Dog Sitting Middletown

Book a Middletown dog sitter to watch your dog in your sitter’s home or yours.

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pet parents in Middletown have booked dog sitting

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Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Joseph & Alexandra F.
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Joseph & Alexandra F.
from
$35
per visit
20 years of experience
Wurtsboro, NY, 12790

About: Originally from upstate NY, I spent time working as a professional veterinary assistant in Atlanta, GA while in school. In this role, I worked directly under a veterinarian to monitor, clean, and provide medical check-ups for dogs at local pet centers, while also providing care for other animals at a boarding and daycare resort. With this hands-on experience, I am deeply familiar with dog health, sanitization, and administering medications. I enjoy spending time with dogs, understand how to spot early signs of illness, and know how to keep dogs on a fun and healthy routine. Since moving back to upstate NY, I do part-time work as a tech consultant from home. This allows me to give plenty of attention to your pet, while also providing plenty of outdoor activities. My wife also works from home, which allows her the flexibility to help as well. Our house is situated right next to the D&H Canal trail, and we take regular walks on a daily basis.Whether your dog is a growing puppy who needs attentive care or an older dog who requires a reliable, experienced handler, my top priority is maintaining their health, safety, and happiness while you are away. My wife and I both work part-time from home, which gives us highly flexible schedules to prioritize your pet's care throughout the week. Our daily routine naturally includes multiple walks along the scenic D&H Canal trail, which directly borders our property. Because our work keeps us at home, guest pets enjoy consistent supervision, frequent potty breaks, and plenty of playful companionship. Our home sits far back from the road at the end of a long driveway, offering a very quiet, safe environment. We sit on 10 acres of land, featuring 3 groomed acres for supervised play and 7 acres of private woods. While our yard is only partially fenced, we have two large, fully enclosed decks that are completely fenced in—perfect for safe sunbathing, lounging, and secure outdoor activities. We also utilize a collapsible fence that we can pull out and set up to create customized secure boundaries if necessary. For exercise, dogs are strictly supervised and kept on-leash as we head down the driveway to our private access point for the D&H Canal trail, keeping them completely away from traffic.

Sitter Profile Image: Nicole S.
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Nicole S.
Star Sitter
from
$40
per visit
5.0 out of 5 stars
52 reviews
7 repeat clients
15 years of experience
Chester, NY, 10918

Nicole did drop ins for my two dogs for a long weekend. She was very attentive and thorough at keeping you informed on how your dogs are doing. We are repeat customers and would highly recommend her!

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Stephanie H.
Sitter Profile Image: James K.
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James K.
from
$30
per visit
10 years of experience
Warwick, NY, 10990

About: Hi, I'm James your new best friend. I am a new dad and dog dad. I have been caring for loved ones pets for years and want to be able to share my love for animals with you all. I have a 1 furry friend "Mocha" but have had lots of experience with dogs, cats and other critters! I'm looking forward to sharing my all my love with your loved ones! I have the ability to care for your loved ones in the evenings and weekends and give them all the love in your absence and more! I choose to not pet sit in my home due having a young child but can happily care for your furry friends in there own home environment

Sitter Profile Image: Sara M.
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Sara M.
from
$30
per visit
5.0 out of 5 stars
26 reviews
7 repeat clients
10 years of experience
Port Jervis, NY, 12771

Sara was awesome! Very informative and kind!

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Marisa S.
Sitter Profile Image: Raquel S.
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Raquel S.
from
$20
per visit
5.0 out of 5 stars
7 reviews
2 repeat clients
20 years of experience
New Hampton, NY, 10958

Raquel was great and very sweet toward my senior pup! Thank you. Would rebook.

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Suzanne T.
Sitter Profile Image: Kim M.
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Kim M.
from
$30
per visit
5.0 out of 5 stars
23 reviews
9 repeat clients
2 years of experience
Port Jervis, NY, 12771

Kim was a great sitter for my special needs cat. She gave him the care and attention he needed and made sure I was updated on whether he’d gone to the bathroom. I also appreciate her willingness to care for him over the holidays - it was a huge help since we could not be home with him!

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Christen D.
Sitter Profile Image: Maddy A.
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Maddy A.
from
$20
per visit
4.9 out of 5 stars
7 reviews
5 repeat clients
7 years of experience
Warwick, NY, 10990

Maddy was great!! Very communicative and super sweet to our kitty. I highly recommend her!

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Dianna & Shea G.
Sitter Profile Image: Robert L.
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Robert L.
from
$35
per visit
5.0 out of 5 stars
7 reviews
1 repeat client
30 years of experience
Warwick, NY, 10990

Robert was a great dog care person! He gave our dogs special attention by interacting with them in play & extra pets and cuddles. Our dogs love Robert. Highly recommend.

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Kimberly A.
Sitter Profile Image: Lizbeth S.
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Lizbeth S.
from
$30
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Slate Hill, NY, 10973

About: Hello! My name is Lizbeth. Pets have been a part of my life since I was young. And throughout those years my family and I have had and cared for several dogs and my own cat. I have experience from caring for puppies to senior dogs with disabilities. I love to spend time with them and look forward to meeting your pet family. I currently have a part time job and l am usually available most mornings and sometimes early afternoons. My schedule varies week by week and is flexible. I am more than happy to adapt to what each client needs/prefers and what each pet is used to. Ultimately to help the family and pet feel comfortable.

Sitter Profile Image: David L.
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David L.
Star Sitter
from
$90
per visit
5.0 out of 5 stars
3 reviews
2 repeat clients
20 years of experience
Middletown, NY, 10940

About: 🎉 Use Promo Code: FAMDRD77423 for $40 OFF your first Rover booking! 🎉 (Valid for first-time Rover users only.) As a physician, I've dedicated my career to caring for others, and I bring that same compassion, patience, and attention to detail to every pet I care for. My medical background has taught me to stay calm under pressure, notice subtle changes, and provide thoughtful, attentive care. Whether your pet is energetic, shy, senior, or has special needs, I'll make sure they feel safe, comfortable, and loved while you're away. I've been caring for dogs since I was about 10 years old, starting by helping neighbors with their pets during vacations and busy schedules. Over the years, I've gained experience with dogs of all breeds, sizes, personalities, and energy levels. From playful puppies to gentle seniors, I tailor my care to each pet's unique needs. I also have experience training dogs using positive reinforcement, consistency, and patience. My goal is always to provide a fun, safe, and enriching experience while reinforcing good behaviors. Experience & Qualifications 👨‍⚕️ Physician with a calm, observant, and compassionate approach 🐾 Over 15 years of hands-on dog care experience 🎓 Experience with positive reinforcement training and basic obedience 🐶 Comfortable with puppies, adult dogs, and senior dogs Specialized Care 💊 Experienced with administering medications and following detailed care instructions 🦴 Comfortable caring for senior and special needs pets 💛 Patient with anxious, shy, or first-time boarding and sitting pets 🏡 Able to maintain your pet's normal routine to reduce stress Flexible Boarding Options 🌳 I offer flexible boarding options in my house or apartment, allowing me to match your pet with the environment where they’ll feel most comfortable. 🛋️ Quieter pets may enjoy a cozy apartment, while more energetic dogs can benefit from extra space to play and relax. 🎯 My goal is to provide the best experience based on your pet’s unique personality and needs. What You Can Expect ❤️ Every pet is treated like a member of my own family 🚶 Walks & playtime based on your dog's personality & energy level 📸 Frequent photo and video updates throughout every visit 📱 Prompt communication and dependable, detail-oriented care 🐾 A safe, loving & low stress environment where your pet can feel comfortable & happy I also have a trusted team of experienced caregivers who may occasionally assist with your pet’s care, providing extra flexibility and reliability. They may help with training, playtime, grooming, enrichment, or whatever else you may request while following the same commitment to safety, communication, and treating your pet like family. My Reliability Promise ✅ Your booking is my commitment. If an unexpected emergency or scheduling conflict prevents me from caring for your pet, I’ll help arrange a trusted replacement sitter so you’re never left scrambling at the last minute. 🐾 Your pet will continue receiving safe, reliable care from someone dependable. 💛 Your pet’s safety, comfort, and your peace of mind are always my top priorities. Whether your pet enjoys long walks, playtime, quiet companionship, or simply sticking to their normal routine, I'll provide the same level of care, kindness, and attention that I would want for my own dogs. I look forward to meeting you and your furry family! Pet care fits easily into my daily routine. I’m an early riser and make time every day for walks, play, and check-ins. My work schedule is flexible, allowing me to plan visits around each pet’s needs—whether it’s morning exercise, midday drop-ins, or evening companionship. Caring for animals is a relaxing and rewarding part of my week. I treat every home and pet with the same respect and care I give my own. I follow your instructions carefully, maintain a clean environment, and keep pets safe with close supervision indoors and secure leashes outdoors. I focus on helping pets feel comfortable and calm, especially when their families are away, so they always feel cared for and at ease.

Sitter Profile Image: Rhylee R.
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Rhylee R.
from
$25
per visit
5.0 out of 5 stars
21 reviews
4 repeat clients
8 years of experience
Montgomery, NY, 12549

Rhylee was thoughtful and kind and took great care of our pets. We are new to the area and needed some last-minute care, and she really came through in a pinch.

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Kait H.
Sitter Profile Image: Emily H.
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Emily H.
from
$18
per visit
4 years of experience
Sussex, NJ, 07054

About: Ive had pets (dogs, cats, fish-oh my!) since I was very young, so I truly understand the meaning of our pets are family. My professional experience comes from the last 5 years as a marine mammal trainer and zookeeper! I have the deepest compassion for animals of all shapes and sizes, from exercise to medical care, to behavioral study…I have done all things animals! I’m currently working part time, so I have ample room in my schedule to come hang with your beloved pet! I am a very active person and would love to take them for walks if that is in their wheelhouse! I have my own sweet old lady Maltese at home, who absolutely adores her own personal space. That being said I am not currently accepting boarding or visits in my own home, but am more than happy to come to yours!

Sitter Profile Image: Michelle C.
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Michelle C.
from
$22
per visit
5.0 out of 5 stars
14 reviews
7 repeat clients
15 years of experience
Wurtsboro, NY, 12790

I appreciate how flexible Michelle is about coming to check in on my cats. I know they don't come out, but it's peace of mind knowing they have someone to look in on them while I'm away.

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Doreen D.
Sitter Profile Image: Shannon & Justin M.
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Shannon & Justin M.
from
$30
per visit
5.0 out of 5 stars
11 reviews
8 repeat clients
20 years of experience
Warwick, NY, 10990

Justin was reliable and got along great with my German Shepherd.

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Leilani W.
Sitter Profile Image: Victoria F.
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Victoria F.
from
$25
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
5 years of experience
Bloomingburg, NY, 12721

Thank you Victoria for taking such good care of scout. I would highly recommend using her as your go to sitter

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Phil C.
Sitter Profile Image: Shelby T.
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Shelby T.
from
$17
per visit
1 year of experience
Westtown, NY, 10998

About: I’ve been certified as a Vet Assistant, I am also currently in school for my license as a Vet Technician. I’m very confident that I will be a safe environment for your furry friends! I’m currently a student so weekends will be more manageable for me, In case of any emergencies of course I can make accommodations during weekdays. I’ve had more than 11 animals my whole life growing up (5 dogs) (4 cats) (2 two fish) I would say I’m extremely experienced in caring for animals. Professionally my experience would be under a year as I am still in school, I live on 67 acres and a large yard which will give your dog enough room to run with the wind and enjoy the fresh air.

Sitter Profile Image: Elizabeth D.
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Elizabeth D.
from
$28
per visit
5.0 out of 5 stars
8 reviews
2 repeat clients
27 years of experience
Chester, NY, 10918

About: I’ve had cats, dogs and many other animals my entire life and know how important it is that they get quality care and love! I have always cared for all other animals with love and attention as if they were my own whether they were strays or belonged to friends/family. I have dog-walked and pet-sat for friends and family whenever they have needed help, making sure their pets are well taken care of not just physically but emotionally (to the best of my ability!) while they are away. I have walked and pet-sat dogs of all kinds including puppies and senior dogs as well as disabled and special needs! I have also done feedings and general care for other animals including chickens, horses, goats, llamas, reptiles and others. Throughout my life I have rescued and/or taken care of a range of animals including kittens/cats, puppies/dogs, rabbits, chickens, raccoons, mice, opossums, birds, fish and reptiles. With many years of experience caring for animals, I am confident in my ability to provide attentive, compassionate care to your fur babies! I am available in the mornings and early afternoons for pet check-ins, walks, and other care needs. Additionally, I am available after 5pm on weekdays for any evening care, ensuring pets receive attention at the end of the day. I also offer overnight or weekend boarding, providing reliable care when owners are away. My flexible schedule allows me to tailor my services to meet the specific needs of pets and their owners, offering peace of mind and dependable support. When boarding pets in my home, I offer a safe and comfortable environment tailored to each pet's needs. Depending on the pet's temperament and preferences, I can either crate them for security or allow them to roam freely in a designated pet-friendly area. I ensure that they have plenty of space to play, rest, and feel at ease. I’m committed to maintaining a routine similar to what they’re used to at home, including feeding schedules, exercise, and personal attention. If needed, I can also provide extra care, such as administering medications or offering special accommodations for senior or special-needs pets. When caring for pets in the client’s home, I focus on maintaining a familiar and safe environment for them. I will follow the established routines for feeding, walking, and any other care instructions provided. Whether it’s keeping them indoors, ensuring they have outdoor playtime, or administering any medications, I approach each task with responsibility and attention to detail. My goal is to offer peace of mind to pet owners, knowing their pets are safe, happy, and well cared for in the comfort of their own home or mine.

Sitter Profile Image: Alexa M.
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Alexa M.
from
$25
per visit
5.0 out of 5 stars
2 reviews
8 years of experience
10916

About: I have grown up with animals my whole life. I have been responsibly taking care of my dogs and cats on a daily basis. I have experience with a variety of dogs at all different ages. I’m also familiar with dogs who need special accommodations for medical conditions. I wholeheartedly love animals and would provide the utmost care to your pets that I would want for my own from a sitter. My schedule changes week to week, but generally I can be available in the morning, afternoon or evenings. Feel free to message about dates you need someone to care for your pet! I have plenty of experience dealing with animals and would want to create a safe environment for them. I would ensure that your pet is happy and cared for to the highest extent of the service. I’m happy to stick around to give your pets extra attention as well!

Sitter Profile Image: Natisha D.
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Natisha D.
from
$100
per visit
4.8 out of 5 stars
77 reviews
36 repeat clients
2 years of experience
Middletown, NY, 10941

Perfect communication and reliability as always!

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Tania L.
Sitter Profile Image: Mekenna H.
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Mekenna H.
from
$50
per visit
5.0 out of 5 stars
11 reviews
8 years of experience
NY, 10916

Mekenna was so helpful in checking on my cats while I was away. The communication prior to, during, and after my trip were all appreciated and left me feeling like my cats were well taken care of. Fully reccomend!

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Christopher R.
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The median cost per visit for dog sitting in Middletown is $25

Dog parents share their Rover experiences - Middletown

1 / 1
5.0 out of 5 stars

Vicky made sure my babies were well taken care of during a drop in visit. They seemed to really like her!

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Shaunna K.
Drop-In Visits
5.0 out of 5 stars

Linda was great especially with my older hound dog. She sent lots of pictures and the dogs had fun with her.

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Don
Drop-In Visits
5.0 out of 5 stars

Jennifer stops by for drop in visits for our senior golden retriever , and we are so lucky to have her coming to our house. Knowing that our dog with someone so caring gave us so much peace of mind. We are grateful for the attention she gives to our pet. She is punctual, always on time and communicates very well. We will continue using her as our pet sitter. Thank you Jennifer.

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Tatyana A.
Drop-In Visits
5.0 out of 5 stars

Jackie was amazing with my Madison! I will definitely be using her again. So awesome to be able to leave my baby in trusting loving hands ❤️

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Wendy G.
Drop-In Visits
5.0 out of 5 stars

The best care for my four legged bestie! I repeatedly use Grace for her wonderful dog sitting service ❤️

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Victoria P.
Drop-In Visits
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Popular requests for dog sitting - Middletown

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Sitters in Middletown average 5
repeat dog sitting clients

FAQs for Drop-In Visits - Middletown

Frequently asked questions about Rover

The average cost for Dog Sitting in Middletown on Rover is $19.26 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 1,211 sitters on Rover offering Dog Sitting across Middletown. 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 Middletown 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 Middletown 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 Middletown 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 Middletown. On Rover:

  • 97% of sitters can help with special care needs
  • 98% 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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