Dog Sitting Chester

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

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Over 22
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Chester, 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.

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Sitter Profile Image: Elena K.
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Elena K.
from
$30
per visit
5.0 out of 5 stars
• 8 reviews
3 repeat clients
10 years of experience
Newburgh, NY, 12550

“I can’t say enough how happy I am with her service . My dog was well taken care of with gentle loving care. I am so happy . Thank you for the peace of mind”

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Cindy M.
Sitter Profile Image: Sarelle K.
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Sarelle K.
from
$35
per visit
4 years of experience
Pine Bush, NY, 12566

About: I have been an animal lover since day one!! I am an experienced hand-on Dog/Cat/Horse owner and Dog breeder. I love all types of breeds, sizes and personalities. I make it my priority to make sure your fur family member feels loved and safe on this new adventure. I’m an online college student so being home isn’t a problem for me. I enjoy spending time outside so tailoring your furry friends exercise schedule to mine will be a breeze. From first ruffs to mature ruffs i have experience taking care of fur baby’s of all ages! My experience includes puppy training to administering extra attention to old or sick fur baby’s making them most comfortable In a new setting. Every fur family member needs a unique style of care and I look forward to learning yours! I'm attentive, responsible, and genuinely invested in making sure your dog feels safe, loved, and comfortable at all times. My goal is to take care of your fur family as if it were my own. I’m excited to be apart of your fur family’s next adventure! I am an online college student so being at home is routine for me. I work at my own pace so caring for your fur family member comes first no matter what time it comes at. Whatever schedule your fur family member is used to is the least you can expect from me. Outside play time or walks - inside rest time or training, my goal is to make you and your fur family feel safe, happy, and comfortable. I live on several acres of property that is fenced in from the road, so playtime is not only fun but safe as well. I always keep visiting fur friends on a leash if outside just for extra safety. If your fur family member is used to a crate or three-count sheets you can be sure routine will be kept.

Sitter Profile Image: Samantha S.
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Samantha S.
from
$30
per visit
10 years of experience
Southside, Cornwall, NY, 12518

About: I have always had animals in my house ranging from reptiles to kittens. Currently I have three dogs and two cats. Growing up with animals has taught me how to care for a wide range of breeds and temperaments. Along with caring for my own animals I regularly sit for family and friends. I also have worked in a pet store where I learned how to care for puppies and kittens properly in a wide range of breeds. Between caring for their health needs to how to properly groom certain breeds. I am excited to help with your pets needs! Pet care fits into my daily and weekly routine well. I work a flexible job remotely that allows me to step away from my computer as needed allowing me to care for your animals when needed! I will care for your pets with all the love and attention to detail. I have worked with dogs that are high energy and need long walks to older animals that simply need someone to hang out with. I will pay close attention to your details about how to care for your animal and also what your animal needs at the time.

Sitter Profile Image: Catherine M.
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Catherine M.
from
$20
per visit
5.0 out of 5 stars
• 9 reviews
5 repeat clients
10 years of experience
Fishkill, NY, 12524

About: I am a lifelong dog owner. I have experience walking and training dogs. I love dogs and learning about all the different breeds. As a pet parent I understand about keeping pets on s the daily schedule I work from home and my schedule is flexible which allows me to take care of my dogs. The dogs are by my side most of the entire day I get down to the dogs level and try to learn about their individual personality and breed of the dog that they are. I am always learning about dog behaviors.

Sitter Profile Image: Madelyn M.
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Madelyn M.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
• 49 reviews
17 repeat clients
15 years of experience
Montague, NJ, 07827

“Madelyn was wonderful and took great care of my fur baby even when my driveway was covered in snow and also helped us out over Christmas! Our cat is a needy boy and usually complains a lot when we leave but he didn’t seem to mind this time. Would definitely recommend!”

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Laura Z.
Sitter Profile Image: Kenniqua B.
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Kenniqua B.
Star Sitter
from
$65
per visit
5.0 out of 5 stars
• 19 reviews
4 repeat clients
10 years of experience
Marlboro, NY, 12542

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 dogs 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.

Sitter Profile Image: Phoebe L.
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Phoebe L.
from
$30
per visit
1.0 out of 5 stars
• 2 reviews
5 years of experience
Newburgh, NY, 12550

About: I’ve had dogs all my life and currently have three dogs at my parents house that I care for regularely when my parents need me to and I love it. I’ll come with treats and if your dog has any dietary restrictiond please let me know :) I’m currently working for Arc Midhudson on thurs-Sun at the moment! Sometimes there is variation in that schedule but that it for the most part :) I have a medical condition that may make me have to re schedule appointments but hopefully we can work together on it !! I could teach your dogs some basic tricks like sit and I am a good leash handler. I carry around a fanny pack with my dog stuff in it so it’s hands free and accessible for me.

Sitter Profile Image: Phalisity G.
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Phalisity G.
from
$15
per visit
4.8 out of 5 stars
• 18 reviews
5 repeat clients
10 years of experience
Wappingers Falls, NY, 12590

About: I have raised many puppies in my 10 years of experience. I like to take my dog and other fluffs on long walks through different parks and hiking trails. We always start the day with a high energy run/play at the park to get as much exercise in as possible. Throughout the day we go on shorter more frequent walks to keep her using the potty and help stay active. Our nightly walk consists of a long walk around our neighborhood to get out any extra energy so we can have a great nights sleep! I like to reward with treats and I don't mind animals on the furniture. Currently, I am a stay-at-home mom which makes me able to care for fluffs all day long. I still like to get in my exercise and taking the fluffs with me help keep me busy. I have a 4 month old puppy of my own who has MANY toys and places to sleep. She is very outgoing and house trained. I have space to crate your fluff baby if you'd like - please bring your own crate. I can also do basic puppy training as well - sit, lay, stay, handshake etc. I will also provide pictures and videos throughout our stay!

Sitter Profile Image: Katherine O.
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Katherine O.
from
$25
per visit
5.0 out of 5 stars
• 2 reviews
1 repeat client
10 years of experience
Valley cottage, NY, 10988

About: I’ve always been around animals. I grew up with a cat and two dogs(shelties)! Have had a few on my own and fostered! They are so special to me! They are the soul of our home. I love taking care of other pups and giving all my love and care! I have taken care of a range of dogs and cats. I worked for a pet sitting company while I lived in Idaho. I’ve worked with big dogs, old dogs, puppies, dogs with physical disabilities, health issues and anxiety pups! I’m currently working from home with a very flexible schedule! I can’t stop by whenever and I am very active! If they need a walk or run that is no problem! I will give them so much love and cuddles! Walks if needed as well! I am very active and love playing fetch with doggies! I have expierence with old And young doggies. If they need medicine administered that is no problem!

Sitter Profile Image: Sidra R.
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Sidra R.
from
$50
per visit
5.0 out of 5 stars
• 3 reviews
5 years of experience
Pine Bush, NY, 12566

About: From overnight stays and walks to playtime and cuddles, family and friends have entrusted me with the care of their fur baby. Being able to work with cats and dogs on a daily basis as a veterinary assistant continues to help me accumulate various skills to work with animals of all temperaments and ages! I’m currently working part time so I’d have flexible time to spend with your precious pups whether during the week or during the weekend ! Pups are off if their routine is off so if you have a specific schedule or way of doing things I can assure you I will stick to the game plan.

Sitter Profile Image: Farva S.
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Farva S.
from
$30
per visit
4.9 out of 5 stars
• 121 reviews
80 repeat clients
17 years of experience
Pound Ridge, NY, 10576

“Farva was available last minute and really helped us out when we booked a last minute trip! She was very responsive, prompt and professional. We’d definitely use her again!”

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Amanda L.
Sitter Profile Image: Tracy & Steven C.
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Tracy & Steven C.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
• 125 reviews
20 repeat clients
45 years of experience
Verona, NJ, 07044

“Tracy and Steve were incredibly communicative throughout the entire stay, sent regular updates and videos of Dakota, and made me feel completely at ease while I was away. They were so kind, easy to talk to, and genuinely cared about her. They even left her treats and a thoughtful note, which was such a sweet surprise. I would absolutely trust them with Dakota again😊”

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Stacy W.
Sitter Profile Image: Dominick V.
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Dominick V.
from
$25
per visit
5.0 out of 5 stars
• 2 reviews
1 repeat client
12 years of experience
Rockaway Township, NJ, 07866

About: I’ve taken care of several different dog breeds since the age of 8. Mostly larger breeds ranging from a golden retriever to an Alaskan Malimute. My care ranges from basic walking , bathing, and grooming, down to medication management and insulin shots. Currently I’m looking for another part time job, but at the moment I’m eager to get started working with your pets full time. When I do secure employment it will just be part time in the mornings. With the utmost respect. Our pets are like our children and I would want someone to handle mine with care, compassion, and respect and I plan to do the same for you.

Sitter Profile Image: Sierra C.
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Sierra C.
Star Sitter
from
$30
per visit
4.9 out of 5 stars
• 50 reviews
17 repeat clients
10 years of experience
Englewood, NJ, 07631

About: Hi Im CeeCee (30). Leaving your baby, is already anxiety inducing, and frustrating as it is. And finding a trusted sitter just adds more to the mental load. With that being said, I make it my business to provide the most reassurance to You and your baby that there will be nothing but love and cuddles while you’re away. I have worked with animals since 2015 getting my start at Camp Bow Wow in Elmwood park and have worked at many prestigious hospitals in multiple states since. I love animals whether it’s cats/dogs or birds and reptiles. They are all so amazing to me. Grooming and distributing medication can be done at your request. I dont mind large dogs at all. Puppies are also welcome. I love to exercise, so your pup and I shall be doing some running around outside. Photography is my side hobby so please be prepared to be flooded with lots of pictures. All pups will go on 3-4 walks a day. More walk can be requested. Am walks: 6-7 am Afternoon walks: 12pm-1pm Pm walks:6pm-7pm Late late walks: 11pm-12am I treat all fur babies how I’d want my own to be treated. In case of emergency I live very close to multiple animal hospitals.

Sitter Profile Image: Maria L.
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Maria L.
from
$30
per visit
5.0 out of 5 stars
• 7 reviews
10 years of experience
Nyack, NY, 10960

About: Dog sitting has become the best full time job here! I have never been paid to dog walk/sit and only have purely out of love for all animals. I started volunteering for family friends and neighbors at a young age and will never say no to hanging out with a furry friend. No size or breed scare me - all are welcome (: Boarding - I am home everyday and have full availability to watch and care for pups. Yard is moderately sized and property is pretty private with our only 3 neighbors all across the street. I have many repeated clients outside of rover and we’re constantly rotating dogs so expect your pup to make furry friends during their stay! For walks - my schedule is extremely flexible at the moment, preferably mornings and late afternoons. Tuesday and Wednesday evenings are not ideal but can possibly work. Sunday mornings do not work. I have a mini goldendoodle living in my studio apartment. She is shy but warms up quickly to new pups. My apartment is the lower half of my dad’s house in a private wooded area on a hill overlooking the Hudson River. I am a free range sitter so pups are allowed on sofa and bed unless I’m given specific instructions which I happily will follow.

Sitter Profile Image: Bryan A.
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Bryan A.
from
$27
per visit
5.0 out of 5 stars
• 4 reviews
1 repeat client
2 years of experience
Lake Hopatcong, NJ, 07849

“Bryan was great with our dogs. He was punctual, attentive, and communicative. We will definitely rebook with him and strongly recommend.”

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Matthew D.
Sitter Profile Image: Patricia H.
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Patricia H.
from
$50
per visit
5.0 out of 5 stars
• 6 reviews
2 repeat clients
20 years of experience
Poughkeepsie, NY, 12601

About: I have been a pet lover & pet care advocate for as long as I can remember! I’ve been caring for dogs of all breeds, sizes, and personalities my entire life. I’ve taken care of kittens, pups, rescued cats, & cared for other pets like bunnies, fish, & hamsters. Over the years, friends, family, and neighbors have trusted me to walk, feed, and love their pets like my own which I do with a smile. Whether it’s an energetic puppy who needs to play & burn off some energy, or a sweet senior pup who needs extra patience and care, I adapt to their unique needs and personalities. I’m not just a sitter, i’m an emotional support human & a dependable companion for your pet while you’re away. I believe in consistent communication, lots of love, and making sure your pet feels safe, happy, and cared for. I love & care for them as if they were my own. I’m experienced with administering medications, sticking to routines, and keeping pets calm and comfortable in their own environment. Your comfort, peace of mind, & your pet’s happiness are my top priority! As someone who works from home and takes online classes, my schedule is super flexible; perfect for giving your pet the attention they deserve! I’m home throughout the day, which means your pet won’t be left alone for long stretches. Whether it’s a midday walk, playtime, or just some company while they nap, I can be there when they need it most. My routine allows me to be fully present and responsive to your pet’s needs. I can stick to their feeding and walking schedule, provide consistent companionship, and make sure they feel safe, loved, and entertained while you’re away. Being home all day also makes me a great fit for puppies, senior pets, or dogs who need a little extra TLC. When I care for pets in their own home, my goal is to keep their routine as familiar and stress-free as possible. I follow your pet’s routine closely & I make sure they’re comfortable in their space, following their usual schedule for walks, meals, playtime, and cuddles. Whether it’s sticking to their favorite walking route or knowing exactly how they like their food prepared, I pay close attention to every detail you share. I know how much the little details matter! Being in their own environment helps your pet feel more relaxed, and I’m there to make sure they feel loved every step of the way. I’m experienced in administering a variety of medications, including flea and tick ointments, oral chewy meds, and pills; whether they’re hidden in a treat or given directly. I stay calm and patient to make the process as stress-free as possible. I’m comfortable managing multiple pets and giving each one the attention and care they need. I treat your home with the same respect and care I give to your pet: clean, secure, and exactly how you left it. I provide regular updates with messages & photos so you can feel confident your pet is safe, happy, and in good hands & know everything is going smoothly while you’re away.

Sitter Profile Image: Vincent T.
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Vincent T.
from
$35
per visit
4.8 out of 5 stars
• 38 reviews
8 repeat clients
13 years of experience
Cedar Grove, NJ, 07009

“Vincent was a huge help while we were out of state for a few nights. We had a bad experience at a kennel so we turned to Rover. Vincent was trustworthy , responsive, friendly, and was able to handle a large giant schnauzer puppy with a lot of energy. We’ll be working with him again !”

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Niall
Sitter Profile Image: Shinyoung P.
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Shinyoung P.
from
$30
per visit
5.0 out of 5 stars
• 6 reviews
4 repeat clients
20 years of experience
Morningside Heights, New York, NY, 10027

About: What sets me apart as a sitter is my deep love for animals combined with a calm, reliable, and intuitive approach to care. I specialize in both energetic puppies and gentle senior dogs, understanding the unique needs of each stage. Whether it’s crate training, potty schedules, or administering medications, I provide attentive, tailored support. I treat every dog like family—always ensuring they feel safe, loved, and understood. With a background in wellness and a natural sense of routine, I’m great at maintaining structure while giving plenty of affection and play. Pet care is a natural and joyful part of my daily routine. I build my schedule around the needs of the pets in my care—whether that means early morning walks, midday playtime, or relaxed evening check-ins. I work remotely and have a flexible lifestyle, which allows me to give pets consistent attention, structure, and affection throughout the day. Your pup’s well-being becomes my top priority, and I love creating a rhythm that keeps them happy, healthy, and at ease. Safety, trust, and comfort are my top prioritie- whether I’m caring for your pet in your home or mine. I always take time to understand your dog’s routine, preferences, and personality, so I can create a stress-free, familiar environment. In your home, I maintain your pet’s usual schedule and surroundings to help them feel secure. In my home, pets are treated like family with a clean, calm space that’s both cozy and supervised. I follow any feeding, medication, and exercise instructions exactly and keep you updated with messages and photos, so you feel confident and connected while you’re away.

Sitter Profile Image: Jorge P.
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Jorge P.
from
$50
per visit
4.9 out of 5 stars
• 90 reviews
34 repeat clients
10 years of experience
Washington Heights, New york, NY, 10032

“Jorge was an excellent pet sitter for my resident cat and my foster cat. I didn’t worry once about their well-being while on vacation. He was on-time/early for every appointment and sent me updates regularly when need be. I will definitely be calling on Jorge again in the future for pet sitting, and would highly recommend him to anyone who is looking for a reliable and caring sitter for their pet(s).”

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Renee R.
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The median cost per visit for dog sitting in Chester is $25

Dog parents share their Rover experiences - Chester

1 / 1
5.0 out of 5 stars

Brittany was fantastic with my babies! Thorough and detailed with my instructions my babies were happy and comfortable. Highly recommend!

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L K.
Drop-In Visits
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How to book dog sitting

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Popular requests for dog sitting - Chester

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Sitters in Chester average 5
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FAQs for Dog Sitting - Chester

Frequently asked questions about Rover

The average cost of Dog Sitting in Chester on Rover is $33 per visit as of October 2026. Most bookings cost between $24 and $52 per visit. sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 2,417 sitters on Rover offering Dog Sitting across Chester. Enter your ZIP code to see which available sitters are closest to your home.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

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 Chester 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 .

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 , which provides up to 25,000 in eligible veterinary care reimbursement.

A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .

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 Chester 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 Chester. On Rover:

  • 93% of sitters can help with special care needs
  • 96% 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 , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.

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