House Sitting Choptank Overlook

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

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Sitter Profile Image: Pamela A.
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Pamela A.
from
$65
per night
5.0 out of 5 stars
• 40 reviews
12 repeat clients
31 years of experience
Hillsboro, MD, 21641

“She was fantastic! Came to the meet-and-greet well prepared, was super communicative throughout the booking, and made everything stress-free. My dog was well cared for, and I felt completely at ease. 10/10 recommend and would absolutely book again!”

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Caleb M.
Sitter Profile Image: Kelly C.
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Kelly C.
from
$65
per night
4.9 out of 5 stars
• 13 reviews
3 repeat clients
10 years of experience
Preston, MD, 21655

“This was a last minute arrangement on our part, so we were a bit nervous, as we did not get a chance to meet Kelly before allowing her in our house to care for our dogs. She was great! She let us know as soon as she arrived, sent us pics and videos several times in just two days. The dogs were very happy and so were we. We would certainly invite her back in the future.”

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Stephen W.
Sitter Profile Image: Danielle S.
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Danielle S.
from
$45
per night
5.0 out of 5 stars
• 7 reviews
3 repeat clients
15 years of experience
Magnolia, DE, 19962

About: I have taken care of a variety of dogs, I walk them, feed them and bath them if needed. I have taken care of dogs from puppies to senior care and providing medicine. I currently work full time with a variety on my schedule and very flexible, I love spending time with companions. Im passionate about giving the animals undivided attention. In my home I have a chain and an electric fence so my dog is provided the whole yard. I also have a crate if needed. I prefer to do in clients home to reduce the stress on the animal.

Sitter Profile Image: Katherine C.
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Katherine C.
from
$27
per night
5.0 out of 5 stars
• 19 reviews
4 repeat clients
13 years of experience
Easton, MD, 21601

About: I’ve worked with animals since I was 16. I love all breeds and species. I currently work on a thoroughbred horse farm. I love all pets like they are my own. I am comfortable administering medications, injections, and with aggressive/scared pets. I am willing to travel to the pets home. I will take the pet on leashed walks and give them lots of love. I’ll be able to communicate with clients and work with their needs. I’m very accommodating and just want the best for the client and pet. I would care for your pet like it’s my own. I take my own dogs on multiple walks throughout the day. At night I make sure they have plenty of water and I make sure they eat their dinner at the same time everyday because dogs like consistency. When I put the dogs to bed I sleep with them or if they sleep better in their crate I make sure their dogs bed is clean and their blankets are fluffed up. I like to keep a dogs routine the same so I will ask the owner their normal routines and I’ll do the same.

Sitter Profile Image: Imani W.
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Imani W.
from
$31
per night
5.0 out of 5 stars
• 2 reviews
1 repeat client
20 years of experience
Easton, MD, 21601

“Imani did a great job! Our three dogs were happy and well cared for. She was very nice and sweet.”

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Margaret P.
Sitter Profile Image: Lydia S.
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Lydia S.
from
$55
per night
4.8 out of 5 stars
• 5 reviews
2 repeat clients
7 years of experience
Felton, DE, 19943

“This was our first time using Rover and Lydia made it such an easy and wonderful experience for us. We came home to a clean house and very happy pups! We have issued other pet sitting services before but we’ll for sure be using Rover, and hopefully, Lydia again.”

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Ashley W.
Sitter Profile Image: Summer B.
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Summer B.
from
$125
per night
5.0 out of 5 stars
• 2 reviews
20 years of experience
Wye Mills, MD, 21679

About: ✨ Schedule & Availability I currently maintain a full-time position but please do not hesitate to reach out and we can talk about options to accommodate your pets needs. ‼️Currently can only guarantee afternoon services on Monday and Tuesday. ✅House sitting includes Morning and Evening services with overnight care. ✨My Experience I have experience caring for both dogs and cats with a wide range of personalities, energy levels, and care needs. In addition to caring for my own pets over the years, I have multiple years of providing care to clients, and volunteered with animal rescue and shelter organizations. I currently work full-time, but I still maintain availability outside of my work schedule for pet care, drop-ins, walks, feedings, and quality time with your pets. I’m reliable with routines and make sure pets receive the attention, consistency, and care they need while their owners are away. I understand how important trust is when someone is caring for your pets and entering your home. I treat every animal with patience, respect, and attention to their individual comfort level and routine. I’m experienced with shy pets, senior animals, anxious pets, and pets that may need a calmer approach or extra time to adjust. I always prioritize safety, clean environments, secure doors/leashes, and careful attention to instructions so owners can feel confident their pets are being cared for like family.

Sitter Profile Image: Krista K.
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Krista K.
from
$111
per night
5.0 out of 5 stars
• 15 reviews
4 repeat clients
10 years of experience
Camden, DE, 19934

“Krista did an amazing job! She was very friendly and our dog Molly did great with her. Krista was very attentive to Molly and was very respectful of our home. She kept us updated and sent pictures! We will definitely be having Krista watch our fur baby again! Thank you Krista ❤️”

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Jean D.
Sitter Profile Image: Chelsea-Rose L.
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Chelsea-Rose L.
from
$50
per night
5.0 out of 5 stars
• 43 reviews
15 repeat clients
10 years of experience
Lewes, DE, 19958

“We are so pleased with the experience we had with Chelsea. She was great about keeping us informed about how our pups were doing. She texted us and sent us pictures every day while we were out of town. We would definitely recommend Chelsea for anyone looking for someone to care for their pups.”

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Tim M.
Sitter Profile Image: Stephanie R.
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Stephanie R.
from
$75
per night
5.0 out of 5 stars
• 7 reviews
2 repeat clients
10 years of experience
Oxford, MD, 21654

“Stephanie took great care of my dog Sammy. I am thankful I found her. She was wonderful.”

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Mary O.
Sitter Profile Image: Aliciya M.
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Aliciya M.
from
$70
per night
1 repeat client
15 years of experience
Queenstown, MD, 21658

About: I’ve lived with dogs and cats my entire life and have over 15 years of hands-on experience caring for pets. Growing up, my mom had five dogs—some of which had puppies—and I helped raise and care for them. I’ve also cared for cats in multi-pet households, including feeding, litter box maintenance, and creating calm, safe environments for shy or senior cats. Neighbors, friends, and family have trusted me for years to walk, feed, bathe, and care for their pets while they’re away. I now have a black Yorkie of my own, and I treat every animal I care for like part of the family—whether they bark or purr! I currently work part time- and have lots of free time! I will send out a daily schedule of what I’ll be doing with the pets! I will take your dog out on walks on our neighborhood trail outside! I also have a few ring cameras, and will send a lot of pictures/videos throughout the day.

Sitter Profile Image: Kayla J.
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Kayla J.
from
$90
per night
5.0 out of 5 stars
• 7 reviews
2 repeat clients
10 years of experience
Milford, DE, 19963

“She was great and my dogs loved her!”

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Cathleen T.
Sitter Profile Image: Steven H.
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Steven H.
from
$75
per night
3 years of experience
Stevensville, MD, 21666

About: I have hands-on experience caring for my own dogs, Koda and Eddie. Koda is a Cane Corso puppy, which has helped me learn the importance of patience, consistency, positive reinforcement, and proper exercise. I make sure my pups receive plenty of love, attention, playtime, and daily care while keeping their safety and comfort a priority. I understand that every dog has a unique personality and needs, and I would treat every pet in my care like family! 🐶❤️ Pet care is something I enjoy and make time for in my daily schedule. I strive to be flexible, dependable, and attentive to each pet’s needs, ensuring they receive plenty of exercise, attention, and care. I communicate with pet parents to coordinate schedules and make sure every pup gets the time, love, and attention they deserve! 🐾 I prioritize safety, patience, and trust when caring for every pet. I make sure each animal feels comfortable, loved, and secure while following the owner’s instructions and respecting each pet’s unique needs. I believe in keeping open communication with pet parents, providing regular updates, and creating a safe, welcoming environment where both pets and their owners can feel confident and at ease. My goal is to treat every pet like family! 🐾❤️

Sitter Profile Image: Ann B.
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Ann B.
from
$50
per night
10 years of experience
Middletown, DE, 19709

About: I’ve been a devoted dog owner for 10 years, and I’m passionate about both dogs and staying active. As a schoolteacher, I’m excited to continue doing what I love while earning extra income to help pay off my student loans and purchase supplies for my classroom. I can walk dogs Monday through Friday after 3:30 pm. If you’re running late and need someone to help out in a pinch, I'm happy to assist. I’m available on Saturday and Sunday to walk your furry friend three times a day, or more if needed. Our dog is incredibly spoiled and loved. Whenever I come home, she brings me her ball, and we play fetch before anything else. She is groomed monthly, walked several times daily, and receives constant attention. When we have salmon, we cook her a plain fillet, which she loves.

Sitter Profile Image: Kara S.
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Kara S.
from
$85
per night
5 years of experience
Preston, MD, 21655

About: I’ve taken care of animals all my life. I’ve always had dogs growing up and i’ve even grown up on a farm taking care of life stock. I am currently moving back home from South Carolina. I was born and raised on the Eastern Shore so when I move back home I will have a pretty flexible open schedule. I can easily crate your dog if need be but I have a huge house with a huge back yard for them to run freely in.

Sitter Profile Image: Terry C.
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Terry C.
Star Sitter
from
$75
per night
5.0 out of 5 stars
• 80 reviews
26 repeat clients
15 years of experience
New Castle, DE, 19720

“Terry is absolutely amazing!! I can’t say enough good things about her and how she went above and beyond in taking care of our two dogs while we were out of town. She loved and cared for them like they were her own, sending us updates and videos each day. We had an amazing vacation and was able to not worry a bit about how the dogs were adjusting - they were so happy and got so much attention with Terry!! She will be the first person we call whenever we need a sitter! Thank you Terry!!”

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Carrie H.
Sitter Profile Image: Brianne S.
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Brianne S.
from
$56
per night
4.0 out of 5 stars
• 4 reviews
1 repeat client
15 years of experience
Chester, MD, 21619

About: Before joining Rover I mainly provided my services through word of mouth. I have experience with providing basic medical care for dogs and cats, and training experience including potty training and easing separation anxiety. I have vast experience and knowledge on various breeds and their specific needs, and really just love being able to have the time and availability to be able to provide these services. They say a dog is a man’s best friend, but in my case, a dog has always been a woman’s best friend! I offer dog sitting, walking, training and boarding at my home as well. I am brand new to the app but I do have plenty of references and want to make all owners feel just as comfortable as I want to ensure their pets will feel with me! I currently work a part-time job from my home, so I have a flexible schedule and able to meet any needs your pet has. I am available everyday, all hours mainly, and can accommodate you and your pets schedule! In my home all pets are welcome. I have plenty of walking trails and a back yard for pets that stay at my home. I typically will customize the walks, food, bathing etc depending on the needs of the pet and what works best for them and the owner.

Sitter Profile Image: Chelsi M.
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Chelsi M.
from
$90
per night
5.0 out of 5 stars
• 9 reviews
3 repeat clients
5 years of experience
Bear, DE, 19701

About: I am here to take of your dog and to provide them the love they long when it’s vacation time for owners (or anytime you need to yourself). Provide exercise for dogs (usually in half-hour or one-hour increments). Pick up and dispose of dog droppings during walks. Check dogs' food and water supply to make sure basic needs are met after walks. I am very patient and show a lot of compassion towards dog. I just want them to feel at home away from home! I am also a very active person, so your dog will be able to have all of their fun they usually have or more when they are with me! I hope to walk your dog soon! Prices are non negotiable I am working from home currently. This will allow me to give your first baby all of the attention they desire. Please ask me any questions on any accommodations that we may be able to work out. I don’t have any pets of my own so if your fur baby isn’t fond of other pets they can feel secure being over my home. My I am close with my neighbors who do have friendly pets as well, so if your pet loves company, they can be easily accommodated. We also have a dog park walking distance from the complex

Sitter Profile Image: Alexis, Tammy & Jamie A.
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Alexis, Tammy & Jamie A.
Star Sitter
from
$110
per night
5.0 out of 5 stars
• 599 reviews
204 repeat clients
15 years of experience
Millersville, MD, 21108

About: 👋 Meet Your Caregivers: ❤️ Alexis I’ve had a big heart for dogs all my life—starting with my very first dog, Spencer, a Yorkie who lived to be 18.5 years old despite being medically challenged! Caring for him throughout his long life inspired me to pursue a career in the veterinary field. I am currently a remote student studying to become a Veterinary Technologist. Because I complete my coursework online from home, I have an extremely flexible schedule and spend the vast majority of my time dedicated to caring for pets. Whether going on neighborhood walks, playing fetch, or simply relaxing together, I am committed to keeping your fur-baby safe, happy, and loved. 📋 What We Need to Know Before the Stay To help us provide the absolute best individualized care, please share: Any preexisting medical conditions, medication schedules, or dietary needs. Behavioral quirks, triggers, or leash-pulling tendencies. Your pet's regular daily routine, potty schedule, and comfort preferences. When your pet stays with us, they get the benefit of a dedicated, full-time care team! ❤️ Tammy I’m a lifelong dog owner and shelter volunteer who understands how stressful it can be to leave your fur-baby behind. I provide 24/7 loving, home-style care so your pet never has to deal with the stress of a commercial kennel. I have extensive experience with oral medications, all ages of pets including senior pets, and dogs with separation anxiety. Whether it's playing fetch in the yard, going on walks, or cuddling on the couch, I treat every visiting pet like family! 🏡 Jamie — House Sitting Specialist As a retiree with a lifelong passion for animals, I specialize primarily in in-home house sitting for both dogs and cats. My goal during house sits is to keep your pet's daily routine as normal and stress-free as possible in the comfort and security of their own home. I am attentive, trustworthy, and meticulous about following your exact instructions. When assisting with boarding or outdoor activities, I love taking pets for peaceful walks through nearby Kinder Farm Park or letting them explore our secure, backyard! 24/7 Full-Time Supervision: Someone is always home to monitor, feed, and interact with your pets. 100% Secure & Supervised Outdoor Play: Pups are strictly supervised outdoors and will never be left unattended. Individualized Attention: We match our daily routine to your dog's energy level, from high-energy fetch to peaceful senior relaxation. 🐾 Services Include Boarding: A safe, loving environment for your pet's home away from home. Doggy Daycare: A fun-filled day of play and socialization. Dog Walking: Give your pup the exercise and potty break they need! House Sitting: Keep your pet safe and comfortable in their own home. Drop-in Visits: Quick check-ins for feeding, playtime, or medications. We offer 24/7 support and a FREE In-Person Meet & Greet to ensure the perfect fit for your pet! We're here for YOU (and your best friend)! Advanced & Specialized Care With my professional and personal background, I am uniquely equipped to manage pets with complex health needs, including: Medical Conditions: Diabetes, blindness, neurological conditions, cardiac issues, liver disease, heart and kidney disease, and medically challenged pets. Mobility & Recovery: Specialized care for pets with limited mobility, including those recovering from or living with CCL injuries. Age Groups: Safe, patient, and tailored care for dogs of all ages including young puppies and senior dogs. Treatments: Proficient in administering oral and injectable medications. 🏡 Our Home & Safety Commitments Prime Location: Located right across from Kinder Farm Park great for engaging daily walks! 24/7 Full-Time Supervision: Someone is always home to monitor, feed, and interact with your pets. 100% Secure & Supervised Outdoor Play: Pups are strictly supervised outdoors and will never be left unattended. Individualized Attention: We match our daily routine to your dog's energy level, from high-energy fetch to peaceful senior relaxation.

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The median cost per night for house sitting in Choptank Overlook is $57

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.

How to book house sitting

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
  3. 3. Book & Pay

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Popular requests for house sitting - Choptank Overlook

Select a filter and find qualifying sitters offering house sitting.

Sitters in Choptank Overlook average 4
repeat house sitting clients

FAQs for House Sitting - Choptank Overlook

Frequently asked questions about Rover

As of November 2026, there are 412 sitters on Rover offering House Sitting across Choptank Overlook. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Choptank Overlook walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Choptank Overlook maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

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 Choptank Overlook 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!

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.

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.

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

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.

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.

Yes, you can find sitters who have experience with handling special pet needs in Choptank Overlook. 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.

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