House Sitting Kennedyville

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Kennedyville, 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: Liliana O.
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Liliana O.
from
$65
per night
5.0 out of 5 stars
• 16 reviews
3 repeat clients
10 years of experience
Chestertown, MD, 21620

“Liliana was amazing!! She kept our dogs super active and happy while we were gone and was very communicative! We would definitely book with her again!”

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Alyssa W.
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: 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: 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

“Our dog has so much anxiety and Kathleen was amazing with him! He warmed up to her with her patience and it was a great weekend! She kept us updated and in turn we had a great time away, not worrying at all. She communicates well and quickly, she kept our house clean and in great condition. We would love to have her stay and take care of our dog again. Definitely recommend her to anyone else looking.”

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Piper H.
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: Haley Z.
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Haley Z.
from
$80
per night
5.0 out of 5 stars
• 4 reviews
20 years of experience
chestertown, MD, 21678

“Haley did a great job! She was great with both my dogs and sent a bunch of pictures which was awesome! I would definitely recommend!”

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Jacob S.
Sitter Profile Image: Elexis M.
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Elexis M.
from
$55
per night
5.0 out of 5 stars
• 6 reviews
2 repeat clients
5 years of experience
DE, 19934

About: I’ve taken care of many animals throughout my teen to adult years. I volunteered at a rescue taking care of mostly the cats. I’ve previously helped rescue kittens and dogs. I’ve always had animals around me. I’m a very big animal lover. I currently have 2 cats and 2 dogs and cat sit a kitten from time to time. I give the cats baths maybe once a month and the dogs weekly and I routinely walk the dogs. I watch the dogs while they’re outside while also giving them extra love. I love taking dogs on walks. I play with cats and even bring along toys that I know my cats love.

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 was the absolute best dog sitter we could have hoped for! She was so caring and loving to both our dogs. She was especially patient with our high energy boy. Krista was incredibly flexible with our booking times as plans changed. We received daily photos and updates and knew our pups were in great hands.”

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Savannah S.
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

“Briana was early and was wonderful with my anxious dog (has separation anxiety) definitely will use her again. Can’t say enough at how great she was! You won’t be disappointed if you book her!”

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Yvonne & Joseph K.
Sitter Profile Image: Ella M.
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Ella M.
from
$55
per night
5.0 out of 5 stars
• 1 review
2 years of experience
Annapolis, MD, 21401

“Simply the best!!! Very communicative, my Karma loved their walks!! Thank you for taking care of our baby!!!!”

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Christa G.
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

“We had a great experience with Alexxis. Our dogs absolutely loved her — it was clear they were comfortable and well cared for the entire time. She was communicative, kind, and made sure to keep us updated with photos. On top of that, we came home to a spotless house, which we really appreciated. It made the whole experience stress-free. Highly recommend and would 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: 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: 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: Cynthia R.
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Cynthia R.
from
$100
per night
30 years of experience
Chestertown, MD, 21620

About: I have been born and raised to take care of any type of family member from the small lizard to largest dog to feathered friends and horses. I love all animals and I have family members of my own. Plus I have a little helper who isn't scared of anything and loves to help her momma as much as she can. I'm will to do what ever it takes to make sure everyone is a happy camper and provide the best care I can to keep your mind at ease knowing you family is in good hands. Feel free to ask me anything and if you have any special requests let me know I will do what I can to make it happen. I'll treat your kids as if they were my own. I'm currently employed part-time but I'm looking to get out of the retail business and starting my own pet sitting business where I can enjoy doing what I love. I currently live in a small apartment, so it ideal that I travel back and forth from my house to clients home. I have fur babies and a family of my own, hopefully when I get a home of my own I could introduce the doggy daycare and pet sitting at my home.

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: Bridgette M.
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Bridgette M.
from
$45
per night
8 years of experience
Viola, DE, 19979

About: I’ve been dog sitting, house sitting and dog walking for awhile up to weeks at a time. I enjoy being around all types of dogs small to big. I love getting all the puppy love!! I’m currently babysitting part-time but I can move my schedule around pretty easily and fast. I would like to pursue pet care part time as well! I have a fenced in backyard in a very quiet neighborhood. I have a dog myself. He is very lovable and doesn’t bother anyone. You tell me your feeding schedule and I will go along with it

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.

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

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  • 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.

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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

    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.
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Popular requests for house sitting - Kennedyville

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Sitters in Kennedyville average 4
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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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