Dog Sitting in New Windsor
Book a New Windsor dog sitter to watch your dog in your sitter’s home or yours.
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Top rated New Windsor dog sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
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.
About: I have experience with being around animals since I’ve been 5 years old. I have two dogs of my own and three cats as well. I will make sure the animals are comfortable, loved and taken care of properly. I am patient, caring, and have high energy. I am big on play time and walks and making sure they get their exercise for the day. I have walked dogs before and also provided in house care for several of my neighbors and close family friends. I really do enjoy being around animals and find it very relaxing. I’m a college student and can be very stressed at times so getting to play with an animal really is something I look forward to. Thank you (: On a daily basis I am always making sure my animals are fed, getting play time in, cuddles and more! They are so important to me! Making sure my pets always have water and their litter box is clean on a daily basis. I always ensure they get little extra treats throughout the day as well as cuddles!
About: I am the most experienced, cost-effective, and caring pet sitter you will find. I am dedicated to providing worry-free pet care directly in your animal’s home environment. I work a flexible schedule as a barista and am working toward pet sitting full time, so your pet will always be my top priority. I approach every situation with extreme compassion. I assess every possible need and think through every possible outcome from top to bottom. I approach every walk, visit, and task with a mindful, in-the-moment approach.
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! : )
About: Im a loving caring dog lover. Ive fostered dogs for about 8+ years now. If it was up to me id take all the dogs that need families into my home . I want to join this job because its flexible & i get to learn about different dogs and the way they act. Im good with dog training im very big on training with treats and learning how to eat in groups. The cuddles are the best when it comes to bed time. Im very active so im always at the park with my other dogs as well and backyard time mostly requires a pool . Pets are humans they need love equally and thats my motto. Lets get the fun started this summer for good runs and good excercise
“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 always been a dog lover! My fur baby passed when I was 12 so I TRULY know how important all furbabies are. I promise to treat yours with the most care and love as I once did with my own☺️ I have been dog sitting for friends and family member for the past 4 years. I have been successful with teaching some of my past clients simple tricks like sit and shake not because I have been asked but because I just truly like it☺️ I currently work 3 days out of the week as a nanny. Those 3 days I work 8 hour shifts which I completely understand is a lot but with past clients I always make sure that the other days out of the week (that I don’t work) your furbaby will enjoy long walks, car drives, mabey even a little puppychino treat😊 With past clients I’ve always provided pictures for them especially if I take them on little field trips to the dog park or just for a drive☺️
“Abbey was a dream to work with!! Would ten out of ten recommend her and absolutely work with her again :). Our cat Cyrus loved her immediately and she left us detailed updates and photos. She’s super nice, loved Cyrus so much, very prompt and awesome. Thanks again Abbey!!”
“Where do I begin? Mary exceeded all of our expectations. She is extremely sweet, professional, courteous, genuine and responsible. We received txts with updates and photos at every visit to our fur baby. She without a doubt goes above and beyond. Typically, our Shelby takes a day or two to readjust upon our returning with the exception of this time. It was like we had never left! Shelby was so happy and relaxed. We can’t recommend Mary enough and she is definitely our go to from here on out!”
“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: 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!
New Windsor dog parents share their Rover experiences
I cannot say enough good things about Ava as our dog walker. She walks my pitbull, Giovanni, and my Frenchie, Jerry, and is so gentle, patient, and calm with them, which means everything to me. Ava is incredibly reliable, always on time, and treats Giovanni and Jerry like her own. I love the updates I get after walks, and I always feel like they are safe and well cared for when they’re with her. Both dogs are happier, calmer, and get so excited every time Ava shows up. If you’re looking for someone you can completely trust with your dogs—especially strong breeds—Ava is the best!
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 ⭐️⭐️⭐️⭐️⭐️
Popular requests near you
Select a filter and find qualifying New Windsor sitters!How Rover works
1. Search
Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for dog sitting in New Windsor is $25
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 dog sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in New Windsor average 5 repeat dog sitting clients
Dog Sitting FAQs
Frequently asked questions about Rover
Dog sitters on Rover are free to set their rates. The median cost to hire a dog sitter in New Windsor on Rover as of Jun 2026 was about $25 per night, after factoring in Rover’s service fees. A dog sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.
As of Jun 2026, there are 2,357 dog sitters in New Windsor. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, 85% of New Windsor dog sitters respond in under an hour.
Dog sitters in New Windsor have an average of 15 years of experience. Dog sitters with repeat customers have an average of 5 repeat clients. Experience can vary from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in New Windsor.
Rover makes it easy to find New Windsor dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:
- Dogs of all ages and abilities, including puppies
- Dog parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their dog sitter’s pets
There are 2,357 dog sitters in New Windsor on Rover, so you’re sure to find the perfect match for your dog! In New Windsor, 97% of dog sitters offer daily exercise, 94% offer medication administration, and 93% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass background checks for you and your dog’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.
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