Dog Walking Wingdale

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pet parents in Wingdale have booked dog walking

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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: Casey S.
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Casey S.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
89 reviews
26 repeat clients
16 years of experience
Wingdale, NY, 12594

Casey was great with my two dogs, particularly tender with both of my pups anxiety and quirks. She even brought treats for them! Casey was easy and timely in communication. Will definitely be hiring her again!

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Nidhi K.
Sitter Profile Image: Isabella M.
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Isabella M.
from
$20
per walk
5 years of experience
Wingdale, NY, 12594

About: Ever since I was young, I have had a strong love for animals, especially dogs. I grew up surrounded by dogs and currently have two of my own. Over the years, I have pet-sat for neighbors and friends, and I always enjoy caring for and spending time with their pets. At college I am part of a club where we work with and volunteer at the local animal shelters. There are photos on my profile that highlight some of the events on campus I have volunteered at to raise money for the puppies at the local animal shelter. I do also have experience with horses. My experience has strengthened my passion for working with animals and reinforced my commitment to providing them with attentive, compassionate care. I currently have a lot of availability to be able to take care of your pets. I can board and attend to your pets any day of the week. I have a fenced-in backyard and two dogs of my own as well. I have a 10-month-old male English Bulldog and a 3-year-old female French Bulldog. They are both very friendly and love playing with other dogs. At your residence, I will respect any boundaries you may have and provide the best service I can.

Sitter Profile Image: Meghan C.
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Meghan C.
Star Sitter
from
$24
per walk
5.0 out of 5 stars
10 reviews
6 repeat clients
19 years of experience
Sherman, CT, 06784

About: Rescue dogs capture my heart! Experienced walking senior, rescue and fearful dogs. Happy to check in on your furry family with a cute photo to give you peace of mind while you are away. New to the area and have a flexible day time schedule M-F to visit and walk your pets! Happy to give medicine with instructions as needed. I’m happy to follow your preferred exercise plan for your pet, a snuggle and checkin, a wander around the yard or a walk around the block.

Sitter Profile Image: Jessie G.
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Jessie G.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
218 reviews
92 repeat clients
10 years of experience
Patterson, NY, 12563

Jessie always responds in an instant and is incredibly reliable. She made time to meet us before we hired her and is always professional. Highly recommend!

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Lia B.
Sitter Profile Image: Don H.
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Don H.
from
$20
per walk
30 years of experience
Pawling, NY, 12564

About: My name is Don H. I am a professional pet sitter, dog walker and licensed dog trainer for 30+ years. I have been in the pet industry for many years, this is what I do full-time and love every minute of it. I care for all breeds of dogs and cats and also reptiles, fish, rodents, goats, horses I will e-mail/text or phone you updates and photos of your pet while you are away. I would love to help you out whether you need a pet/house sitter, dog training, dog walking, trail walks or your dog to be transported to Vet or Groomer. Your pet will be well cared for whether in your home or ours. I am a call way. Sincerely, Don My clients will give reference to how trustworthy and experienced I am when caring for pets in your home. I have respect for your property and even go the extra mile making sure your home is maintained and your pets are safe. I will take in your mail, water plants, take out your garbage/recyclables at no charge. Overnights include picking up after your pet inside and out. Why I love dog sitting I have been around all animals my whole life, I started my journey when I became a certified dog trainer. I also worked as a Kennel Manager for a medium-size kennel in Greenwich, CT. People tell me that I have great patience and calmness when working with difficult dogs. my goal is to help owners and their pet's to become one. I have over 25 years experience as a dog trainer and pet care provider. About my yard Yes i do have a backyard. Although it is not fenced in but I have tree barriers that keeps them safe. I also am close to a dog friendly park where all dogs are on leashes. I will not take a dog off leash when he/she is in my care. My experience administering medication Yes with my kennel experience, I am very comfortable administering medication. I am also comfortable administering shots for dogs and cats. I am a full time pet care provider and a dog walker and i have been training dogs of all breeds for the last 30 years. I give all my furry guest lots of play time and walks and all of our guest hang out with us we are cage free unless your owner wants your dog to sleep in one

Sitter Profile Image: Stacy S.
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Stacy S.
from
$15
per walk
1 year of experience
New Milford, CT, 06776

About: I’ve cared for both small and large dogs, including two small dogs and a German Shepherd. I’m comfortable with feeding, walking, routines, and providing calm, reliable care. Available for drop-ins, dog walks. House sitting/ and overnight available Friday's and Saturday's. Hours flexible except 5:00–10:00am on weekdays only. Please contact me for booking. Responsible and attentive, I ensure a safe and secure environment for your pets. I follow your routine, handle pets gently, and maintain a clean and comfortable space.

Sitter Profile Image: Kevin H.
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Kevin H.
from
$30
per walk
5.0 out of 5 stars
16 reviews
6 repeat clients
20 years of experience
Pawling, NY, 12564

Kevin is excellent! Caring, flexible, affable and communicates well with his clients! Maxx and Daisy love him, and I don't have to feel bad going to work and leaving them!

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Anna Lillian M.
Sitter Profile Image: Kristen B.
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Kristen B.
from
$30
per walk
5.0 out of 5 stars
4 reviews
3 repeat clients
29 years of experience
Poughquag, NY, 12570

Great service. Wonderful with Aero and Diana.

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Godfrey M.
Sitter Profile Image: Brianna G.
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Brianna G.
from
$15
per walk
10 years of experience
Wingdale, NY, 12594

About: I have taken care of dogs, cats, and other pets for years. Even the shyest of animals end up loving me! I gave my dog the best 13 years he could ever have, and I want to share my love and kindness with other pets while alleviating duties from busy owners. I am a junior at Florida Institute of Technology studying Forensic Psychology and minoring in PreLaw with a light workload, as I am finishing up my time in college. Caring for pets would drastically increase my happiness and improve my quality of life, give the animals necessary exercise, fresh air, and extra love/attention, and help busy owners tend to their duties and relieve their stress. I have a decent living space in my pet-friendly apartment with backyard greenery and a cozy room for them to rest if the animals need.

Sitter Profile Image: Emily M.
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Emily M.
Star Sitter
from
$35
per walk
5.0 out of 5 stars
19 reviews
6 repeat clients
20 years of experience
New Milford, CT, 06776

Emily is amazing with my dog, Luna. She is always flexible when it comes to scheduling walks and makes sure Luna has everything she needs. Emily is incredibly caring and loving toward her. Luna gets so excited every time Emily arrives to pick her up for a walk. I really appreciate how thoughtful and reliable she is. I wouldn’t choose anyone else to walk Luna!

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Lexi B.
Sitter Profile Image: Stephen N.
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Stephen N.
Star Sitter
from
$50
per walk
5.0 out of 5 stars
33 reviews
13 repeat clients
25 years of experience
Beekman, NY, 12533

Steve does a great job with my dog Gus. He came and walked him while I was out of town for a few days. He has very great communication and I felt confident leaving Gus in his care. Highly recommend to others!

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Sean H.
Sitter Profile Image: Sabrina W.
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Sabrina W.
from
$30
per walk
4.6 out of 5 stars
7 reviews
2 repeat clients
20 years of experience
New Milford, CT, 06776

Sabrina is very easy to work with. My dog liked her right away. I definitely recommend her.Look forward to working with her again.

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Rodney F.
Sitter Profile Image: Jillian P.
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Jillian P.
from
$18
per walk
5.0 out of 5 stars
5 reviews
1 repeat client
15 years of experience
New Milford, CT, 06776

About: Growing up, I had a Lab and then a Boxer and two cats. I've also helped my aunt at the doggie daycare she runs out of her home where she often has more than 10 dogs at a time. Everything from a Great Pyrenees to German Shepherds to Doodles to Yorkies. And it's always so much fun! The care I'll give your pets will really depend on them and their needs. There's a very large unfenced grass area behind my apartment building that would be perfect for walks or play. And there are multiple parks in the area too we could explore. At yours, I'd keep whatever their normal routine is. Whether that's taking walks, throwing the ball or just sitting and chilling and scratching butts. Their butts of course! There's a very large unfenced grass area behind my apartment building that would be perfect for walks or for play. And there are multiple parks in the area too. At yours, it depends what you need. We could take walks, throw the ball or just sit and chill and scratch butts. Their butts of course!

Sitter Profile Image: Liliana N.
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Liliana N.
from
$16
per walk
7 years of experience
New Milford, CT, 06776

About: I take care of animals feeding them,cleaning after them cleaning litter boxes,socializing with them making sure they taking care of with extra love like they deserve I am working part time at shop rite two days a week so I am available anytime on my days off or after work I have open available I get my work scheduled every thursday two days advance before I planned anything for next week I would ask their owners how much food they should eat or if they are on restricted diet same for medications I would always ask them that before I do anything make sure I get the important details in first so I know what to do and what to expect ,I feed my cats Iam’s,play with them,hold them in my arms give them their morning pets and give their bedtime treats at 9:00 they already it and they are all lined up before I get in the kitchen .

Sitter Profile Image: Margaret S.
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Margaret S.
from
$20
per walk
5.0 out of 5 stars
11 reviews
2 repeat clients
17 years of experience
Wappingers Falls, NY, 12590

Extremely pleasant,personable and professional. A definite keeper!

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Ray R.
Sitter Profile Image: Samantha M.
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Samantha M.
from
$75
per walk
5.0 out of 5 stars
25 reviews
5 repeat clients
15 years of experience
Dover Plains, NY, 12522

About: Choosing a sitter is about more than just a check-in; it’s about finding a calm, capable environment where your pet feels truly understood. My background in healthcare naturally informs how I care for animals—I tend to be an observant caregiver, keeping a watchful eye on comfort levels and the small details that matter for a pet’s well-being. As a working-from-home mom, my days are rooted in a reliable routine. This allows me to provide the consistent, low-stress supervision that is so helpful for all animals who need a little extra help and those who require a patient, intuitive touch to feel at home. I have experience caring for a wide range of needs and species—from the high energy of puppies to the quiet companionship of seniors, the unique needs of rescues, and even farm friends like chickens. Whether it's keeping a medication schedule on track, assisting with mobility challenges, or simply providing a quiet space for a nervous soul to decompress, I focus on creating a safe, gentle environment where every animal in my care can truly relax. If for some reason (vacations/getaways) we are unavailable it will be marked on the calendar. I do my best to confirm my calendar and availability daily. Our front and back yard is fenced in and we are set back from the road. There is plenty of room to run and play. As for feeding; All dogs and/or cats will be fed separately. This includes treats.

Sitter Profile Image: Jillian A.
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Jillian A.
from
$20
per walk
5 years of experience
Hopewell Junction, NY, 12533

About: As a college student who genuinely loves animals, I bring both enthusiasm and responsibility to every pet I care for. I have experience watching and caring for dogs of different sizes and temperaments, and I’m very comfortable with daily routines like feeding, walking, playtime, and basic grooming. What sets me apart is my patience and attention to each dog’s individual needs—I understand that every pet has their own personality and comfort level. I’m especially attentive to safety and making sure dogs feel comfortable and happy while their owners are away. I can handle energetic dogs who need lots of exercise as well as older dogs who require a gentler approach and extra care. I’m also dependable, communicative, and will keep you updated with photos and messages so you always know your pet is in good hands. As a college student, I have a flexible schedule that allows me to dedicate quality time to pet care. I’m available most weekdays around my classes and have open availability on weekends. I can accommodate morning, afternoon, and evening visits, and I’m happy to work with your schedule to make sure your pet gets consistent care, attention, and companionship. Your pet’s safety and comfort are always my top priorities. In your home, I will follow all care instructions closely, maintain your pet’s normal routine, and ensure a calm, clean, and secure environment. I’m attentive to details like locked doors, safe walking practices, and keeping harmful items out of reach. I also take time to build trust with each pet so they feel relaxed and cared for while you’re away. I will keep you updated regularly so you feel confident your pet is safe and happy.

Sitter Profile Image: Olivia C.
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Olivia C.
from
$20
per walk
8 years of experience
Poughquag, NY, 12570

About: I work at an animal rescue with all different types of dogs. From 4 week old puppies, to 14 year old curmudgeon-y dogs. I am ASPCA certified, and I know how to read a dog’s body language. I have experience and confidence measuring, and administering medications. Making sure that your dog(s) are safe, healthy, fed, and walked are my top priority, and I’m looking forward to meeting your fur babies! I work part time at an animal rescue, and much of my day is empty. I do not work Wednesdays or Thursdays. I have limited availability on Fridays and Saturdays I will respect your pets boundaries, and will always be sure to keep your home clean and comfortable. Your fur baby, home, and belongings will be safe and sound.

Sitter Profile Image: ATHENA M.
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ATHENA M.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
3 reviews
3 repeat clients
18 years of experience
Carmel Hamlet, NY, 10512

Athena was kind and patient with Pebbles!

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Lisa C.
Sitter Profile Image: Harley Mae J.
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Harley Mae J.
from
$35
per walk
5.0 out of 5 stars
4 reviews
3 repeat clients
2 years of experience
Poughquag, NY, 12570

About: I took care of dogs around my neighborhood as a teen. For the past year I’ve been training a psychiatric service dog through my school. He lives with me full time! I am currently a student, so around my classes I have a lot of time to care for pets, especially on weekends. I love making the time to meet new animals and be outdoors. I have experience caring for dogs in my neighborhood and am always sure to leave a house as good or better than I found it.

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

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Sitters in Wingdale average 3
repeat dog walking clients

FAQs for Dog Walking - Wingdale

Frequently asked questions about Rover

The average cost for Dog Walking in Wingdale on Rover is $22.2 per walk (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Walking easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Walking. For more information on service fees, click here .

As of July 2026, there are 1,828 sitters on Rover offering Dog Walking across Wingdale. 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 Wingdale. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.

For dog walking services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Wingdale.

Got specific details you'd like the dog walker to include? Message them in the app before your dog’s 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 Wingdale. On Rover:

  • 93% of walkers can help with special care needs
  • 96% can help with giving oral medications or injections
  • 99% 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 short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker 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. Most pet parents and walkers on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement walker.

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