House Sitting Chesapeake City

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Chesapeake City, Find top rated house sitting

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: Lita K.
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Lita K.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 3 reviews
3 repeat clients
9 years of experience
Middletown, DE, 19709

About: Hey, pet parents! I’m a proud Animal Science student at Penn State with years of experience caring for all animals great and small including dogs, cats, horses, cows, and more! With 2 dogs and 3 cats of my own, I totally get how much love our pets bring into our lives. Whether your pup needs a walk or your cat needs cuddles, I bring knowledge, reliability, and lots of tail wags. I treat every animal like family because that’s exactly what they are! As a dedicated pet owner and Animal Science student, pet care is already a major part of my daily routine! I care for my own 2 dogs and 3 cats every day, which includes feeding, walking, grooming, playtime, and managing any health or behavioral needs. I naturally structure my schedule around animal care, and it’s something I truly enjoy and prioritize. Whether it’s early morning feedings, mid-day walks, or evening cuddle sessions, caring for animals is second nature to me and I’m always happy to make space in my week to care for others’ pets with the same love and attention I give my own. When caring for pets in my own home or a client’s, I focus on creating a calm, safe, and engaging environment that matches each animal’s personality and routine. In client homes, I always follow their care instructions closely whether that’s feeding schedules, medication, preferred walking routes, or favorite toys. I keep pets on their normal routines to reduce stress and make them feel comfortable while their owners are away. For cats, I make sure litter boxes are clean, water is fresh, and they have a mix of playtime and quiet time, depending on their temperament. For dogs, I provide plenty of exercise, enrichment, and affection along with structured potty breaks and walks. I’m also experienced with senior pets and those needing medication or extra TLC. Whether I’m staying overnight, dropping in for visits, or out for a walk, I care for every pet like they’re my own attentively, gently, and with lots of love and respect!

Sitter Profile Image: Jessica C.
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Jessica C.
from
$50
per night
5.0 out of 5 stars
• 6 reviews
37 years of experience
Newark, DE, 19702

“Jessica went above and beyond to make sure our Luna was safe and happy while we were gone for the weekend! She was available and willing to meet very last minute, then all weekend provided updates to keep us at ease. She was excellent! We would highly recommend her to anyone who wants someone reliable, friendly, and amazing with dogs!”

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Erin K.
Sitter Profile Image: Rebecca R.
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Rebecca R.
from
$80
per night
5.0 out of 5 stars
• 31 reviews
17 repeat clients
8 years of experience
Townsend, DE, 19734

“Rebecca did an excellent job staying at our home with Pippin! She was really prepared with questions to help the weekend good smoothly and to understand his needs. She was very responsive to messages and sent detailed updates and pics. Our pup had a great time!”

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Leah O.
Sitter Profile Image: Michaela A.
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Michaela A.
Star Sitter
from
$80
per night
5.0 out of 5 stars
• 58 reviews
17 repeat clients
17 years of experience
Bear, DE, 19701

“Michaela was fantastic! Sent plenty of photos and updates throughout the stay and we felt so reassured knowing she was taking such good care of our dogs. House was so clean and pups were happy!”

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Lauren B.
Sitter Profile Image: Riley K.
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Riley K.
from
$38
per night
1 repeat client
4 years of experience
Newark, DE, 19711

About: I’ve taken care of family and friends’ dogs throughout the past few years. I provided whatever they needed whether that was feeding, walking, or playing. I’m currently working a part time restaurant job that never ends later than 10:30 pm. So I will have plenty of time to take care of pets overnight and during the day. I provide reliable, attentive care in my client’s homes by following routines, offering playtime and affection, administering medications as needed, and keeping owners updated regularly.

Sitter Profile Image: Jophnie W.
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Jophnie W.
from
$50
per night
5.0 out of 5 stars
• 4 reviews
2 repeat clients
1 year of experience
Newark, DE, 19702

“Jophnie has been an excellent sitter for my babies. She kept in touch with me several times a day, which I really appreciated. Everything looked great when I got home. Everything was straightened up and clean. The dogs seemed happy when I got home. Very, very satisfied!! I will definitely use her again!!”

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

“This was my second time having Terry care for my pack, and she is truly amazing. I have two dogs, Cooper and Max, and two cats, Bella and Lucky. Cooper has epilepsy and requires medication and some extra attention, so having someone I completely trust with him is incredibly important to me. Terry sent me videos and quick updates every day to let me know how everyone was doing, with extra attention to how Cooper was doing. Being able to see that everyone was happy and well cared for gave me so much peace of mind while I was away. She also pays attention to the little things. When I came home, she had left lights on and music playing for them because she knows that's what I do when I'm away. My hardwood floors looked spotless and shiny, and she even left me a beautiful candle as a gift. It was such a thoughtful way to come home. Most importantly, I came home to four happy, relaxed pets who had clearly received excellent care. Terry is incredibly caring, dependable, thoughtful, and trustworthy. I feel completely comfortable leaving my home and my animals in her care, which is priceless to me. I highly recommend Terry, and I will absolutely be using her again!”

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Tammy W.
Sitter Profile Image: Jen P.
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Jen P.
Star Sitter
from
$85
per night
5.0 out of 5 stars
• 80 reviews
22 repeat clients
25 years of experience
Middletown, DE, 19709

About: From caring for 10 senior dogs at a rescue, to bathing dogs that got sprayed by skunks, to training and taking dogs on their own outings to parks and nature hikes, you name it I’ve done it! Even flying with dogs! ✈️ I have experience with all breeds, ages, and like to keep pet parents informed with notes & pics. Growing up in farm country taught me to love and care for all animals, but dogs and cats are by far my favorite. I also have experience in administering medications to our furry friends. I left my career of being a nanny in CA to move to the east coast to marry my husband. That was 2019, and I’ve been boarding/caring for animals since then. I’m currently a stay-at-home wifey so the dogs get 100 percent of my attention when they are with us. We live in a 3 story townhouse with a small unfenced yard in front of our home, to a large grassy area on the side of our home, to a giant green grass patch directly behind us just out our back door. The neighborhood is VERY dog-friendly with lots of sidewalks and comes complete with a dog park in walking distance. Our home is dog-friendly meaning dogs are allowed on all furniture and we even have doggie steps for little pooches to get up on our bed if they wish. We also have a 2mile + walking path near us. So we have plenty of activity options. We even have Pluto cartoons for your pet to watch! Pets get 100 percent of my attention when they stay with us. Their comfort and safety is my priority as I do pet care full-time. Our home has no place that’s off limits to your pets. If they want to snuggle on our bed or relax on our couch or even be in our guest room - they are more than welcome wherever they are most comfortable. We even have a massive bean bag most animals love thinking it’s a giant dog bed 😂.

Sitter Profile Image: Brittany F.
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Brittany F.
from
$60
per night
5.0 out of 5 stars
• 20 reviews
3 repeat clients
20 years of experience
Warwick, MD, 21912

About: Welcome to Safe Hayven Fields At Safe Hayven Fields, we’ve created more than just a place for pets—we’ve created a peaceful sanctuary where every furry friend is treated like family. Nestled on our beautiful horse farm in lower Cecil County, our little slice of paradise offers breathtaking views, fresh country air, and plenty of room for adventure. Whether your pup loves splashing in the pool, running and playing in our safe, clean, and secure outdoor spaces, enjoying cozy snuggles inside, or taking a stroll to visit the horses, every day is filled with love, fun, and personalized care. We believe the most important thing we can give your pet is love. We care for each guest as if they were our own while always respecting and following every parent’s wishes, routines, and special instructions. Your pet’s happiness, comfort, and safety will always come first. Our hope is that Safe Hayven Fields becomes your pet’s home away from home—a place they’ll be excited to return to, with wagging tails and happy hearts every single visit. We can’t wait to welcome your family into ours. ❤️ My entire life revolves around my farm and caring for all of my animals. I am on the property 24/7 as this is my full time job. And luckily it’s my passion. We have a beautiful fenced in pasture with lots of space to run. We are in a very private and rural area. We also have a pool- only if parents are OK and the Pup chooses to take a dip! Your Pup will always be supervised. If there are restrictions we will always abide by them. We also have dog crates if needed or requested and a beautiful inside area as well. Basically your Pup is gonna have free range and feel a home away from home.

Sitter Profile Image: Heather W.
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Heather W.
Star Sitter
from
$70
per night
5.0 out of 5 stars
• 11 reviews
5 repeat clients
10 years of experience
Carneys Point, NJ, 08069

“Heather was great with our dogs we will definitely use her again!”

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Julia C.
Sitter Profile Image: Nicole B.
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Nicole B.
from
$32
per night
11 years of experience
New Castle, DE, 19720

About: I own dogs from puppies to Senior ,I Love and care for all pups and I know how to give medication to dogs from past history .I current live with 7 Dogs my self and I am I grooming Graduate so I have been and taken care of all different size to breed dogs I am Currently taken care if my own pups or I helping out friends and family with there pups with walking /Drop in feeding them or bathing there pups I would never make your dog feel uncomfortable or make then feel like they are not safe id rather keep them in there own home in there own space so there safe and comfortable as possible

Sitter Profile Image: Julianna B.
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Julianna B.
from
$40
per night
10 years of experience
Newark, DE, 19702

About: Hello furry parents! My name is Lily and I’m excited to support you and your family. I have worked with all dog breeds and all ages through fostering. I am currently in my training certification program to provide proper education to you and your puppers. I am an online student looking to spend my free time with amazing pets. My top priority is to give all animals time and love. Whether it’s giving a long walk, using my dog park at my complex or administering medication, I’m your girl! When I would care for your pets, it’s all about the greeting. I would love to make sure your pets are as comfortable with you as for me! If you’d love me to help them learn tricks, feel free to request!

Sitter Profile Image: Heather C.
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Heather C.
from
$55
per night
1 repeat client
3 years of experience
Georgetown, MD, 21930

About: I am a nature girl and reiki student who works mainly with animals and plants. I am also a volunteer at my local animal care shelter. Mondays & Tuesdays I am available between 9:30AM - 2:30PM. Wednesdays through Fridays, I am also available in the morning and evening. Ask about weekends - I might have availability! It is my goal to lead with care, respect and play. I am a sensitive soul and I do my best to approach each pet gently and with consideration for who they are and what they need.

Sitter Profile Image: Amber D.
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Amber D.
from
$60
per night
5.0 out of 5 stars
• 18 reviews
8 repeat clients
10 years of experience
Newark, DE, 19711

“Amber took care of my dog and cat with so much care and attention! She kept me updated and was able to easily follow my dogs routine. Absolutely would recommend her services and will be booking again!”

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Nicole G.
Sitter Profile Image: Mark & Kayleigh B.
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Mark & Kayleigh B.
from
$85
per night
5.0 out of 5 stars
• 4 reviews
10 years of experience
Bear, DE, 19701

About: Dogs have always been a big part of my life. I grew up with Border Collies and have also adopted several dogs over the years, so I'm comfortable with everything from high-energy working breeds to laid-back companions. I've also volunteered at several shelters, giving me experience with dogs of different ages, sizes, temperaments, and backgrounds. I work from home (as does my wife) so your pet will be getting consistent, attentive care. To be honest, our dog passed away last fall and we are missing the joy of being dog owners and having dogs around, but we need something a little more flexible for the time being. You are getting two sitters for the price of one and we will care for your dog as if they were our own :) As a former dog parent who has used Rover, my goal is to provide exactly what I was looking for each time I booked a walker/sitter: clear communication, limited hassle, and all of the assurances that you can rest easy and not worry...your doggo is in good hands! I work from home and call my own hours (as does my wife) so as long as we know your dog's routine we will make sure to incorporate it into our own. We have a fenced-in yard and a walking path near our home so walks are never a problem (we love walks). My wife and I both work from home so one of us will always be giving your dog attention/supervision. We have previously owned dogs who were flight risks so we have been conditioned to keep an eye out, keep doors closed, etc. We have a big fenced-in yard and have a little indoor gate/fence that we use in the house if need be to secure a hallway, etc.

Sitter Profile Image: Nathalie B.
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Nathalie B.
from
$50
per night
10 years of experience
Newark, DE, 19711

About: I’ve been taking care of animals my whole life! I’m a pre-veterinary medicine major at the University of Delaware so I’ve been studying animal behavior, nutrition, and welfare for a year now. I work as an ER veterinary assistant back home and a large animal hospital when I’m at school so I’ve gathered over 800 hours dogsitting, volunteering, shadowing vet clinics, and working. I’m passionate about taking care of your pet. :) I’m living at college which gives me a very decent amount of availability! As long as you book with me 1-2 weeks in advance, I’m available almost everyday. When caring for your pets in your home, I will follow any specials instructions or routines you give regarding feeding, exercise, and medications. I always make sure all pets feel loved, comfortable, and safe with me. I can also check the home for any issues, water the plants if needed, bring in mail/packages, and of course I will send pictures and updates!!

Sitter Profile Image: Marjorie S.
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Marjorie S.
from
$40
per night
30 years of experience
West Grove, PA, 19390

About: I have had my home base business for over 20 years and I'm looking to try something new. I have been a dog owner my entire life. I currently have 3 small dogs. I have ample time and desire to be a pet/house sitter on Rover. I love all pets, especially dogs and cats. Not a big fan of snakes. Please reach out to me, lets chat. My work is seasonal, meaning I mostly work from Spring to Fall. WIth my season coming to an end, I am looking to branch out and try something new. I have always loved animals so Rover seems like a great fit. I have a lot of free time heading into the winter. I have a 4 wheel drive vehicle so snow and ice wont stop me. I have 3 dogs. One is 13, one is 2 and the baby is 11 months. I also have 2 grown children who live at home. When I am at home working, my dogs are the shop with me. My shop is a 2 car garage and a fenced in yard. They stay outside with me most of the day with 2 breaks for naps in their private room. In the summer, they have a pool and plenty of shade. Their safely and comfort is important to me as is their need for play time, walks and lots of hugs and scratches. I am used to having a puppy around and cleaning up messes. As your pet sitter, I will never bring my dogs along with me. They have a dad at home to take care of them. My schedule is very flexible and I understand the need for help with pets. My seasonal job requires me to travel in the summer and getting pet sitters is sometimes tricky. I guess I should say, getting a trust worthy pet sitter who is going to deliver on her promises can be tricky.

Sitter Profile Image: Birol M.
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Birol M.
from
$139
per night
5.0 out of 5 stars
• 108 reviews
27 repeat clients
7 years of experience
Newark, DE, 19711

“This is the third time we’ve had Birol watch our babies and we wouldn’t go with any other sitter. He is kind, responsible and communicative. He takes great care of our older dog, Thor who is almost 14. Thor needs to be carried up the stairs and has accidents. Birol is always positive and takes great care of him. He also cares for our cat, Pearl. He sends pictures and always keeps you in the loop!”

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Maura G.
Sitter Profile Image: June S.
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June S.
from
$55
per night
4.9 out of 5 stars
• 31 reviews
12 repeat clients
12 years of experience
Kennett Square, PA, 19348

“June was great watching our two dogs and cat while staying at her house. She was flexible and reached out with questions as needed. We'll definitely be using her again in the future!”

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Katie B.
Sitter Profile Image: Alex S.
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Alex S.
from
$50
per night
9 years of experience
Middletown, DE, 19709

About: I’ve taken care of dogs since about 10 years old. My own, family, friends, and through dog sitting. I’ve taken care of puppies, senior dogs, and dogs with health issues. I work part-time, so my schedule can be flexible each week. I will have time during the weekdays and during the weekends for your pets! I will spend plenty of time giving your dog love, playing with them, and ensuring all their needs are met. I will follow exactly what you want for your dog while in your home.

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The median cost per night for house sitting in Chesapeake City is $55

Pet parents share their Rover experiences - Chesapeake City

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5.0 out of 5 stars

Sydney was a fantastic dog sitter! She was very responsible, communicative, and took great care of our chocolate lab. We will definitely hire her again!

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Rebecca D.
House Sitting
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How to book house sitting

  1. 1. Search

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Popular requests for house sitting - Chesapeake City

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Sitters in Chesapeake City average 4
repeat house sitting clients

FAQs for House Sitting - Chesapeake City

Frequently asked questions about Rover

As of October 2026, there are 1,018 sitters on Rover offering House Sitting across Chesapeake City. 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 Chesapeake City 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 Chesapeake City 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 Chesapeake City 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 , 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 .

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 .

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.

Yes, you can find sitters who have experience with handling special pet needs in Chesapeake City. On Rover:

  • 91% of sitters can help with special care needs
  • 94% 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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