House Sitting Kennedyville

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Sitter Profile Image: Dawn D.
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Dawn D.
Star Sitter
from
$125
per night
5.0 out of 5 stars
• 17 reviews
5 repeat clients
12 years of experience
Crumpton, MD, 21628

About: Welcome to C & L’s Cozy Dog Retreat I have 2 pups, Chip & Lucy, ages 11 & 8, that I have raised from puppies. Many of my friends have dogs, and they frequently come over. I also enjoy riding horses when I can. I have experience working with anxious dogs & dogs in shelters also (as a volunteer). I love taking dogs for walks, playing with them, & give them attention. I limit the number of dogs I take at any given time so each pup gets lots of individual attention. You can see some of the dogs I have walked/played with in my profile pictures. I’m frequently in the Chestertown area and am more than happy to help with your pet-sitting needs. I offer drop-off and pick-up for your pups' boarding. I am available 24/7, Monday-Friday. I accept boarding and doggie daycare on a limited basis. Please message me if you are interested. This ensures I can give each pet the attention they need while ensuring safety. I am also happy to do multiple check-ins a day while your friend stays in their familiar home. I have a fenced yard and 2 friendly dogs. I can also kennel your dog if needed. A meet-and-greet with the dogs would be required before any overnight stays with us. Also, proof of immunizations.

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 was super sweet and I can tell she took great care of my boy. She stayed in my home overnight and left the place looking exactly as I left it. She even brought in my Amazon packages for me <3”

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Jennifer S.
Sitter Profile Image: Busara C.
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Busara C.
from
$65
per night
5.0 out of 5 stars
• 94 reviews
17 repeat clients
5 years of experience
Dover, DE, 19904

“Busara was a delight! She gave a lot of feedback on her time with Jasper. Jasper seemed to enjoy having her here. I’d definitely ask her to come another time!”

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Lois D.
Sitter Profile Image: Aaron W.
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Aaron W.
from
$38
per night
25 years of experience
Worton, MD, 21678

About: I have lots of compassion when it comes to animals, and I have years of experience working for cat/dog rescues as well as pet transports, I currently have a four day weekend at my current job and have way too much free time! I also have no problem with early mornings or late nights! I have two small dogs that I take for a couple walks a day, and I Help prepare their food which is home made and all natural. I also have a cat with urinary tract issues so I’m used to keeping their litter boxes spotless.

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 awesome, she was always on time when we met up, took care of Roo and the house the same way i would. House was just the way we left it. Roo definitely made a new best friend and we found out house sitter for the future, she sent us pics and updates on how things were going and she even sent pictures of the snakes. Lol. Couldn't go wrong booking with Nina if you need a house sitter, will definitely be using her in the future.”

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David C.
Sitter Profile Image: maranda c.
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maranda c.
from
$65
per night
5.0 out of 5 stars
• 17 reviews
5 repeat clients
10 years of experience
Centreville, MD, 21617

“Maranda was fantastic. I really can’t say enough positive things about our experience with her. She was quick to learn and work with the idiosyncrasies of our two cats, took care of our house which was immaculate when we returned and communicated with us while away as much/or as little as we requested. She is very personable, respectful and responsive.”

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Stephanie N.
Sitter Profile Image: Jordan M.
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Jordan M.
from
$35
per night
4 years of experience
Smyrna, DE, 19977

About: Hello everyone! I am an animal lover, I grew up around animals all my life. Our furry friends are extended family members. I hope you entrust me with your furry loved ones. I am currently an active college student, but I have somewhat situated myself with a work-life balance. I am available and flexible for weekdays and weekends! I currently have a kitten almost a year old. Having him has taught me patience, and having complete responsibility. Milo is my profile picture! I feel as though I am completely up to any challenge, I hope I can help with your furry loved ones!

Sitter Profile Image: Brigid S.
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Brigid S.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 12 reviews
3 repeat clients
18 years of experience
Queen Anne, MD, 21657

“Brigid was excellent!! She cared for my dog like he was her own. She gave him his meds on time and kept communicating with me while she was caring for him by sendings pics everyday! I would hire her again!! Thanks Brigid for taking care of my boy with love and caring for his needs!!”

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Nancy C.
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 very professional and kept me posted about the kiddos. I hope that she will sit for me again”

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Kimberly H.
Sitter Profile Image: Michael P.
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Michael P.
from
$90
per night
5.0 out of 5 stars
• 75 reviews
38 repeat clients
10 years of experience
Arnold, MD, 21012

“Michael was great with our herd. We have three pups, each with their own nuances. Michael stayed with them for a long weekend and kept us updated on their health and happiness. He was very accommodating with their needs and helped with their anxiety, and ours. We’d be glad to have him back and I think our dogs would be glad to have him back, too!”

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Jay T.
Sitter Profile Image: Heather B.
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Heather B.
from
$65
per night
5.0 out of 5 stars
• 38 reviews
14 repeat clients
18 years of experience
Wilmington, DE, 19803

“Heather was amazing and took great care of our babies, you can tell she loves animals! I also received beautiful pictures from her throughout my vacation and felt relaxed knowing they were in good hands!”

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Heather C.
Sitter Profile Image: Kee L.
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Kee L.
from
$111
per night
5.0 out of 5 stars
• 3 reviews
1 repeat client
15 years of experience
Elkton, MD, 21921

About: I've taken care of dogs of every kind since my high school days. I love caring for and building relationships with dogs because they are truly like your best friend when they get to know and love you. Currently I work from home and for the most part make my own schedule every day. I am looking to build loving relationships with every pet that I care for so every owner can confidently put their trust in me to bring their furry friends back to me anytime they need me to take care of them. Me and my husband love dogs! We have a doggy park inside of our residence as well as a lovely community of people who walk their dogs everyday I’m sure your pet will meet some friends as we go out for walks and play at the park. Please let me know if you have any special food or any other request that you need me to accommodate to ensure that your furry baby is okay so I can be prepared as much as I can to welcome them into our home. I make my own schedule every day so i am pretty much free Monday through Sunday each week. I will make sure I update the time slots that are booked as clients start scheduling their appointments. All small and medium-sized dogs will be more than welcomed to roam freely around my living room kitchen area and are allowed to sit and lay on the couches as well. The floors are hardwood so even if they have an accident of pooping or peeing on the floor it will be alot easier for me to clean up on the hard floors than the carpeted areas. They will be allowed to come into my bedroom or any other room as long as I am in the room supervising them. I will take them outside to potty every 2 hours timed from the time they arrive until their scheduled time of leaving. You can feel free to bring their favorite toys they love to play with but I will also be purchasing brand new toys that I'm sure your dogs/cats will love to play with.

Sitter Profile Image: Alexxis E.
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Alexxis E.
Star Sitter
from
$165
per night
5.0 out of 5 stars
• 36 reviews
10 repeat clients
15 years of experience
Annapolis, MD, 21409

“Alexxis was absolutely amazing with our dogs, Poppy and Beale, while we were away for the week! She took such great care of them and spent lots of time keeping them company. She even noticed when Poppy had bloody urine, acted quickly, and took her to the vet — we’re so grateful for her attentiveness and care. Alexxis administered antibiotics and kept us updated the whole time, which gave us so much peace of mind. It was clear our dogs adored her! We couldn’t have asked for a better sitter and will definitely book with her again.”

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Macey W.
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: Sharita T.
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Sharita T.
from
$25
per night
25 years of experience
Havre De Grace, MD, 21078

About: I am a mature and reliable pet sitter with a preference for cats but will also be happy to provide care for small dogs or other animals. I operate with a genuine love for all all animals and have a history of community service and donations to animal shelters and causes. I have been a cat owner for over 12 years and currently have one senior cat. When it comes to cat care, my extensive experience and commitment to feline companionship shine through. I specialize in socializing skittish cats, exercising larger cats, and soothing senior cats. I am detail-oriented, ensuring that your pets get the care and attention they are accustomed to, including medication management, grooming, and in-home care. I am proactive in communication and am also highly responsive, giving pet-owners piece of mind. But that's not all – my versatility extends to caring for dogs as well. I bring the same level of dedication and expertise to canine companions, ensuring they receive the love and attention they deserve. Whether it's daily walks, playtime, or adherence to dietary requirements, I'm well-equipped to provide comprehensive care for dogs of smaller sizes. With me as your trusted pet sitter, you can confidently leave both your cats and dogs in capable hands. Your pets' happiness, safety, and well-being are my top priorities, and I take pride in delivering exceptional care tailored to their individual needs, whether they're four-legged felines or canine companions. My schedule is flexible and can accommodate most requests with enough notice. While I can provide care for your pet in your own home, I am also available to host your pet in my home. I have a one-level home with hard wood floors (for easy cleanup) and pet-proof furniture. I do not let animals outside unattended so if you have a cat that likes to wander outside, I will not be comfortable allowing that

Sitter Profile Image: Cole H.
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Cole H.
from
$75
per night
5.0 out of 5 stars
• 16 reviews
3 repeat clients
20 years of experience
Wilmington, DE, 19801

“Cole was spectacular with our older basset hounds. He was able to get both of them on walks (not easy with one being a little grumpy with new people). Both dogs while happy to see us, didn’t seem like they had been stressed while we were away- a big improvement for us! Cole also kept our home on great order, dealt with a clogged sink, and even watered my plants (without me asking!). We can’t wait to use him again for future times away- the boys seemed to enjoy his presence.”

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Matthew A.
Sitter Profile Image: Cody Y.
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Cody Y.
from
$35
per night
15 years of experience
Magnolia, DE, 19962

About: I grew up with dogs and have always considered them part of the family. Until last year, I cared for my own dog, Tank, who passed away at 14. Caring for him through his senior years taught me the value of patience, close observation, and keeping a pet’s routine as comfortable and consistent as possible. Tank occasionally had seizures, which gave me firsthand experience remaining calm, reducing stimulation, helping keep a dog safe from injury, and closely monitoring them while following an owner’s or veterinarian’s instructions. I understand that every pet has their own needs, personality, routines, and comfort level. I’ve also dog sat for family members and truly enjoy making sure their pets receive dependable care, affection, exercise, and companionship while they are away. I’m detail-oriented and will follow your instructions closely. Feeding schedules, walking routines, medications, and house rules to favorite toys, training cues, and any special needs, your pet will feel safe, loved, and cared for in your absence. I work part-time as a caregiver for a person with a disability, a role that has strengthened my patience, reliability, and attention to individual routines and needs. Because my schedule is flexible, I can accommodate a wide range of pet-care routines, visit times, and scheduling needs. Whether I’m caring for your pet in my home or yours, I focus on keeping their routine safe, comfortable, and as familiar as possible. At my home, I have a yard available for regular bathroom breaks and a small park nearby for daily walks, exercise, and fresh air. I do not have any pets living with me full-time. From time to time, I care for my mother’s friendly French Bulldog, Vinny, who enjoys being around other dogs. I will always communicate in advance if another dog may be present and will make sure introductions are handled slowly, safely, and according to your pet’s comfort level. In a client’s home, I will follow your instructions closely regarding feeding, walks, playtime, medications, house rules, and any special routines or needs. My goal is to provide dependable, detail-oriented care that helps your pet feel secure and well cared for while you are away.

Sitter Profile Image: Jared F.
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Jared F.
from
$40
per night
20 years of experience
Newark, DE, 19702

About: I mostly took care of my dog and my sisters dog growing up. She has relied on me to walk, feed, and bathe her dog while she was away on business trips and vacations. I would love to help you too. I currently work full time, but there will be plenty of time after work and on weekends to play with and take care of your dog. I have a fenced yard and a friendly dog to keep your fur baby company. I can easily crate your dog if need be. We will all get along just fine.

Sitter Profile Image: Laila F.
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Laila F.
from
$27
per night
5.0 out of 5 stars
• 3 reviews
6 years of experience
Columbia, MD, 21044

“Laila is amazing!! I had a very last minute cancellation, but Laila saved the day! After a video call I was confident that my dog would be well cared for while I was away. She was a great communicator and kept me updated throughout the stay. I appreciate her so much for her help!!”

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Brenna M.
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The median cost per night for house sitting in Kennedyville is $50

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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

How to book house sitting

  1. 1. Search

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Popular requests for house sitting - Kennedyville

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Sitters in Kennedyville average 4
repeat house sitting clients

FAQs for House Sitting - Kennedyville

Frequently asked questions about Rover

As of October 2026, there are 1,916 sitters on Rover offering House Sitting across Kennedyville. 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 Kennedyville 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 Kennedyville 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 Kennedyville 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 Kennedyville. On Rover:

  • 89% of sitters can help with special care needs
  • 94% can help with giving oral medications or injections
  • 96% 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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