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.
About: I have been Dog and Cat sitting Full Time, I have many 5 star reviews on TrustedHousesitters. I just heard of Rover and am excited to try it. I am friendly, energetic and reliable. Dog sitting has been such a rewarding experience, and I am grateful for this responsibility. I am very blessed to have animal companionship through this service. Pets need the same things we humans do; attention, affection, play, and protection. Thank you for reading and I look forward to the opportunity to provide care for your pet. Their safety and happiness is my priority. I have experience with all personalities and I genuinely love caring for pets and going for walks and hikes and cuddles. I am currently working remotely, I will have plenty of time to care for you pup. Hoping to get to meet wonderful animals her in Portland. I am very neat and organized, I need a clean space to function. I have loads of reviews mentioning how clean I am. I am very patient, and love to go on walks and play.
“This was our first time using Maryline as a pet sitter and she did a great job with our three kitties. My one cat can be stubborn about taking his medication and she was able to persuade him. She was also very response. Would definitely recommend : )”
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!
“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 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.
“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 second time booking with Alexis and I had another great experience! She was communicative, sent great photos, and took great care of my two cats. Thank you Alexis!”
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: Hi I’m Gretchen! I’ve always loved animals and three years ago I got my own dog, the cutest Sunny. Since then I’ve cared for our dog and watched many others. At our house your dog would get at least one long walk a day (a minimum of two miles), excellent attention throughout day (I work from home) a fun home environment (lots of playing) and tons of snuggles. I have an active dog so go on at least one long walk a day and would love to bring your pup with us. I work from my home office so am around all day. I have a very friendly 3 year old Australian Shepard mix that loves to play and hang with other dogs. My 11 year old son also loves to pet dogs and give them tons of attention.
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 will put my best foot forward to make sure you and your dog have the most comfortable experience while having me as a sitter . Typically have to walk my friends dogs when they or out to work recently bin puppy sitting for another figured I could turn it into a gig ! Make sure they get enough food and water and go out for enough walks.Also a bit of play time never hurts any body I always say!
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.
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 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 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 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 2,339 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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