Dog Sitting New Windsor
Book a New Windsor dog sitter to watch your dog in your sitter’s home or yours.
Over 74 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.
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. I'm a teacher on summer break so my schedule is wide open. I am unavailable on August 9th and from August 14th to the 21st. I am also open to sitting during evenings and weekends or drop-bys during the school year. 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.
“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: I’ve had lots of pet care experience throughout my life, there’s never been a time that I haven’t had pets in the house between cats, dogs, and other small animals. I work from home, so I will be here 24/7 to watch your fur babies (my mama is always around for emergencies). We have a fenced in yard to protect your pets since their safety is my #1 priority. We have a Shipoo named Suzie who would be kept in a separate area unless otherwise discussed. Your pet will ALWAYS be loved and cared for as if they were my own ❤️ 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 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.
“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!”
About: Hi! I’m a college student and lifelong animal lover with over 5 years of experience caring for pets. I currently have two cats and one dog of my own, and I’ve also pet sat for friends and family for the past 5–6 years. Through these experiences, I’ve cared for pets with different personalities, energy levels, and needs. Whether it’s dog walking, feeding, playtime, litter box care, or providing companionship, I make sure every pet feels safe, comfortable, and loved while their owner is away. I understand how important it is to trust someone with your pets, and I treat every animal as if they were my own. I’m responsible, dependable, and committed to providing attentive care and regular updates to pet owners. I have wa flexible schedule and plenty of time to dedicate to pet care. During the summer and school breaks, I have wide availability for walks, drop-in visits, and pet sitting. I do my best to accommodate each pet’s routine and needs, whether that means early morning walks, afternoon playtime, or evening check-ins. I communicate regularly with pet owners and provide updates so they know their pets are happy and well cared for. Your pet’s safety and comfort are my top priorities. I carefully follow all instructions regarding feeding schedules, medications, exercise, and routines. I understand that every pet is different and take the time to make them feel comfortable and secure. When caring for pets in a client’s home, I respect their space and maintain a clean environment. I provide regular updates and photos so owners can feel confident their pets are receiving attentive, loving care while they are away.
“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! ?”
“Finding a new petsitter after moving is tough, but we liked Maryline so much we immediately booked her again after our first booking was complete! She’s reliable and communicative, and most importantly our social little guy has taken an immediate liking to her. I highly recommend Maryline and will definitely be booking with her again in the future!”
About: I have a very special connection with all animals and will love and care for your pet as if it were my own! I have a lifetime of experience with cats and a few years of experience with dogs, namely raising and training my own dog from ~2 months old. He’s the sweetest, happiest pup and he is very loved! I work from home and have plenty of time to spend with your pet, whether that’s walking them, playing with them or bringing them to appointments!! I don’t have a fenced in yard but have plenty of space to walk and play with your dog outside (or inside!). I can crate the dog if necessary, and my puppy is extremely friendly and welcoming with new dogs!
About: Whether we’re talking dogs or cats or hamster or frogs or birds… you name it. My family and I have cared for an abundance of pets throughout life. I now have the sweetest beagle mix aka my best friend Toby! I work 24 hour shifts as an EMT so I am able to cover my full time hours in only two days. This allows the other 5 days to spend time and play with the pups! On my days off you can find me and Toby walking around town or hiking Mnt. Beacon. I have much experience with many types of dogs— different sizes, breeds, strength, temperaments. I can assure you pup is in good hands! : )
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!!
Christina really came through in my time of need. She takes such great care of my Benji and Bailey and even manage to navigate my patio construction with grace and humor expressed through her daily updates. She has taken some of the best pictures of the pups too! Highly highly recommend ⭐️⭐️⭐️⭐️⭐️
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
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying New Windsor sitters!Sitters in New Windsor average 5 repeat dog sitting clients
FAQs for Drop-In Visits - 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 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 2,328 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
- 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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