Dog Sitting Wingdale

Book a Wingdale dog sitter to watch your dog in your sitter’s home or yours.

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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: Rachel F.
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Rachel F.
from
$30
per visit
5.0 out of 5 stars
8 reviews
2 repeat clients
10 years of experience
Amenia, NY, 12501

Rachel was great! Took bery good care of our furry friend and sent lots of pictures. Our house was left in good order as well! Look forward to working with her again!!

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Teresa S.
Sitter Profile Image: Timothy D.
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Timothy D.
from
$22
per visit
5.0 out of 5 stars
1 review
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: Celina I.
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Celina I.
from
$20
per visit
5.0 out of 5 stars
27 reviews
8 repeat clients
6 years of experience
Poughkeepsie, NY, 12603

Celina is so pleasant, my puppy really took to her. I look forward to contracting her services again very soon.

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Ray R.
Sitter Profile Image: Cory M.
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Cory M.
from
$20
per visit
5.0 out of 5 stars
60 reviews
25 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: Rachel O.
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Rachel O.
Star Sitter
from
$40
per visit
5.0 out of 5 stars
53 reviews
24 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: 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: Stacy S.
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Stacy S.
from
$20
per visit
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: Iza P.
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Iza P.
from
$45
per visit
5.0 out of 5 stars
34 reviews
14 repeat clients
20 years of experience
Lagrangeville, NY, 12540

About: Hi my name is Izabela. I have 2 amazing kids and 3 dogs :). I love spending time outside and go for long walks. Teaching my kids all about different breads. We make sure that our home is safe and fun for everyone. I love to send a lot of picture so you can see how is your dog day is going so be prepared here from me a lot 😂 I will love to meet you and you pup :) Few adds to the service : Daycare drop of starting at 7am pick up any time before 6pm after that every hour is $10 extra . Before 7am extra charge too . Overnight stay is 24 hours after that every next hour $10 extra You have to provide food for you dog . If not provide there is extra charge of $5 for each day ( I make my own food and treats ) Thank you for you understanding and we love to meet you :)

Sitter Profile Image: ATHENA M.
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ATHENA M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
4 reviews
5 repeat clients
18 years of experience
Carmel Hamlet, NY, 10512

About: I've been taking care of dogs for over 12 years. And love them like they was family. And I watch all my friends and families dogs. I also work for wag. I have open availability for boarding. My favorite animal is a dog i always wants to be with dogs. ( i use to own cats too incase any feline friends need. I had 4 dogs growing up and as a child it was my job to care for them. When my parents sold the house because of their split they split the dogs

Sitter Profile Image: Jeffrey V.
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Jeffrey V.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
25 reviews
10 repeat clients
4 years of experience
New Fairfield, CT, 06812

Jeffrey took great care of our Samoyed Oakley! He treated him like one of his own and Oakley got to make new friends! Very happy with the daily visits.

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Tyler A.
Sitter Profile Image: Andialisa V.
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Andialisa V.
from
$10
per visit
5.0 out of 5 stars
1 review
3 years of experience
Poughkeepsie, NY, 12603

Andialisa was super nice with Toto and very accommodating of my requests. I’ll definitely love to have them check in on Toto again! Thanks again!

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Liz A.
Sitter Profile Image: Olivia C.
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Olivia C.
from
$18
per visit
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: 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: Zaida A.
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Zaida A.
from
$25
per visit
13 years of experience
Poughkeepsie, NY, 12603

About: I have 2 dogs, Australian Shepperd hound mix and a Chihuahua mix. Previously had a Bichon Frise mix (Rip). I will love your dog just like my own. I can do drop ins, walks or pet sitting. I love sitting on the floor with my own dogs and sing life away (not a very good singer but my dogs loves it) i can do the same for yours. Lol I am available full time. Monday through Friday. Saturdays available at my own discretion. If needed i can make arrangements. Although i love all dogs i could care for small to medium dogs. Life full of dogs is a wonderful beautiful life. I will provide the best care for your baby. They are our children so why not give the best for them. Working from home is boring!! I have availability for your doggie baby Monday through Friday 6pm -10pm and weekends at my own discretion. I will post availability on my calendar. I have 2 friendly dogs, 1 is high energy very playful and chihuahua is very chill. Tell me what you're dog likes and i will always try to work around that.

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: Harley Mae J.
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Harley Mae J.
from
$30
per visit
5.0 out of 5 stars
4 reviews
3 repeat clients
2 years of experience
Poughquag, NY, 12570

Harley is punctual and reliable!

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John L.
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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 July 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 July 2026, there are 1,823 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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