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: Kathleen H.
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Kathleen H.
from
$72
per night
5.0 out of 5 stars
• 19 reviews
4 repeat clients
50 years of experience
Elkton, MD, 21921

“Such a pleasure having Kathleen take care of our pets and home when we have to be away. Firstly, our pets love her dearly and are so excited when she arrives (that they barely notice us leaving). Secondly, she is dependable to be present and to execute our requests. We have pets with medical needs and some are isolated from others. She always takes such care to give each pet the love, care, and space they each need. We found a gem with Kathleen! 😊”

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Rose S.
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: Christine S.
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Christine S.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 29 reviews
16 repeat clients
25 years of experience
Elkton, MD, 21921

“Christine was great with our dog. She made sure to follow all of our instructions and attended a meet n great to meet us and our dog. She was always communicative and sent updates/pictures while we were away. We loved having her stay with our dog!”

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Zoe H.
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

“We loved having Michaela watch our crew while we were gone! She provided regular updates, and was great handling our pets with special needs. Our house was spotless when we arrived home - we really appreciate the level of care she provided. We will absolutely be hoping to have her back when we travel in the future!”

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Lex L.
Sitter Profile Image: Nina B.
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Nina B.
from
$65
per night
5.0 out of 5 stars
• 34 reviews
15 repeat clients
5 years of experience
Middletown, DE, 19709

“Nina was great! She collected a lot of written information about our dog Daisy prior to our vacation and used it to guide her care. Nina's written log of play activities and treat rewards was remarkable and assured us Daisy was always in good hands. She updated us regularly while we were away with texts and photos. As part of our arrangement, we had requested a few extra tasks involving the watering of house plants (quite a few) and these were carried out to perfection. Not to mention, the house looked great when we returned! We will not hesitate to request our new friend and pat-sitter the next time we need to go away.”

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Mitch F.
Sitter Profile Image: Lacey S.
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Lacey S.
from
$45
per night
4.9 out of 5 stars
• 12 reviews
7 repeat clients
10 years of experience
North East, MD, 21901

“Lacey is so sweet and so loving. And she is so reliable and responsible!! Our family and our dog love her!!”

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Jenel P.
Sitter Profile Image: Alyson H.
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Alyson H.
from
$55
per night
5.0 out of 5 stars
• 3 reviews
3 years of experience
Newark, DE, 19711

About: I worked at a dog/cat kennel for over 3 years. I was fortunate enough to work with all breeds, sizes, ages, and behavioral levels. I want to give your pet the best and most comfortable experience while you're away! I am a college student at UD studying ecology. My schedule is generally pretty open with the exception of morning classes (~9 am - 11 am). My availability varies, but I can be flexible! Feel free to message me to inquire! I understand that all pets have different needs and preferences. I am comfortable playing with your dog in their home, taking them on walks, or little field trips and hikes (for the more energetic pups) around Delaware if you'd like! I have a soft spot for senior cats and dogs, so I am also more than happy to take things slower and give them the extra TLC they might need.

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: Briana B.
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Briana B.
from
$75
per night
4.9 out of 5 stars
• 18 reviews
6 repeat clients
12 years of experience
Newark, DE, 19702

“Brianna is a great sitter- listens to directions well and send lots of photos and updates! Hoping she’s available the next time I need help! Thank Brianna!!”

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Yvonne & Joseph K.
Sitter Profile Image: Clarissa O.
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Clarissa O.
from
$65
per night
5.0 out of 5 stars
• 1 review
1 year of experience
New Castle, DE, 19720

“Clarissa was fantastic! We ended up needing a last-minute person to take care of our fur baby so that we could be away for a night. Clarissa was available and willing to come to our home to meet our for baby in person before we went out of town. Then, she had great communication to keep us up-to-date while we were away. I have tremendous confidence in Clarissa and look forward to using her again. HIGHLY RECOMMEND!”

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Alexis L.
Sitter Profile Image: Ryan E.
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Ryan E.
from
$44
per night
5.0 out of 5 stars
• 5 reviews
3 repeat clients
2 years of experience
Newark, DE, 19713

“Ryan is a great guy, he was wonderful with Pluto and I would highly recommend him to anyone looking for a sitter”

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subrat s.
Sitter Profile Image: Karen D.
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Karen D.
from
$32
per night
4.9 out of 5 stars
• 178 reviews
81 repeat clients
30 years of experience
North East, MD, 21901

About: I have over 30 years in pet care industry. I Have raised , trained and shown dogs for over 15 years. I was a groomer for 10 + years. I have managed an animal shelter and took in many rescues. Pets are my life and love my job very much. I can administer medications including injections. I look forward to meeting new clients as well as caring for existing clients. I am a full time caregiver. My kids are all grown and on their own so I have plenty of time to spend with your furbaby. I have two separate fenced in yards for outdoor playtime activity. I live in a mobile home community. The entire property is privacy fenced backed with chain link for double security. There is plenty of space for all size dogs to exercise. I have the ability to spend one on one time with your pet or group play other dogs of similar temperament and size. I am experience in doggy daycare settings with 20 plus dogs at one time. I look forward to caring for your precious baby the way I would want my own pups cared for. I work from home and have a very flexible schedule that allows plenty of time to spend with your fur baby. All of our guests have a great time during their stay. Please note: If you are 30 minutes or more past your selected drop off time and you have not reached out to us we will consider this a no show. After an hour with no communication your spot will no longer be available. Communication is extremely important as is punctuatality. We plan our time based on your choices on drop off and pick up times. We do not sit around all day waiting for you to decide to show up or not. It's extremely frustrating for us when there is lack of communication. Thank you for understanding. I have a 6ft high privacy fenced in yard. I separate my personal dogs except for a couple that love to play with other dogs. We do not require meet greets. If you absolutely feel it is necessary we have a limited time slot of 15 minutes and will only accommodate if we have the availability. If you are 5 or more minutes late you will have to reschedule. We take time away from our guests and private time from our families to offer this service. Due to most dogs being temperamentally different when owners are present verses in their absence it really isn't a necessary action to determine your pups stay. I will introduce other dogs only when a new guests has become comfortable with me and my husband. Then we introduce one at a time. This can sometimes take an hour or a day depending on the individual. We require dogs to be crate trained as we crate all dogs even our own for feeding, sleeping and if we need to leave the house. We have a family member that lives in our home. He is there 24/7 so your pup is never left alone. I spend as much time out doors playing with our guests as possible,weather permitting. Indoors is more of quiet time. I do allow guest on the furniture so if that is not something permitted at please let me know. Please be aware this is MY home not a public facility. There may be crates set up in the Livingroom for current guests. I provide toys, bedding, crates and bowls. All crates have a water bucket. You will be required to provide food, treats and medications if needed No pick ups and drops off before 5:00 am and after 8:00 pm. Please schedule your dates accordingly. Please try to stick to your requested pick up and drop off times. While I am flexible I do make plans around the times you selected. If you need to change those times please try to give advance notice so I can plan accordingly. Communication is imperative to have a successful client relationship.

Sitter Profile Image: Erin K.
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Erin K.
from
$40
per night
5.0 out of 5 stars
• 3 reviews
32 years of experience
North east, MD, 21901

“Erin was amazing! She did a great job with my cat and he really loved her, and she left my apartment totally spotless. Would definitely recommend her and plan on having her watch my cat again :)”

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Hannah M.
Sitter Profile Image: Claire W.
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Claire W.
from
$50
per night
4.8 out of 5 stars
• 8 reviews
4 repeat clients
10 years of experience
Newark, DE, 19711

“Claire took great care of my dog in my home while I was away. Would definitely ask her to sit again.”

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Rachel H.
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: 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: Jennifer R.
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Jennifer R.
from
$50
per night
5.0 out of 5 stars
• 3 reviews
1 repeat client
10 years of experience
Newark, DE, 19711

About: I've always grown up surrounded by dogs, whether that was in my own household or around family. On my way to become a veterinarian, I continuously care for my own dogs, my neighbors dogs and spend my time volunteering at an animal shelter nearby, Father Johns, and ensure the health and safety of all ages of dogs. I am super excited to continue dog walking and care for your pets needs! I am currently a full time student at UD so classes may interfere but I am open to discussing times to care for your pet! Throughout my life, I've had years of experience with large dogs, senior dogs, puppies, etc. I have also had experience with many different behaviors of dogs and understand it can be hard to meet a fresh face. I will carefully comfort your pet, and introduce myself in a calm manner to ensure the safety of your pet and myself, so your pet can have a fun, relaxing time!

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: Shannon F.
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Shannon F.
from
$120
per night
16 years of experience
Newark, DE, 19702

About: I’m a caring, dependable, and attentive pet sitter / Dog owner who truly enjoys spending time with animals. I understand that every pet has their own personality, routine, and comfort level, and I take the time to make each one feel safe, loved, and cared for. I’m comfortable with feeding, fresh water, litter box care, walks, playtime, bathing, companionship, and keeping pets on their normal routine. I’m also patient with shy or nervous pets and always treat your home and your pets with respect. You can count on me to be responsible, communicative, and attentive to the little details. My goal is to give your pets loving, reliable care and give you peace of mind while you’re away.🐾❤️

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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

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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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