Dog Sitting Ossining
Book a Ossining dog sitter to watch your dog in your sitter’s home or yours.
Over 94 pet parents in Ossining have booked dog sitting
Ossining, 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: Surrounded by doggy siblings growing up and now as an auntie to my nieces and nephews, I love to care for your furry children! Your pets will be in great hands. I currently work in a hybrid schedule at my 9-5. I enjoy caring for doggy friends on the weekends and before and after work when needed. I am constantly on top of making sure pets feel at home and comfortable in a new space. I will also make sure pets feel safe and loved when in their own space.
About: I’ve grown up with dogs, and have a lot of experience with training, guided leash walking, and reactivity. I’ve cared for my five-year-old golden retriever since her puppyhood, and have gained a lot of experience walking with, trust-gaining, and loving on an anxious pup. I’m a proud new mom of a human, but my Moosie will always be my first born baby! I’d love to get to know and care for your pup, too :)! I am a school teacher, so I am pretty flexible on hours during the summer. Generally, I am available as follows: Monday- Friday: 10:00 am-7pm. I have a lot of experience walking dogs of all shapes, sizes, and strengths. My own dog is rather reactive, so I like to use walks as fun obedience training opportunities for pups! I find it makes the walk more interactive and bonding, while burning some extra brain energy for our furry friends. I personally appreciate when our walkers play with our girl and give her extra pets before and after walks, and I intend to do the same for yours as well! I will always respect your space and privacy.
“Martin was amazing with my two dogs. He spent the time to built their trust and love and took them on long and engaging walks which left them exhausted. I 100% recommend him.”
About: I’ve taken care of multiple dogs snd cats in my home as a side passion. I love animals and will care for your pet as if it were my own with safety, care, and match their preferences. Petting sitting is a part time passion I do to fill my love for animals. I work from home and am able to board your pet on the weekends or during the week with advance notice. I love to cuddle, pet, play and walk them. I have a pet free home with a large fenced in yard. I also love hiking and walking so I do walks with pets to provide attention and stimulation.
About: I grew up in a big family with lots of pets including dogs, cats, rodents, and birds. I have been successful in self-taught basic training of dogs. I am a graduate student who plans to have pet care be a source of income that fits around my schedule. I have classes during the week and currently live on campus which is why I cannot provide care in my home. I have owned many pets in my life and have cared for different ages from puppies and kittens to seniors. I enjoy promoting enrichment activities and physical exercise.
About: Growing up with dogs taught me something early: pets are family. Outside of my full-time remote tech consulting gig, I provide high-touch based pet care for families throughout Westchester and Manhattan. My goal is simple: create a calm, trusted second home where your dog feels genuinely safe and loved. I intentionally keep bookings limited so every dog receives individualized attention, consistency, and companionship. Whether your pup is energetic and playful, senior, recovering from surgery, or simply loves a calm environment, I tailor care around their exact routine and personality. What makes Kristine different: ✓ 100% work-from-home flexibility ✓ Fenced backyard + Hudson River walks ✓ Real-time photo/video updates ✓ Pick-up/drop-off assistance available ✓ Medication administration experience ✓ Senior & post-surgery support ✓ Calm, low-volume household ✓ Overnight house sitting with light home care included For pet parents who home-cook meals, I’m also happy to prepare fresh dog meals in my home using your provided ingredients. For house sitting clients, I believe premium service should feel complete. In addition to caring for your pet, I help maintain peace of mind by bringing in packages/mail, taking out trash, watering plants, and keeping your home tidy. I’m building long-term relationships with both dogs and their owners. Many of my clients become repeat families, and that trust means everything to me. Let’s schedule a meet & greet and see if we’re a great fit for each other. 🤍 My work-from-home schedule provides complete flexibility for boarding, house sitting, walks, feeding, and bathing. I have my own vehicle to help with pick-ups and drop-offs. My home has a fenced backyard, and located close to the Hudson River, offering safe outdoor access and scenic trail walks. For house sitting, I maintain your pet's exact routine in their familiar environment while also helping collect mail/packages, watering plants, and light cleaning to ensure you return to a tidy home.
“Joseph always goes above and beyond as a pet sitter. He is an incredibly good communicator and I know that my dog is being well loved and taken care of under Joseph’s care. My dog is very active and still has lots of puppy energy, but Joseph remains patient with him and makes sure that my dog can safely get his energy out.”
About: I have been around dogs my entire life! My family dog of 12 years passed away last year, but she definitely taught me a lot. I have experience with dogs of all ages, even senior dogs! I am a recent college graduate (Bucknell University Class of 2024!) taking a gap year before pursuing a master's degree. This means my schedule for the time being is incredibly flexible, and I can help accommodate to your scheduling needs! I happily follow all instructions left for your pet care, and am happy to send consistent updates about your pets well-being! Whatever makes you most comfortable in your home!
“Klaudia was such an amazing Rover! She was so responsive and helped us out in a pinch. Our dog loved her and she made sure to keep us updated every time she checked in on him. Can’t recommend her enough. We absolutely plan to use her again!”
About: Animals are a central part of my life and always have been. I’ve cared for everything from dogs and cats and more, and I truly treat every animal like my own. I understand how stressful it can feel to leave your dog with someone else, so I focus on providing attentive, loving care you can fully trust. P.S. I have a soft spot for snuggly pups and love long walks. I am currently an online college student with a very light course-load! So I have lots of flexibly and time to care for your pup! I have a fully fenced( with the exception of the driveway entrance- which can be fenced off while your pup plays outside) two acre property with 8ft deer fencing. I have two 60ish pound dogs who are very friendly and low key. Our dogs free roam the house yours can as well or can be in a crate if your prefer. We are pretty active and love to go on long sniffari walks!
“Georgina was amazing ! She took care of my cat on short notice and she communicated with me right away to confirm she was available and during the days I was away. My cat can be a little difficult with strangers but Georgina was able to feed her and spend time everyday! Thank you!”
About: I’ve grown up with animals my whole life and genuinely enjoy caring for them. I currently have two cats of my own, including one with a heart condition, so I’m very comfortable administering medications and following detailed care routines. Giving medication twice a day is already part of my daily life, and I understand how important consistency and attention to detail are. I also regularly care for my neighbor’s dog, who requires medication, as well as my sister’s cats, dogs, and rabbits. Through this experience, I’ve become confident handling pets with a wide range of needs, personalities, and energy levels. Whether your pet needs extra patience, playtime, or specialized care, I’m someone who will treat them like my own and make sure they feel safe, comfortable, and well cared for while you’re away! I am available anytime before 7:00 am and anytime after 4:00 M-F. I am flexible during the weekends and can be available all day. I have an apartment in walkable Sleepy Hollow that is scattered with parks for you pets to explore. Additionally, I have friendly cats to help exercise and engaged your pets during the day.
About: I know how to care for dogs and cats alike based upon decades of experience with my own and relatives animals. I can keep up with the most active doggies. I work part-time and have the afternoons free to fill my schedule with pet care. I have flexibility if necessary and could include weekends at times. Your pet's well being is my first consideration. I know the signs of pets that are upset or not feeling well, and I try to keep everyone as happy as possible.
About: I provide calm, one-on-one care for dogs who do best with consistency, close supervision, and a peaceful home environment. I have hands-on ASPCA volunteer experience and 15 years caring for my own dog, Peggy, and I’m especially comfortable supporting dogs with medical needs, anxiety, or those who require extra patience and structure. Because I work from home, I’m able to provide consistent supervision throughout the day rather than leaving your dog alone for long stretches. I follow routines closely, including meals, medications, potty breaks, and rest, while maintaining a predictable environment that helps your dog settle quickly and feel secure. Safety, structure, and clear communication guide everything I do. I provide a calm, clean, and well-supervised environment where your dog is closely monitored at all times and never left unattended.
“5 stars isn’t enough! Emily left very detailed notes and lots of photos. Both of my cats loved her, she has a calming presence that made them feel safe (even my normally scared/skiddish cat). She was able to give him his medicine easily which was the biggest relief while being away from home. She took amazing care of my home, she brought in my packages, cleaned the litter box and vacuumed the litter on the floor. Thank you Emily!!!”
About: For almost all of my life I have had either beloved cats or dogs. I can do long walks or cat playtime. I am also an animal advocate. My small dog with a big friendly personality, who recently passed at age 14, was epileptic and I kept her close. We were besties. I got to spend a lot of time with other dogs with her. Before that I always had cats, I get them, and I find them all cute and hilarious. I have a flexible schedule, mornings are best, right now Mon-wed.. Can take a long walk or just hang out with your animal. Weekends are great. I live in Somers and work part time in Pleasantville. So anywhere in between is great. Will not be caring for dogs in my home at this time, unless very small/tiny and quiet. I can come to your house happy to travel if for a longer stay.
“Doris was great! Very professional and experienced, and kept us updated throughout her check-in/walk. We felt very comfortable having Olive in her care, and we look forward to her looking after Olive again in the future!”
About: My family has had big dogs our entire lives so I learned to take care of them from a young age. I love all kinds of animals! I work from home with a very flexible schedule so I can generally make most times work :) Happy to work around any schedule if needed! It’s definitely a priority to keep your dogs safe during a walk or a visit - my full focus and attention is on them 100% of the time!
About: I grew up in Oklahoma on 90 acres with cows, horses, cats, and dogs. I've always had a passion for animals and the outdoors. One of the unique experiences I offer is adventure outings for your pup. Living near the beach allows me to provide refreshing beach walks, and as an avid hiker, I also enjoy taking dogs on scenic trail adventures where they can safely explore and enjoy nature. I currently have two dogs of my own—a Miniature Dachshund and a German Shepherd mix we rescued. If your dog would benefit from a positive, supervised social outing, I’m happy to provide that as well. Growing up, I regularly cared for and walked neighbors’ and family members’ pets, so I understand how important it is to find someone you trust. My goal is to give you peace of mind while your pet has a fun, enriching experience. You can rest assured that your furry family members will be cared for and loved as if they were my own. As a full-time dog dad to my two pups, I maintain a flexible schedule and am readily available to help ensure your pets receive the care and attention they deserve. Whether it’s a quick neighborhood walk for exercise or an extended stay with a pet who needs a little extra companionship, I’m here to provide dependable, attentive care. My goal is to give you peace of mind while you’re away, knowing your pets are safe, happy, and fully cared for. I am committed to providing a high level of personalized care and attention to every client. I ensure that when you book a walk or service with me, your pets receive my full, undivided focus. This dedicated one-on-one time allows me to tailor each visit to your pet’s individual needs, personality, and routine. I also have a spacious SUV available for safe transportation if needed. For dogs who enjoy a little extra adventure, I offer nature hikes as an additional service, giving them the opportunity to explore and exercise in a safe, supervised environment. Feel free to send me a message with what you’re looking for, and I’ll respond as soon as possible. I look forward to connecting with you and your pets!
The median cost per visit for dog sitting in Ossining is $25
Dog parents share their Rover experiences - Ossining
Brandon took care of Rocky like he was his own! Great service all around. Trust worthy, friendly, respectful and honest. Always gave great feedback and pictures of the daily walks. All around great to work with and I’ll be contacting him again in the near future
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?
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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
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Popular requests for dog sitting - Ossining
Select a filter and find qualifying sitters offering dog sitting.Sitters in Ossining average 6 repeat dog sitting clients
FAQs for Dog Sitting - Ossining
Frequently asked questions about Rover
The average cost for Dog Sitting in Ossining 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 23,750 sitters on Rover offering Dog Sitting across Ossining. 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 Ossining 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 Ossining 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 Ossining 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 Ossining. On Rover:
- 88% of sitters can help with special care needs
- 92% can help with giving oral medications or injections
- 96% 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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