dayna F.
Sitter Profile Image: Mina N.
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Mina N.
from
$35
per walk
5.0 out of 5 stars
• 2 reviews
1 repeat client
6 years of experience
NY, 12065

About: Hi! 🐾❤️ Animals have always had a special place in my heart! I have over 9 years of experience caring for my own pets and 4 years of experience with Rover and fostering. From playful young ones to senior care who need a little extra patience and love, I’m comfortable caring for pets at every stage of life. I understand that pets are family, and I treat every animal in my care as if they were my own. My goal is to make your pets feel safe, loved, and comfortable while giving you peace of mind when you’re away. I love getting to know each pet’s unique personality, keeping them happy, and making sure they receive all the attention and affection they deserve. I’m responsible, patient, attentive, and happy to accommodate your pet’s individual personality, needs, and routine. I understand how important it is to trust someone with your pets, so I’ll always do my best to give you peace of mind while you’re away. I’m also happy to send regular photo updates so you can see how your little one is doing. Whether your pet is energetic and loves adventures or prefers relaxing and cuddling on the couch, I’ll make sure they get the care and attention they deserve. I can’t wait to meet your fur babies! 🐶🐱💕 I am currently working full time Monday-Friday with fridays work from home and my hours are adjustable between 730-330 and will be available after 3 on week days and free all day Saturday and Sunday. I am also willing to accommodate if needed. I will do what I need to do to ensure yourself and your pet feel comfortable and do what your pet is used too in there routine and comfortable with.If this is a puppy I will help crate and potty train if needed. I do have experience with all sorts of dogs large or small. And cats as well!

Sitter Profile Image: Brian L.
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Brian L.
from
$35
per walk
4.9 out of 5 stars
• 160 reviews
84 repeat clients
20 years of experience
Schenectady, NY, 12306

“Brian was great! I really trusted him to take the best care of Slinky. They're now best friends after this week.”

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GeorgiAnna W.
Sitter Profile Image: Jeffrey S.
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Jeffrey S.
from
$55
per walk
30 years of experience
Falls Village, CT, 06031

About: Hi I'm Jeff an experienced and professional pet sitter, dog walker, and provider of overnight pet care, I offer loving, dependable service that brings complete peace of mind. Whether it's daily visits or extended stays, your pets are treated like family every step of the way. I'm fully licensed, insured, and bonded, and certified in Dog and Cat First Aid & CPR—so you can rest easy knowing your furry companions are in safe, experienced, and genuinely caring hands. I have over 25 years of construction experience. I also offer Handyman Services which can be done while I am at your home. 🐾 Licensed, Insured, and Bonded • Certified in Dog & Cat First Aid and CPR Caring for animals isn't just something I do—it's my full-time profession, my livelihood, and my passion. I take great pride in providing dependable, compassionate care for pets of all kinds, including dogs, cats, birds, fish, chickens, goats, rabbits, hamsters, gerbils, and more. When you entrust me with the care of your beloved companions, I go far beyond basic walks and feeding routines. Their happiness, comfort, safety, and well-being are always my highest priorities. While I know I can never replace your presence, I work hard to provide the love, attention, companionship, and personalized care your pets deserve while you're away. To make life easier for my clients, I also offer handyman and home care services. Whether it's watering plants, bringing in mail, managing trash and recycling, hanging pictures, completing small repairs, painting, or helping with other household tasks, I'm happy to assist while caring for your pets and home. By combining professional pet care with reliable home services, my goal is to give you complete peace of mind, knowing your pets are loved, your home is cared for, and everything is being looked after by someone who genuinely cares. 🐾❤️🏡 When you entrust me with the care of your furry companions, I go above and beyond basic dog walking and playtime; I prioritize their happiness and welfare. Understanding that I can never replace your presence, I tirelessly strive to complement your affection and care by providing the attention and love your pets deserve, even in your absence. I also integrated handyman services into my offerings, recognizing the convenience and practicality of addressing tasks while caring for your pets. Whether it's watering your plants, hanging a picture, managing waste or recycling, or even handling small repairs and painting, I am here to help. Through this fusion of pet care and handyman services, my aim is to simplify your life while ensuring the well-being of your cherished pets and your home.

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The median cost per walk for dog walking in Cherry Plain is $22

Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

How to book dog walking

  1. 1. Search

    Browse profiles of walkers near you who offer dog walking.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform.

Popular requests for dog walking - Cherry Plain

Select a filter and find qualifying sitters offering dog walking.

Sitters in Cherry Plain average 3
repeat dog walking clients

FAQs for Dog Walking - Cherry Plain

Frequently asked questions about Rover

As of October 2026, there are 857 sitters on Rover offering Dog Walking across Cherry Plain. 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 Cherry Plain. 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 , 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 Cherry Plain 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 , 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 .

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

  • 89% of walkers can help with special care needs
  • 93% can help with giving oral medications or injections
  • 96% 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 .

walkers on Rover set their own , 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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