Dog Sitting Wingdale

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

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Sitter Profile Image: Ebony G.
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Ebony G.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
14 reviews
3 repeat clients
25 years of experience
Poughkeepsie, NY, 12601

Ebony is a lifesaver!!! Took care of our four pets for 3 days super super last minute — she is super communicative, sends pictures often, and took our dogs on a walk daily. I have a kitten and she took special care of him. Took extra time to make sure each pet felt comfy with her. She’s our go-to sitter now!

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Sarah F.
Sitter Profile Image: Timothy D.
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Timothy D.
from
$22
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
20 years of experience
Arlington, NY, 12603

Timothy was a great sitter for our elderly cat. He was patient, kind and easily administered medication for our fur guy. We absolutely will hire Timothy again when we’re out of town and know our cat Stoopy would be in good hands.

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Lauren K.
Sitter Profile Image: Cory M.
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Cory M.
from
$20
per visit
5.0 out of 5 stars
60 reviews
26 repeat clients
22 years of experience
Wappingers falls, NY, 12590

About: Hi my name is Cory! I love dogs and they seem to know it right away. I have been around dogs since I was 4 years old. I have owned 2 akitas and an English bulldog . My latest Akita Diablo passed away 5 years ago and I haven't gotten another dog since his passing so currently I have no dogs. I only have chinchillas and a hamster as of now. I have a lot of experience working with dogs and they seem to feel relaxed and comfortable when in my care, making this the perfect job for me. I know how to approach these animals in a way that is non-threatening to reduce their anxiety and to help them relax. I can help to maintain the routine they are used to, so they will not get anxious or feel so alone while their owners are away. I have extensive knowledge concerning the different breeds of dogs and I know how to take care of them properly. I understand that some breeds have special needs and that the age of the dog will play a major role in how to take care of them. You can depend on me to provide excellent service and to take great care of your dog/dogs. I know what questions to ask to make sure I understand their specific needs. I will be full time dedicated to your furry child, providing walks and play time as much as needed! There is nothing I wouldn't do to make your dog feel comfortable and keep their schedule to your liking. Please provide a list with your dog's habits so I can make sure they feel at home. Don't hesitate to contact me, I am very flexible with my time, and I will love and care for your dog as my own. I'm currently off from work during the summer and during the school year I only work part time at an elementary school down the road from me (2 1/2 hrs) , So I'll have plenty of time to play with your pups! I will do anything to make your pup feel comfortable and at home away from home during his stay with me. I love detailed instructions so please feel free to let me know everything about your pet! I have a fenced in yard and 2 children who are huge dog lovers who would love to keep your dog(s) busy and keep them company!

Sitter Profile Image: Karif & Natalie J.
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Karif & Natalie J.
from
$18
per visit
30 years of experience
Poughkeepsie, NY, 12603

About: I’ve been a dog lover all my life , currently have five little dogs of my own so when your dog visits he will always have playmates I currently work from home so availability won’t be a problem , my wife also works from home as well, your pets will always be supervised My yard is fully fenced in an of course there will be several playmates to accompany them on there outdoor excursions, I have crates available

Sitter Profile Image: Courtney C.
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Courtney C.
from
$35
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
20 years of experience
Brewster, NY, 10509

She is amazing and takes full care of your fur babies! Recommend 10/10!

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Solomon P.
Sitter Profile Image: Rachel O.
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Rachel O.
Star Sitter
from
$40
per visit
5.0 out of 5 stars
57 reviews
26 repeat clients
20 years of experience
Bethel, CT, 06801

Rachel was really responsive and helped us feel comfortable since it was our first time using a dog sitter/walker. She came to our house twice while we were away and took our pup for long walks and gave him attention. The cat even came out for some pets. Lots of pics were taken which helped my stress level. We would definitely use Rachel again.

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Michelle C.
Sitter Profile Image: Alesandra P.
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Alesandra P.
from
$50
per visit
5.0 out of 5 stars
13 reviews
3 repeat clients
5 years of experience
Poughkeepsie, NY, 12601

About: I grew up around animals, from birds and hermit crabs to cats and dogs, my household has always been filled with pets. I have also fostered medically fragile dogs and volunteered at the Westchester Humane Society. I am passionate about ensuring all animals receive the best possible care and I will give your pet the same love I give my own. I currently work part time and I’m a full time grad student, but I have my own transportation so my schedule is open and flexible. I will schedule a meet and greet with you and your pet to learn all about their unique quirks, likes, dislikes, and routines prior to beginning services with them. I ensure a safe environment by using non-retractable leashes on walks and will send you updates while I am with your pet. Your pet's safety is my top priority.

Sitter Profile Image: Gabriela G.
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Gabriela G.
from
$36
per visit
5.0 out of 5 stars
6 reviews
2 repeat clients
10 years of experience
Danury, CT, 06811

About: I’ve been caring for my own dogs as well as pets of family and friends since a young age, and I understand how important it is to find someone you can trust. I treat every pet as if they were my own—ensuring they feel safe, loved, and well cared for while you’re away. My dog is friendly, well-socialized, and enjoys playing with other pets. With your permission, I’m also happy to provide high-quality photos during each visit, so you can see your pet happy and content. I currently work full-time in a hybrid position, which means I’m home about 3 out of 5 weekdays. I’m also available most weekends and enjoy spending time outdoors. During the warmer months, I often take my dog to the dog park for play and exercise. Your pet will receive plenty of attention, care, and companionship, whether we're relaxing at home or enjoying time outside. I do my best to ensure each pet feels safe, happy, and part of the family during their stay. I have an open, unfenced yard, so for safety, all pets will be leashed while outside. We also have a spacious deck where your pet can relax and enjoy the summer breeze. Inside the home, your pet will be free to roam and play under supervision. My own dog is friendly and happy to provide companionship if your pet enjoys socializing. I have a medium-sized crate available if needed, and plenty of toys to keep your pet engaged. Fresh water will always be available, and your pet’s comfort and safety are my top priorities.

Sitter Profile Image: Jillian A.
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Jillian A.
from
$25
per visit
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: Bianca W.
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Bianca W.
from
$25
per visit
5 years of experience
12590

About: Hi! I'm so glad you're here! I know how important it is to find someone you can completely trust with your pet and that's exactly the kind of care I strive to provide. Whether your pup needs a fun walk to burn off energy or they just want a friendly face while you're away, I'll make sure they feel safe, loved, and cared for every step of the way. I treat every pet as if they were my own, following their routine closely so they stay comfortable and stress-free. I have five years of experience with both my own and family members' dogs, giving me hands-on experience with daily walks, feeding, playtime, and providing lots of love and attention. You can expect dependable communication, plenty of photo updates, and personalized care based on your pet's unique personality and needs. I know every animal is different, and I take the time to earn their trust while making sure you have complete peace of mind. I currently work part-time, giving me flexibility for dog walks and drop-in visits throughout the week. I'd love the opportunity to meet you and your furry family member! Your pet's safety and well-being are always my top priorities. I understand that every pet has their own routine, personality, and needs, so I'll take the time to follow your care instructions carefully and make sure they feel comfortable during every visit. Whether we're out for a walk or spending time together at home, I'll provide a calm, caring, and dependable environment while treating your pet and your home with the utmost respect. My goal is to give you peace of mind, knowing your pet is in safe and caring hands. Here are the Services I offer and What to Expect: 30 Minute Dog Walks include a fun stroll around your neighborhood or a nearby trail to give your pup the exercise, fresh air, and mental stimulation they need during the day. 30 Minute Drop-Ins include potty breaks, feeding, playtime, and of course plenty of snuggles to keep your pet happy and comfortable while you’re away.

Sitter Profile Image: Christine A.
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Christine A.
Star Sitter
from
$44
per visit
4.9 out of 5 stars
98 reviews
33 repeat clients
33 years of experience
Stanfordville, Stanfordville, NY, 12581

Christine was not only friendly and helpful but she was understanding of our dog’s breed and gave us such a piece of mind! She went above and beyond making it easy to highly recommend her to anyone looking for someone to watch their pup. Thank you Christine!

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Amanda R.
Sitter Profile Image: Joe C.
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Joe C.
from
$25
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
10 years of experience
Holmes, NY, 12531

About: I am 24 years old and have had dogs my entire life and know how to properly take care of any dog of any size. Even though I am a dog person cats do not bother me. I graduated from Post University in Waterbury, CT. I am very easy going and super easy to work with. You can reach me at just about any time of the day with any questions or concerns. I knew I have always wanted to do something like this but, was not sure exactly where to go. I am Joe and am happy to start helping out. When I am home I am always walking the dogs and also love to throw the ball around and run with both of my dogs. As said previously I walk and play with my pups and they love to run and stay active just like myself and they have a ton of energy.

Sitter Profile Image: Devon G.
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Devon G.
from
$25
per visit
10 years of experience
Carmel, NY, 10512

About: If you’re looking for someone to just drop a bowl of kibble and scroll on their phone, I’m probably not your person. But if you want someone who will treat your pet like a misunderstood genius or a retired diplomat, we’re going to get along great! I work for the MTA as a train operator in the city, but on my days off I love taking my corgi Zuko on long walks and playing in our yard. I've had dogs and cats since I was young, and have a special affinity for all animals. If you want your fur baby treated like the king or queen they know they are while you're away, look no further! I am currently off Mondays, Tuesdays, and Wednesdays so I will have the full 24 hours of those days to walk, play, entertain, and care for your pets. I have a large unfenced yard on a very quiet street off the main road. I also have a extremely friendly and energetic corgi named Zuko who will assuredly be your pets new best friend. There will be tons of playing, running, fetch and more to ensure your pet has the best experience staying at their home away from home.

Sitter Profile Image: Joseph M.
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Joseph M.
from
$25
per visit
1.0 out of 5 stars
4 reviews
10 years of experience
Danbury, CT, 06811

About: I have been taken care of animals since I’m 25 dogs and cats me and my wife love Animals we have French bulldogs and 2 cats I work full time but have a lot of spare time and looking to do something I love which is taken care of peoples animals Walk my dogs and have a big yard I take them out in to play and run around so I’m always with my dogs and cats

Sitter Profile Image: Denise S.
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Denise S.
from
$32
per visit
40 years of experience
Brewster, NY, 10509

About: I’ve been dog and cat sitting all my life. I also fostered a mid-size mixed terrier. I have two cats of my own. I love how all animals have amazing personalities! I can do dog walking, cat check ins with waste clean-up or over nights which ever you may need. I know how to administer meds to both cats and dogs. It is so important to have your furry loved ones pampered while you are away! I am retired so my availability is flexible. I also enjoy sending photos of your four legged loved one while you are away! I have also watched chickens, turtles, guinea pigs, snakes and iguanas. Looking forward to hearing from you! I am retired so I have a flexible schedule! I can go during the day or stay overnight at your home. Whichever you feel most comfortable with would work! When I come to your house, besides walking/feeding, I do waste cleanup as well. Of course, playing is a must! I will definitely send photos and videos so you know how your furry family member is feeling!

Sitter Profile Image: Sabrina W.
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Sabrina W.
from
$40
per visit
4.6 out of 5 stars
7 reviews
2 repeat clients
20 years of experience
New Milford, CT, 06776

Sabrina is terrific. Very communicative and has made a friend with my grumpy cat, which isn't easy! Definite recommend.

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Russell M.
Sitter Profile Image: Becci S.
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Becci S.
from
$22
per visit
10 years of experience
Patterson, NY, 12563

About: I have experience caring for both dogs and cats and have worked in an animal hospital, where I gained hands-on experience safely handling pets, walking dogs, assisting with their care, and working with animals of different sizes, ages, and personalities. I've also cared for pets for friends, family, and neighbors over the years. Whether your pet needs feeding, fresh water, litter box cleaning, walks, playtime, or simply some extra love and attention, I'm happy to help. I'm dependable, patient, and detail-oriented, and I understand how important it is to follow your pet's routine exactly as instructed. I'll provide photo and text updates during every visit so you can enjoy your time away knowing your pet is safe, happy, and well cared for. I treat every pet as if they were my own. Pet care fits easily into my weekly routine, allowing me to provide dependable and consistent visits. Whether your pet needs a morning check-in, a midday visit, or evening care, I’ll do my best to accommodate your schedule. I understand how important routine is for pets, and I’m committed to providing reliable care and giving each visit the time and attention your pet deserves. I understand that trusting someone with your pet and your home is a big decision. During every visit, I’ll carefully follow your pet’s routine, make sure they have fresh food and water, provide walks or playtime as needed, clean litter boxes or pick up after your dog, and spend quality time with them so they feel comfortable while you’re away. I’ll also send photo and text updates after each visit so you always know how your pet is doing. I treat every home with respect and every pet with the same care and attention I give my own.

Sitter Profile Image: Nichole F.
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Nichole F.
from
$25
per visit
4.9 out of 5 stars
12 reviews
4 repeat clients
9 years of experience
Wappingers Falls, NY, 12590

Nichole was amazing! We’ve had a several drop-ins with her to feed/check on our 4 year old calico cat. She always follows instructions perfectly and is very responsible. Our cat is usually shy around strangers, but has come out a few times for Nichole. She was so nice to snap a few pics for us. I highly recommend Nichole for any of your pet care needs!

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Amy S.
Sitter Profile Image: Luke E.
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Luke E.
from
$15
per visit
30 years of experience
Danbury, CT, 06810

About: I’ve been around dogs and cats since I could walk, so caring for animals has always felt second nature. I also volunteer as a dog walker, socializer, and trainer at Danbury Animal Welfare Society, where I work with dogs of different temperaments, energy levels, and needs. My style is calm, patient, and attentive, whether your dog needs a real exercise walk, your cat needs a quiet check-in, or your older pet just needs someone gentle and consistent. I know trusting someone with your pet and your home is a big deal, so I take reliability seriously. I’ll show up when I say I will, pay attention to your pet’s routine, and send clear updates so you know they’re safe, happy, and cared for. I currently work full time, but my evenings and weekends are often free. I’m a good fit for weekend walks, evening check-ins, drop-in visits, and occasional pet care when your regular routine needs extra support. Because I value reliability, I only accept bookings I know I can show up for fully and on time. I pay close attention to each pet’s body language, comfort level, routines, and boundaries, and I never force interactions with people, dogs, or unfamiliar situations. For walks, I keep dogs securely leashed, avoid unsafe areas, and adjust the pace to the dog’s age, energy, and temperament. I’m comfortable with shy, anxious, energetic, and older pets, and I believe patience and consistency go a long way. For drop-ins, I’ll respect your home, follow your instructions carefully, check food, water, litter, doors, and gates, and send clear updates so you know how your pet is doing.

Sitter Profile Image: Nadia F.
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Nadia F.
from
$20
per visit
5.0 out of 5 stars
9 reviews
3 repeat clients
12 years of experience
Poughkeepsie, NY, 12603

About: Hey! My name is Nadia Figueroa. I’ve been working with Dogs for 12 years as a supervisor in a dog daycare and a dogwalker, it’s something I enjoy doing as it gets me outside enjoying my surrounding, while having great company with a puppy pal. I feel like I can offer more than most as I can work with your routine and teach basic training, I can administer meds and do any feeding and lighthouse work, such as grabbing mail, watering plants etc. when your dog is with me there is always love at both ends of the leash ❤️. I can never replace you, but I can ease them missing you while your away! I hope to meet some Amazing Dogs and thier owners! I’m a stay at home mom who works part time at an animal rescue & sanctuary in the evening so my days are very flexible My yard will be fenced in soon and I have 2 friendly doggos that love new company to play with! I also have a separate area if your dog would feel more comfortable without any other dogs for boarding

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The median cost per visit for dog sitting in Wingdale is $25

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Sitters in Wingdale average 5
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FAQs for Drop-In Visits - Wingdale

Frequently asked questions about Rover

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

Rover makes budgeting the cost of Dog Sitting 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 Sitting. For more information on service fees, click here .

As of August 2026, there are 1,802 sitters on Rover offering Dog Sitting across Wingdale. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Wingdale stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Wingdale choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

Every sitter 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 .

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.

A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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 sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters 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.

While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.

To find sitters in Wingdale with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.

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

  • 94% of sitters can help with special care needs
  • 97% can help with giving oral medications or injections
  • 98% 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.

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 sitter.

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