Dog Sitting New Windsor
Book a New Windsor dog sitter to watch your dog in your sitter’s home or yours.
Over 75 pet parents in New Windsor have booked dog sitting
New Windsor, Find top rated dog sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Maryline is a wonderful sitter, she always takes great care of my cat Meowtus and he loves her and her son. She is highly responsive to questions and concerns and replies very quickly. Would definitely recommend!”
About: I’ve walked and trained my own lab mix (10) as well as worked as a dog walker and sitter for independent clients. I’m great with energetic dogs of all sizes. I work a minimum wage job full time during the week, but am looking to supplement or replace it with dog walking on weekends and evenings. At my clients home I will sit out with the dog and crate it easily if needed. I am able to take the dog out every few hours and love taking them on long walks if desired.
“Julia was fantastic. We needed someone to drop in for our chocolate lab while we were away for a softball tournament. I realized he needed two drop ins and she was very accommodating. She was punctual, friendly, and took good care of our boy. Would recommend Julia 🙂”
“Leah took great care of our two cats while we were away. We appreciated the daily photo updates and notes on how the cats were doing. Good communicator and very responsive.”
“Jill is AMAZING! This is the second time that she helps out with Milo and he LOVES her. I appreciate that she sends pictures of her time with him. Will definitely continue to work with Jill!”
“Rebecca was so polite and sweet. Rebecca and piper hit it off great. Instructions were no problem and from what we seen it was great visits , thankyou Rebecca for the help and we hope to have more drop ins in the future.”
About: Hi there.. I have always owned a dog in my life. I have worked at an animal shelter for 2 1/2 years taking care of the dogs. I have been around most breeds and personality types. I am calm and patient around dogs and know how to read their body language. But I also love to be goofy and playful with them when the environment is right. I believe every dog is an individual and what might work for one dog won’t always work for another. I have some dog training under my belt from working with other trainers and taking classes but I’m not certified yet. If you have any questions please don’t hesitate to reach out! I am currently working part time at an animal shelter so I have plenty of time to dedicate to working with your pups! I currently only offer dog walking and stop ins but will eventually start boarding. I currently don’t offer boarding but I will eventually! At a client’s home I’ll make to gather all the details from the owner to ensure an easy transition for both them and their animals. The last thing I want is an owner to worry while they’re away! I’ll treat your animals like they’re my own.
About: Thank you for taking the time to consider me for your pet needs! I’ve grown up with cats and dogs my entire life. I am an absolute animal lover! I currently have two dogs (2 sweet black labs). I enjoy helping dogs stay active through walks, runs, and playtime. Does your furry one like to snuggle? Because that is welcomed too! I have experience caring for dogs from 8 weeks to senior. I also have basic experience with administering oral medications. With me, you can trust that your furry family member is getting excellent compassionate care while you’re away! Please rest assured that your pet will be taken care of. I take pride in being detail-oriented, reliable, and compassionate. Please let me know if I can answer any questions! I look forward to meeting your pet soon! I currently have a very flexible schedule. I am available from early morning until late evening most days. My availability is continually updated to better serve you and your pet(s). I would love to care for your pets in the comfort of their home. I am willing and able to play with them in your yard, walk your neighborhood, etc.
About: Hi, I’m Breyalyn! Professional bellyrub giver, treat dispenser (with permission, of course), and full-time dog lover. As a proud dog mom to my spoiled girl Suzie, I know that dogs aren’t “just pets”, they’re family. Whether your pup loves his zoomies, is a professional squirrel investigator, or a couch potato who wants to nap, I’m happy to match their vibe. We’ll go on exciting walks, play their favorite games, and make sure they get all the love and attention they deserve. When your dog is with me, you can expect: 🐾 Tail-wagging walks and adventures 🎾 Playtime until someone needs a nap (probably me) 💛 Endless love, cuddles, and attention 📸 Plenty of photo updates because I know you’re going to miss them 🏡 Care that’s personalized to your dog’s routine and personality My goal is simple: make your dog feel like they’re on their own little vacation while giving you total peace of mind. So if your pup is looking for a new human friend who will love them almost as much as you do, I’d love to meet you both. Just don’t be surprised if they drag you back to my door next time.. they tend to make themselves at home! 😊😂 I work from home, so I am home ALL day. I love to exercise and we have a fenced in yard for all of the playtime needed (a larger yard for a leashed walk). I’m always open to going for additional longer walks elsewhere Your pet’s safety is always going to be my priority. They will have a separate apartment area of the house (that I spend all of my time in). They will also have a fenced in yard. Food and water (treats if allowed) will be provided all day. My doggie will be kept separate unless otherwise agreed upon!
About: I’ve taken care of dogs my whole life, I have owned and cared for multiple breeds of dogs and cats, big and small, and been a pet sitter for friends and family on and off for the last 10 years. As a result of my experience as a pet parent and sitter I am very comfortable with most breeds. I also have limited experience training full grown dogs as well as puppies. I am available for walks, check-ins, or pet sitting every day. I am also available for boarding on a case by case basis. My work schedule allows me to be present for most of the day, so I can remain attentive and take plenty of walk and play breaks. During the times that I am gone I am able to crate them if that is your preference or they can have free access to the main part of the house and I will check in on them regularly through the doggie cams. I am able to dog sit in your home as well as in my own home, which has a large amount of indoor space that they can roam around in, as well as a partially fenced back yard that they can play in on a long leash with my supervision. I have plenty of time for walks and play breaks during the day. And during the few hours a day that I am out of the house, they can be crated, or they can roam around the main part of the house. I check in on them every half hour through the doggy cams set up in the house. I am comfortable walking, feeding, and if necessary, providing medication on the schedule and in the manner that you prefer.
“Jasmine is fantastic! My dog is nervous around new people and takes a little while to warm up. Jasmine is so patient and accommodating and took the time to make my dog feel comfortable. She’s reliable and communicative and takes great care of my dog when she drops in.”
“This was my first time using Rover and Marie set the bar high. She was very communicative, prompt on her arrivals and followed the instructions we shared with her. My sweet dog looked so happy in all the pictures with her. Will definitely book her again when I’m in the neighborhood.”
About: Hi. My name is Kiki and I love dogs!! I have years of hands-on experience working with dogs of all breeds, sizes, and temperaments. I was a manager at a cage-free dog daycare for 5 years, where I handled everything from group play supervision to administering medications and managing daily care routines. I also volunteered for 3 years at Second Chance Dog Rescue, helping with socialization, walking, and basic training. In addition, I’ve provided trusted pet sitting services in Peekskill, NY for 5 years until the family relocated. I’m trained in pet CPR, comfortable administering all types of medications, and have a dog of my own—so I truly understand how important it is to find someone reliable and compassionate to care for your pets. I have a car, am highly dependable, and treat every animal as if they were my own. Although I work full-time and attend school, I have large daily time blocks available between commitments, which I dedicate to pet sitting, walking, and drop-in visits I care for every pet like my own, ensuring they feel safe, loved, and comfortable while following their regular routine, my skills are administering medications, and giving personalized attention. Every pet has a specific personality so I try to respect that much like people.
About: I have been pet sitting since the age of 14. I have looked after animals of all kinds, such as dogs, cats, chickens, reptiles, and amphibians. I am comfortable giving medication (outside of injection) and am willing to work with animals of all ages. As we enter the school year I am unavailable for midday drop ins but am available for house sitting or walks after 4pm. This is not my full time position so I will be unavailable from 8am to 4pm. My availability will open up during holiday breaks so keep an eye out for when my availability opens up. I always schedule a meet-and-greet before any care to get to know you and your pets. It helps me ensure I am providing the best care.
About: I’m a dedicated animal lover with two dogs and a cat of my own who are truly my children—so I will treat your pets with the same love, care, and attention I give mine. I understand how important it is to leave your pets with someone you trust, and I take that responsibility seriously. I’m patient, attentive, and committed to keeping pets comfortable, safe, and happy while maintaining their normal routines. Whether it’s walks, playtime, feedings, medications, or plenty of cuddles, I make sure every pet feels at home and well cared for. I follow all instructions closely and provide regular updates and photos so you can feel at ease while you’re away. My goal is to give you peace of mind and ensure your pets feel loved every step of the way. I’d love to meet you and your furry family members! I am very active and love going for walks so if it includes your fur baby that’s a plus! I am here to fit your fur babies needs. I love bonding with ALL animals. I have a horse, a cat and two dogs of my own who I love and care for daily. I love giving treats, baths and lots of play time.
“Kaitlyn was an awesome sitter for my cat for the 5 days I was away. She followed all of my instructions that I had and was great with the details and pics of her visits. I would 100% recommend her services. Thank you so much Kaitlyn for taking care of my fur baby! ?”
About: Hello, I’ve had a dog for as long as I can remember. our “foster-fail” pup is learning to communicate with Fluent Pet buttons! She’s the friendliest little Morkie who would love some friends while mom’s home! She’s learned hand signals and verbal commands all with positive reinforcement! Feel free to reach out with any questions at all I work from home and already have a pet care routine built in! We go for three walks a day and whatever time in between we spend in the backyard playing fetch or dipping into her mini pool to cool off We currently have a yard, though it’s not fenced is large and set back. we also have set it up with leads for 50 yards. Our home has a crate and pen area “doggie room” id like to call it just next to my desk where I work if crating / alone time is needed. Three walks a day! The honest kitchen is the dog food we use along side fruits, treats, and peanut butter for snacks! Endless toys and enrichment ideas are planned for every day! Rolled towels for treats, boxes for tearing, snuffle mats, lick mats, balls you name it lol! Athena is pretty spoiled and I’d love to spoil your pup too! She gets along very well with friends and has both female, male, toy sized friends, xl golden doodle friends! She LOVE tugging with other dogs it’s the cutest. Going to someone else’s home would be lovely and I’m happy to bring items with me! Just let me know your boundaries and what you’re working on with your pup and I’m happy to help in any way. Older pups are my sweet spot. My late shihtzu diagnosed with cancer was on medication for a bit and needed a lot of extra love and support, happy to provide this as well.
The median cost per visit for dog sitting in New Windsor is $25
Dog parents share their Rover experiences - New Windsor
Maya was very sweet and communicative. She was able to pick up our last minute drop in request and was very flexible with our schedule/any changes to the selected times. She stopped by, cleaned up after him, walked, fed and gave him fresh water before leaving him with a treat. She also followed our instructions on how to close his gate properly. Much appreciated!!
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.
Meet local sitters who will treat your dogs like family
1. Search
Browse profiles of sitters near you who offer dog sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
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Popular requests for dog sitting - New Windsor
Select a filter and find qualifying sitters offering dog sitting.Sitters in New Windsor average 5 repeat dog sitting clients
FAQs for Dog Sitting - New Windsor
Frequently asked questions about Rover
The average cost for Dog Sitting in New Windsor on Rover is $22.2 per visit (as of September 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 September 2026, there are 2,298 sitters on Rover offering Dog Sitting across New Windsor. 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 New Windsor 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 New Windsor 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 New Windsor 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 New Windsor. On Rover:
- 93% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 97% 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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