Dog Sitting Chesterland

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

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Over 17
pet parents in Chesterland have booked dog sitting

Chesterland, 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: Takia B.
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Takia B.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 38 reviews
14 repeat clients
4 years of experience
Lee Miles, Cleveland, OH, 44128

“Takia has been absolutely amazing! She checked in on my dog for 5 days and always sent multiple photos daily with paragraph updates. My dog needed oral meds daily and she was able to give with no issue at all! She even added cuddles with my pup as a cherry on top! Thank you Takia for the kind loving care towards my best friend. We will definitely be returning customers 🐶❤️”

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Courtney R.
Sitter Profile Image: Brooke T.
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Brooke T.
from
$30
per visit
5.0 out of 5 stars
• 3 reviews
2 repeat clients
6 years of experience
Chardon, OH, 44024

About: I’ve had quite a lot of animal experience! From working in a humane society, grooming, certification in pet nutrition, to owning my own in-home pet care business (Happy Feet Pet Care). I love what I do and can’t wait to meet you and your furry ones🐶🐱 I work full time as a in-home pet care taker. I recently opened up my own business and am ready to take any action I can get! Great supervision on your pets, i’m certified in pet nutrition and have been trained on body language as well. I have a genuine passion for all animals, I treat them as my own! I also love to apply training into the pet care that I do.

Sitter Profile Image: Omega F.
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Omega F.
Star Sitter
from
$32
per visit
5.0 out of 5 stars
• 147 reviews
52 repeat clients
16 years of experience
North Collinwood, Cleveland, OH, 44119

“Omega has been terrific, giving 5 meds per day to my old kitty. She checked in via the app each of the three times a day thst she visited, & I appreciated the photos, taken in various locations. My stand-offish kitty even rubbed up against her after a couple of days! Thanks so much, Omega, I will def request you again!”

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Polly M.
Sitter Profile Image: Erin L.
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Erin L.
from
$25
per visit
15 years of experience
Willoughby, OH, 44094

About: I’ve always loved animals and enjoy giving pets the attention, care, and companionship they deserve. I’m comfortable caring for pets in their home, taking dogs on walks, and stopping by throughout the day for meals, potty breaks, playtime, and plenty of love. I understand that every pet has their own personality, routine, and needs, and I’m happy to follow your instructions to keep them comfortable and on schedule. Whether your pet needs an energetic walk, some company while you’re away, or a little extra attention at home, I’ll treat them like they’re my own. I’m reliable, communicative, and will keep you updated with photos and messages so you can feel confident your pet is happy and well cared for while you’re away. **For first time visits please book at least 3 days in advance so we can make sure we can schedule a meet & greet** I work remotely, which gives me a flexible schedule and allows me to be available for walks, drop-ins, and house sitting throughout the day. I’m able to work my pet-care schedule around my meetings and work responsibilities, and I’m happy to coordinate with your pet’s routine and needs. I’m especially flexible for daytime walks and drop-ins, as well as house sitting when needed. I’ll always make sure I have plenty of time to give your pet the attention, exercise, and companionship they need while still keeping up with my work commitments. I treat every pet like they’re my own and make sure they feel safe, comfortable, and cared for in their usual routine. I’m happy to follow your instructions for feeding, walks, medication, playtime, and any other special needs or preferences. Since I work remotely, I’m able to be flexible and provide plenty of companionship throughout the day while working around my meeting schedule. For walks and drop-ins, I’ll make sure your pet gets exercise, attention, potty breaks, and plenty of love. For house sitting, I’ll keep their routine as consistent as possible and make sure they’re never without the care and companionship they’re used to. I’ll also keep you updated with photos and messages so you can relax knowing your pet is happy and well cared for.

Sitter Profile Image: Kaitlyn H.
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Kaitlyn H.
from
$25
per visit
5.0 out of 5 stars
• 10 reviews
3 repeat clients
4 years of experience
Painesville, OH, 44077

About: I have taken care of dogs since I was in High School. I have had a number of dogs and cats. I had a 2 year old golden doodle named Willow who has since passed. I understand the idea of how important our pets are to us and I always make sure when I am watching someone else's pet I am treating them as my own. I am a travel RN who is home for the holidays, possibly longer! I am taking time off and would love to care for your pets in my free time! I have 3 adorable cats and 1 loving golden retriever! I live in a house with an acre backyard where all the animals run and play! There is no fence, let me know if you would feel more comfortable with me using a leash for outside time(:

Sitter Profile Image: Marti G.
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Marti G.
from
$22
per visit
5.0 out of 5 stars
• 11 reviews
3 repeat clients
11 years of experience
Cleveland Heights, OH, 44118

“Marti took great care of my two kitties! I would recommend her to anyone looking for a drop in sitter. She was very communicative and helpful. I came home to two happy cat brothers😻”

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Rosemary H.
Sitter Profile Image: Madaline R.
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Madaline R.
from
$25
per visit
5.0 out of 5 stars
• 5 reviews
15 years of experience
Mentor, OH, 44060

About: My passion for caring for animals began in childhood while growing up on a farm. From a young age, I helped clean stalls, collect fresh chicken eggs each morning, and care for a variety of animals. I was always the kid begging my parents for more pets, and animals quickly became my greatest source of comfort through a tough childhood. I have over 10 years of hands-on experience working on a horse farm, where I learned the value of consistency, safety, and attentive care. In addition, I’ve fostered bottle-baby kittens, assisted my mom in breeding golden retrievers, and helped raise her litters many times. My love for animals has no boundaries — I’ve worked with everything from farm animals to dogs, cats, and even jumping spiders, which I currently breed. I have two dogs of my own — Meme, who is 6, and Pia, who is 3 — and they are my whole heart. They have a daily routine I take seriously: outside time at 6:00 a.m., treats before I head to work, a midday potty break, and an evening 30-minute walk at 5:30 p.m. On weekends, we enjoy adventures at the park or exploring new places. I understand how important structure and routine are for pets, and I treat every animal in my care as if they were my own. Over the years, I’ve provided a wide range of pet care — from weekend stays to week-long vacations — both in my home and in others’. Whether it’s an active pup needing exercise, a senior dog requiring gentle attention, or a young animal that needs extra patience, I’m flexible, attentive, and committed to giving each pet the love, safety, and care they deserve. My pups have an entire routine each day. In the morning they go outside at 6:00 am. I do have a fenced in back yard, so I leave my sliding glass door open so they may come in and out. The get treats in the morning before I go to work. I do return home for lunch to let them out to potty. I return home around 5:30 each day and we go for a 30 minute walk. They get their bedtime treat and we start again the next day. On weekends I do like to take them to the park or on adventures. My pups would love some friends, and sleep overs. I know how important my dogs routine and/or schedules are and I would take your pup’s routine just as seriously. The amount of care I offer for pets on a regular basis always fluctuates. I have had pups for a week long vacation, and I have also had just weekend stays. Various weekends I do stay at others homes and care for their pets. I’m very flexible.

Sitter Profile Image: Ashley M.
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Ashley M.
from
$35
per visit
4.6 out of 5 stars
• 16 reviews
2 repeat clients
6 years of experience
Kirtland, OH, 44092

“This was my first time having a sitter, and therefore my first time leaving my cat for a trip that was longer than a few days. Even though I was nervous, Ashley did a great job by ensuring me she was capable and excited to take care of my cat. While my cat doesn’t have any specific medical concerns, I do know she can be a bit finicky and I was worried about her not eating while I was away. Not only did my cat love Ashley and continued eating, I got updates even though I wasn’t able to view them for a while, due to international travel that I could look back at and know that she was well taken care of. My home and my cat were safe while I was on my vacation and I could be stress-free. If I ever need to travel again, I will definitely be booking with her in the future.”

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Nicole S.
Sitter Profile Image: Em K.
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Em K.
from
$30
per visit
5.0 out of 5 stars
• 6 reviews
1 repeat client
15 years of experience
Willoughby, OH, 44094

About: I love the clients I get to work with as a pet sitter. I love providing stress free and reliable pet care for people when they need the help. It's a big deal to let someone into your home and trust them with the care of your pets. I understand the responsibility and don't take it lightly. I am experienced with puppies and dogs, cats and farm animals, special needs, reactive and senior dogs. I treat others' pets as if they were my own. It brings me a lot of joy to make your pet feel loved, happy and safe. I'm comfortable crating, walking, giving medicine and other special needs. There's nothing I won't do for your pet - its a very important member of your family! I can provide any additional references upon request! Pet sitting fits into my routine perfectly because I work remotely, so I have the flexibility to be with your animal/s as much or as little as you prefer! I care for my clients pets based on their requests, preferences and routines. I am comfortable walking, crating, giving commands, and following each person's instructions for how they want their animals to be cared for.

Sitter Profile Image: Ines N.
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Ines N.
from
$30
per visit
4 years of experience
Solon, OH, 44139

About: Hello! I have helped friends and family take care of their pets for years. I would love to spread the joy with you as well. Currently, I am waiting for the school year to begin so I have the possibility to do multiple drop ins. My hours range from 5am to 12am. I live in a gated community with a large backyard. I believe it’s the perfect amount of space for running, playing fetch, or just lounging.

Sitter Profile Image: Rebecca G.
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Rebecca G.
from
$25
per visit
5.0 out of 5 stars
• 2 reviews
1 repeat client
30 years of experience
Streetsboro, OH, 44211

“Rebecca took great care of Wilkie she took pictures, an communicated well. I would would rebook”

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Felicia H.
Sitter Profile Image: Cassie W.
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Cassie W.
from
$40
per visit
5.0 out of 5 stars
• 8 reviews
1 repeat client
15 years of experience
Mentor, OH, 44060

About: There has never been segment of time where I did not have a pet— dogs, cats, ferrets, hamsters, fish, a baby squirrel. I started pet-sitting for neighbors & family friends during high school and continued to accept requests through word-of-mouth. I have experience with puppies, seniors, special needs, and pets with less-than-friendly personalities. All pets are welcome with me. I work full-time in healthcare, the standard M-F, 9-5. Your pet’s morning & evening routine will be carried out thoroughly with plenty of outdoor time. Weekends will be invested with your pet. If they can tolerate a hike, then we’ll definitely be taking a field trip. Your pet's comfort and entertainment is my responsibility. I will follow your pet's schedule & routine and support your training efforts to the best of my ability. The ultimate goal is for your pet to not even know that you left.

Sitter Profile Image: Tracee Z.
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Tracee Z.
from
$30
per visit
5.0 out of 5 stars
• 5 reviews
40 years of experience
Concord, OH, 44077

About: I have had dogs my entire life. Currently, I have 2 dogs and a bunny. I adore animals and enjoy quality time with them. They are family and deserve the best… I’ll treat your best friends like my own! Experience taking care of dogs of all sizes and ages. I currently have a very flexible schedule. Pet sitting and walking is something I do because I enjoy it. i am available most times of day, 7 days a week. I am comfortable with enclosed fencing, invisible fences, leashes and tie outs. Whatever your pet is used to will work for me. I am responsible, dependable and very careful to make sure your home and pets are safe.

Sitter Profile Image: Maria D.
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Maria D.
from
$35
per visit
5.0 out of 5 stars
• 7 reviews
3 repeat clients
7 years of experience
Solon, OH, 44139

About: Hi! I’m Maria, and caring for animals isn’t just something I do, it’s something I’ve dedicated years of my life to. I have over 10 years of hands on experience working with dogs of all ages, sizes, breeds, and personalities. From energetic puppies to senior dogs who need a slower pace, I understand that every pet deserves care that’s tailored specifically to them. My partner and I work together as a team, which means your pets receive twice the attention, care, and reliability. Having two experienced animal lovers allows us to be flexible with scheduling and provide consistent, dependable care for your pets, whether you’re away for the day or an extended vacation. I offer: • Dog Walking • Drop-In Visits • House Sitting • Overnight Boarding • Puppy Care • Senior Dog Care • Medication Administration (if needed) • Lots of playtime, cuddles, enrichment, and exercise! I’ve cared for everything from tiny toy breeds to giant breeds, including dogs with anxiety, high energy, special routines, and unique personalities. I also have experience with cats and other household pets, so if your family includes more than just dogs, they’re in great hands too. When your pet stays with us or we care for them in your home, they’re treated like family. We stick to their normal routine as closely as possible because we know consistency helps pets feel safe and comfortable. Whether that means long walks, endless games of fetch, quiet cuddle time, or simply keeping them company, we adjust our care to what makes your pet happiest. As pet owners ourselves, we understand how difficult it can be to trust someone with a member of your family. That’s why communication is one of our top priorities. You’ll receive regular updates, photos, and messages so you can enjoy your time away knowing your pet is happy, loved, and well cared for. Our goal isn’t just to watch your pet. We want to become someone both you and your furry family member can trust for years to come. We’d love the opportunity to meet you and provide the same love, patience, and attention we give our own pets every single day. We can’t wait to meet your best friend! 🐾 One of us works full time, however the other stays at home and focuses on animals and etc. We’re always able to be flexible and accommodate everyone’s needs We always make sure to meet prior to bookings and if needed or wanted to I do like to send pictures and videos of your fur babies while in my care. I know everyone misses their little babies.

Sitter Profile Image: Melissa D.
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Melissa D.
from
$20
per visit
5.0 out of 5 stars
• 5 reviews
3 repeat clients
15 years of experience
Perry, OH, 44081

About: I've been around animals since I was very young and love all of them. They are part of my family and will be treated as such while they're with me. I enjoy going on walks and keeping pets happy and entertained. I believe it's very important to know your fur babies will be in great hands when boarding with me. My beloved dog Mario is no longer with me; he lived for 13 wonderful years and was the best dog anyone could ask for. I haven't been able to get another one since then. Watching and caring for other pets makes me happy and brings me joy. I currently work from home so my schedule is very flexible throughout the week. Working from Home is a blessing and has given me the flexibility to care for others pets. I do not have a fenced yard, but I live in a development that gives me plenty of opportunities to go for walks. As long as they come with a leash we will be walking.

Sitter Profile Image: Keri D.
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Keri D.
from
$30
per visit
5.0 out of 5 stars
• 8 reviews
3 repeat clients
15 years of experience
Mentor, OH, 44060

“She truly went above and beyond, I am so impressed and happy she could visit our pets while we were gone.”

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Casey F.
Sitter Profile Image: Raegan B.
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Raegan B.
from
$20
per visit
5.0 out of 5 stars
• 75 reviews
33 repeat clients
20 years of experience
Parma, OH, 44134

“Love having Reagan come for my cat. He seems to really enjoy her visits and I get the best pic updates 🥰. Also so easy to communicate with, thanks for staying with my Charlie again!”

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Melissa S.
Sitter Profile Image: Tamara R.
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Tamara R.
from
$30
per visit
45 years of experience
Brecksville, OH, 44141

About: Dogs, cats & birds have been my life’s passion for over 45 years. I’ve rescued, rehabilitated, and rehomed more than 100 dogs, cats, kittens, puppies & birds—providing medical care, stability, and love every step of the way. I’ve trained everything from energetic puppies to adult dogs, birds, and even cats, always tailoring my approach to each animal’s personality. I’m also skilled in giving medications, shots, and IV fluids, and I’m experienced with special-needs pets—those with seizures, hearing loss, food sensitivities, or emotional trauma. I’ve never turned away an animal in need, no matter how inconvenient or challenging the situation. My commitment runs deep—every rescue has taught me something, and each one holds a special place in my heart. As a lifelong pet parent and rescuer, I understand the trust it takes to leave your pets in someone else’s care. I follow each owner’s routines and training guidelines closely to ensure every pet feels safe, loved, and comfortable while you’re away. I’d be honored to give your furry (or feathered!) family member the same care and devotion I give my own! Available most days with notice. I currently provide heath care for my father & I have my own pack of 3 dogs & 2 cats. I will pay close attention to the parents requests, schedule &/or medical needs. I have nothing but great respect for the clients rules& home. I promise you to provide an experience we’re all the clients needs are met!

Sitter Profile Image: Ariel E.
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Ariel E.
from
$25
per visit
4 years of experience
Bristolville, OH, 44402

About: Hi! My name is Ariel, and I’ve loved animals for as long as I can remember. As a dog owner myself, I understand that pets are family, and I know how important it is to leave them with someone you can trust. My goal is to make every pet feel safe, loved, and comfortable while you’re away. I have experience caring for dogs of different sizes, personalities, and energy levels. Whether your pup loves long walks, playing fetch, cuddling on the couch, or simply sticking to their normal routine, I’m happy to provide personalized care based on their needs. I’m currently in nursing school, which has strengthened my attention to detail, patience, and responsibility. I’ll always treat your pet as if they were my own, keeping you updated with plenty of photos and messages so you can have peace of mind while you’re away. I can’t wait to meet you and your furry best friend! As i’m currently in nursing school, my schedule is always fluctuating, but I make it a priority to provide dependable, attentive care for every pet I look after. I keep my Rover calendar updated so you always know my availability. Whether your dog needs a walk, a drop-in visit, or extra playtime and cuddles, I’ll make sure they receive the love, attention, and care they deserve. I also believe communication is key, so you can expect regular updates and plenty of photos, giving you peace of mind while you’re away. Your pet’s safety and comfort are my top priorities! I will take the time to learn each dog’s routine, personality, and any special needs before every visit. I will be sure to provide fresh water, regular potty breaks, exercise, playtime, and lots of affection while ensuring doors, leashes, and gates are always secure. I’ll treat your home with respect and care for your pet as if they were my own. You can also expect regular updates and photos so you always know how your furry family member is doing.

Sitter Profile Image: Tabbi W.
Verified Background Check
Tabbi W.
from
$30
per visit
5.0 out of 5 stars
• 24 reviews
8 repeat clients
18 years of experience
Hudson, OH, 44236

“Tabbi was awesome with the pet kids! She had a challenge and she conquered it! The dogs were so happy when she stopped in 3 times each day to walk water and feed them. She sent us pictures and a report card for every visit. We will definitely give Tabbi a call the next time we need a sitter for Sadie and Ranger!”

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Teresa H.
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The median cost per visit for dog sitting in Chesterland is $20

Dog parents share their Rover experiences - Chesterland

1 / 1
5.0 out of 5 stars

Lindsey is amazing with our shy little girl. Very patient and sends us updates so we know everything is good!

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Tracy C.
Drop-In Visits
5.0 out of 5 stars

Highly recommend Hannah who took great care of our dog. She showed up on time and sent photos as well. Look forward to using her again soon!

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Amy D.
Drop-In Visits
5.0 out of 5 stars

She stopped by for a check in on my dogs while we were out of town. My dogs absolutely loved her, she was very responsive on needs that needed to happen for my dogs and even sent pictures of them! Would definitely recommend her to anyone needing their dogs taken care of!

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Dawson C.
Drop-In Visits
5.0 out of 5 stars

Great communication before, during, and at the conclusion of her visit. Will definitely reach out again for further needs.

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Brandie A.
Drop-In Visits
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How to book dog sitting

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Popular requests for dog sitting - Chesterland

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Sitters in Chesterland average 6
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FAQs for Dog Sitting - Chesterland

Frequently asked questions about Rover

The average cost of Dog Sitting in Chesterland is $16 per visit as of November 2026. Most bookings cost between $11 and $34 per visit. On Rover, 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 November 2026, there are 2,129 sitters on Rover offering Dog Sitting across Chesterland. 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 Chesterland 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 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 Meet & Greet.

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 Chesterland 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 Chesterland. On Rover:

  • 89% of sitters can help with special care needs
  • 94% can help with giving oral medications or injections
  • 95% 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 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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