House Sitting Oak Orchard

Find a loving house sitter to watch over your pets and your home.

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Over 11
pet parents in Oak Orchard have booked house sitting

Oak Orchard, 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.

1 / 1
Sitter Profile Image: Madison W.
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Madison W.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 20 reviews
3 repeat clients
2 years of experience
Millsboro, DE, 19966

“I must absolutely RAVE about Madison because she took such amazing care of our pets with incredible, consistent communication! Extra special shout-out because our dog, unfortunately, got sick while under Madison's care, and Madison kept me informed of our dog's behavior, current status, and cleaned up all of the messes so thoroughly! We love her and I HIGHLY recommend her!!!❤️”

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Kelli C.
Sitter Profile Image: Jasmine H.
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Jasmine H.
from
$60
per night
5.0 out of 5 stars
• 5 reviews
6 years of experience
Millsboro, DE, 19966

“Jasmine was fantastic with our two boys! She was very responsive and arrived on time. She provided helpful updates throughout the day, which we truly appreciated. We also appreciate her time and attention she gave to our dogs.”

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Dena T.
Sitter Profile Image: Michael E.
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Michael E.
from
$28
per night
37 years of experience
Long Neck, DE, 19966

About: I have owned dogs and cats my entire life. Additionally, I have volunteered time with professional trainers, learning tips and tricks along the way. I love them all the way from pups to grey hairs. I am a realtor, so I am set my own schedule daily. This will allow me to easily help with your fur-baby any day of the week. Happy to stay in your home so that your pet doesn't get disturbed by an environment change. I can easily transport them to any vet should there be a need for emergency services.

Sitter Profile Image: Max E.
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Max E.
from
$60
per night
5.0 out of 5 stars
• 2 reviews
40 years of experience
Georgetown, DE, 19947

About: I have had many dogs and cared for many others. It is a true labor of love for me and something I really love doing. I’m retired so my schedule is super flexible. Whatever your schedule I can probably accommodate it. Give me a try and let’s see if we can work it out. I love them but I don’t board dogs (sorry). Couldn’t negotiate that successfully with my wife. I do love spending time with them on walks or in your home.

Sitter Profile Image: Lauren C.
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Lauren C.
from
$28
per night
15 years of experience
Ocean View, DE, 19970

About: I’m a lifelong animal lover who believes pets deserve their own little staycation while you’re away! Whether it’s a neighborhood walk, some backyard playtime, belly rubs on the couch, or simply keeping them company, I’ll make sure your pet feels happy, comfortable, and loved. I’m dependable, attentive, and happy to stick to your pet’s normal routine — meals, walks, medications, playtime, and all the extra snuggles they’ll allow. I’ll also send plenty of photo updates, so you can relax knowing your furry family member is being well cared for and getting lots of love while you’re gone. 🐾 My schedule is flexible as my husband is a business owner and I work part-time for him, which gives me plenty of time to work pet care into my day. I’m happy to plan visits, walks, feeding times, and check-ins around your pet’s normal routine whenever possible. Whether you need occasional help, vacation coverage, or regular visits, I’ll do my best to make things easy and stress-free for both you and your pet. 🐾 Your pet’s safety, comfort, and routine will always come first. I’ll carefully follow any instructions you provide for feeding, walks, medications, doors or gates, and anything else that helps your pet feel secure. I’m also very respectful of your home and belongings and will keep you updated with photos and messages, so you always know how your pet is doing. My goal is for you to come home to a happy pet and a home just as you left it. 🐾

Sitter Profile Image: Dina B.
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Dina B.
from
$60
per night
5.0 out of 5 stars
• 7 reviews
1 repeat client
10 years of experience
Berlin, MD, 21811

“Highly recommend. Was very good with my two dogs and great communication.”

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Justin W.
Sitter Profile Image: Courtney R.
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Courtney R.
from
$28
per night
10 years of experience
Millsboro, DE, 19966

About: I have been a lifelong dog owner and have previous paid experience caring for pets. Through both personal and professional experience, I understand that every pet has its own unique personality, routine, and needs. I have experience feeding, walking, playing with, and providing companionship to dogs, as well as ensuring they receive plenty of attention, exercise, and love while their owners are away. As a special education teacher, I am patient, responsible, dependable, and detail-oriented. I am comfortable following detailed care instructions, maintaining consistent routines, administering basic medications if needed, and keeping owners updated with messages and photos for peace of mind. I treat every pet as if they were my own and strive to provide a safe, loving, and stress-free experience for both pets and their families. My availability is flexible. During the school year, I am available before and after school, evenings, weekends, holidays, and for overnight pet sitting. I do my best to accommodate last-minute requests whenever possible. Please feel free to reach out to discuss your pet care needs. Your pet’s safety, comfort, and happiness are always my top priorities. I understand that trusting someone with your furry family member is a big decision, and I take that responsibility seriously. I carefully follow each pet’s routine, including feeding schedules, exercise, medications, and any special instructions you provide. I believe in creating a calm, loving, and stress-free environment where pets feel safe and cared for while you’re away. As a pet owner myself, I know the importance of regular communication, so I’ll provide updates and photos to give you peace of mind. You can count on me to treat your pets with the same love, patience, and respect that I give my own.

Sitter Profile Image: Ryan M.
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Ryan M.
from
$50
per night
20 years of experience
Millsboro, DE, 19966

About: Good afternoon,I am a current k-9 handler with a certified police K-9. I’m looking to provide a service and continue to help clients in my spare time. I can train your dog in obedience, tracking, and scent work. If you have any questions please ask. I work nights so my availability is extremely flexible. We will go over your wants and needs in detail before scheduling the first visit. Thanks I will care for the clients dogs and animals as if they were my own family with much respect. Dogs are extensions of people’s family’s.

Sitter Profile Image: Cole H.
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Cole H.
from
$80
per night
5.0 out of 5 stars
• 16 reviews
3 repeat clients
20 years of experience
Lewes, DE

“My senior dog took an immediate liking to Cole, always a good sign, and Cole was adept at administering to his particular needs, including giving medication and nudging him outside when he was reluctant to move. I've already requested that Cole come again!”

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Carol P.
Sitter Profile Image: Brooke C.
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Brooke C.
from
$75
per night
10 years of experience
Lewes, DE, 19958

About: I have always been a pet lover ever since I can remember! Growing up, my family has had golden retrievers, cocker spaniels, shih tzus, and my family now has a labradoodle, but I absolutely love all dogs! My sister has also had pet bunnies that are the cutest. I would love to have a dog right now, but at the moment I would love to help others with their pet sitting needs. Please reach out! I’m a high school teacher, so I’m currently looking to pet sit only at clients’ homes mainly on weekends or nights during the week! I provide a safe, loving, and reliable environment by following each pet's normal routine as closely as possible, including feeding schedules, walks, playtime, medications, and any special care instructions. When I am caring for a pet at a client’s home, I make sure they receive plenty of attention, affection, and supervision while keeping their environment clean and secure. I also keep pet parents updated with messages and photos so they can feel confident knowing their pet is happy and well cared for!

Sitter Profile Image: Shelby H.
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Shelby H.
from
$50
per night
16 years of experience
Millsboro, DE, 19966

About: I’ve spent my entire life around dogs, and have helped care for my family’s four legged friends for as long as I can remember. I’m no stranger to walking, feeding and cleaning up after dogs of all shapes and sizes. As a teenager, my neighbors and friends entrusted me to care for their pets. Whether they were going to be home from work late and needed someone to walk their dog or were going out of town for a weekend, I was there to help. No matter your dog’s age, size or energy level, I am confident I can provide the best possible care for them! I am currently working remotely so I am available to care for your pups at any hour of any day! From early mornings to late nights, I will be there. At home, I have a fenced in yard where my dogs are able to run and play free, but I also make sure they get plenty of leash walks around the neighborhood. Regardless of your home/ yard’s set up I can ensure your pup will get the best possible care.

Sitter Profile Image: Jarren C.
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Jarren C.
from
$28
per night
15 years of experience
Frankford, DE, 19945

About: Ive been taking care of little to small pups ever since a little girl. Our family has had breeds anywhere from chihuahuas to lab to boxer. Im looking forward to meeting new pups, as well as giving them the exercise and cuddles they need or desire. If you have any specific questions or concerns, please feel free to reach out anytime! I love puppies, so anytime is puppy time. But, I'm currently available only early mornings, mid day and evenings. I do have a child at home so that will have to be taken into consideration. I work a 8-4 schedule, but I am free to leave if I absolutely need to. I can definitely do grooming. Your pet will be fed based on owners normal schedule. Dogs can be let out ever 2-6 hours depending on availability. Any rule you apply for your pet to adhere to, I will delegate that.

Sitter Profile Image: Heather B.
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Heather B.
from
$125
per night
5.0 out of 5 stars
• 6 reviews
1 repeat client
30 years of experience
Berlin, MD, 21811

“Heather is the only sitter that could get Arthur out from under the table! She’s the best!”

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Julie P.
Sitter Profile Image: Chelsea R.
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Chelsea R.
Star Sitter
from
$100
per night
5.0 out of 5 stars
• 12 reviews
4 repeat clients
12 years of experience
Frederica, DE, 19946

“Krose had a great day with Chelsea! Chelsea arrived early with a goodie bag with treats and a toy. We appreciated the photos throughout the day. We were happy to see he was relaxed when we arrived home. We would definitely use Chelsea again!”

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Jeanne S.
Sitter Profile Image: Catherine H.
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Catherine H.
from
$200
per night
38 years of experience
Seaford, DE, 19973

About: Building Trust with Pets • Peace of Mind for Their People • Loving • Reliable • Personalized • Attentive • Compassionate • Trustworthy • Gentle • Patient • Experienced • Enriching • Dependable • Safe • Professional • Nurturing • Heartfelt Pet care is a natural part of my daily routine. I intentionally schedule my days to provide dependable visits, walks, playtime, feeding, medication (if needed), and plenty of one-on-one attention. I enjoy staying active, so walks and outdoor time are something I genuinely look forward to. I treat every pet like a member of my own family and make sure they receive consistent, loving care while you’re away. I care for pets in their own home where they’re most comfortable and their routine stays consistent. I follow each owner’s instructions carefully for feeding, fresh water, walks, playtime, medications, and any special needs. I also spend quality time providing companionship, affection, and enrichment—not just completing a checklist. During each visit, I make sure the home is secure, clean up after the pet, and send updates with photos so owners know their pet is happy, safe, and well cared for.

Sitter Profile Image: Hannah H.
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Hannah H.
from
$40
per night
5.0 out of 5 stars
• 14 reviews
4 repeat clients
1 year of experience
Milford, DE, 19963

“Hannah was an awesome sitter for our dogs and cats! She sent great pics and videos, easer our anxiety, and took care of the home as well. I would highly recommend her based on how the animals responded to her, her communication, and her niceness.”

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Rachel H.
Sitter Profile Image: Alyssa M.
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Alyssa M.
from
$20
per night
4.5 out of 5 stars
• 2 reviews
2 repeat clients
12 years of experience
Seaford, DE, 19973

“Alyssa was great with our fur babies, and sent pictures often while we were away. You could tell the pups were happy by the big smiles on their faces in every picture! We will definitely be asking Alyssa to watch them the next time we go away.”

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Jennifer S.
Sitter Profile Image: angel D.
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angel D.
from
$25
per night
5.0 out of 5 stars
• 1 review
26 years of experience
Westover, MD, 21871

“This was my first time using Rover and I believe Angel’s as well. She was great at communicating and sending me updates and handled a few extra things during my time away. She was very respectful of my home and my dogs really enjoyed her company. I would definitely feel comfortable using her again.”

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Steven M.
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The median cost per night for house sitting in Oak Orchard is $60

Pet parents share their Rover experiences - Oak Orchard

1 / 1
5.0 out of 5 stars

Neena did an amazing job with caring for our cat. She sent many pictures and updates and has great communication all around. We would definitely hire her again!

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Jenna C.
House Sitting
5.0 out of 5 stars

Jennifer took great care of our pups while we were away. We came back to two happy doggies. She was great with updates throughout the weekend and was so very kind. We would love to use her in the future!

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Heather W.
House Sitting
5.0 out of 5 stars

Kailee takes great care of our girls. They aren’t stressed when we arrive home. She communicates scheduling conflicts so solutions can be worked out. She leaves our home tidy. When Kailee takes care of our girls we don’t worry when we are away.

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Alynda P.
House Sitting
5.0 out of 5 stars

Madison was wonderful! House sat+watched our two golden doodles for a few days. When one of them wasn’t cooperative going potty, she tried lots of different things. Very communicative. Would recommend her to anyone looking for a dog sitter.

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Taylor W.
House Sitting
5.0 out of 5 stars

Jacob did a wonderful job caring for Oatmeal while staying overnight in our home. Jacob arrived on time and stayed beyond the required time. Photos and update text messages were provided. I will definitely keep Jacob as our primary dog caregiver whenever the need arises.

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Mark C.
House Sitting
5.0 out of 5 stars

Meghan is fantastic! She took exceptionally good care of our senior pup for over a week. We came home to a very happy and healthy pup (and also a clean house!). Couldn’t ask for better communication, including daily photos, or a more responsible pet sitter. Highly recommend Meghan!

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Alison T.
House Sitting
5.0 out of 5 stars

Blair was awesome! Took excellent care of our boys, followed our crazy instructions and even sent pics and videos the entire time. I would highly recommend her, but we don't want her stolen from us! :)

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Bobby L.
House Sitting
5.0 out of 5 stars

Carmen was wonderful with Abby. She sent pictures while we were away and kept in touch. Abby was comfortable with Carmen and all went well. Highly recommend Carmen, she stayed at our house over night and I felt at ease knowing everything was good.

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Suzanne R.
House Sitting
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How to book house sitting

  1. 1. Search

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Popular requests for house sitting - Oak Orchard

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Sitters in Oak Orchard average 3
repeat house sitting clients

FAQs for House Sitting - Oak Orchard

Frequently asked questions about Rover

The average cost of House Sitting in Oak Orchard is $44 per night as of October 2026. Most bookings cost between $25 and $69 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 284 sitters on Rover offering House Sitting across Oak Orchard. 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 Oak Orchard 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 Oak Orchard 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.

<b>Tip:</b> 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 Oak Orchard 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 Oak Orchard. On Rover:

  • 92% of sitters can help with special care needs
  • 95% 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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