House Sitting Oak Orchard

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

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Over 5
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: Kailee D.
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Kailee D.
from
$60
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
9 years of experience
Millsboro, DE, 19966

Kailee took wonderful care of Blossom and Beanie. Our girls weren’t stressed at all when we arrived home. She left our home immaculate. We definitely hope to use her again. Both girls give Kailee 5 paws!

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Alynda P.
Sitter Profile Image: Chelsea-Rose L.
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Chelsea-Rose L.
from
$50
per night
5.0 out of 5 stars
43 reviews
15 repeat clients
10 years of experience
Lewes, DE, 19958

Chelsea was wonderful, we booked her last minute after a family member became ill and could not sit our dog, Kenzie. She stayed over night and sent pictures and updates. I felt very confident leaving our home and dog in her care. Will definitely use her again.

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Marshall B.
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: Jessica L.
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Jessica L.
from
$33
per night
5.0 out of 5 stars
8 reviews
2 repeat clients
10 years of experience
Millsboro, DE, 19966

Jessica was wonderful with Kenzie and kept us informed with lots of pictures and feed back. Would highly recommend and use again in the future.

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

She was amazing with our Annabel!

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Rachael I.
Sitter Profile Image: Stacy P.
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Stacy P.
from
$60
per night
5.0 out of 5 stars
2 reviews
40 years of experience
Long Neck, DE, 19966

Stacy went beyond my expectations. She communicated daily and sent pictures and videos. She wrote down Mia's daily routine. Stacy left my home perfect. I know Mia was very well cared for. I would highly recommend Tracy.

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Julie G.
Sitter Profile Image: Gabrielle P.
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Gabrielle P.
from
$70
per night
5.0 out of 5 stars
2 reviews
5 years of experience
Lewes, DE, 19958

Gabrielle did a wonderful job taking care of our 3 dogs for an overnight visit. We have one very nervous little boy, an energetic “middle child,” and a slow, super-senior female. Pleased to say we came home to 3 happy dogs!

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Dana H.
Sitter Profile Image: Aubrey J.
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Aubrey J.
from
$80
per night
5.0 out of 5 stars
23 reviews
10 repeat clients
5 years of experience
Georgetown, DE, 19947

Aubrey was great with Brunson while we were on holiday. He was well cared for and he’s a puppy who still wakes up in the middle of the night. Aubrey was patient and loving.

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Ame S.
Sitter Profile Image: Megan W.
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Megan W.
Star Sitter
from
$125
per night
5.0 out of 5 stars
29 reviews
6 repeat clients
21 years of experience
Lewes, DE, 19958

Megan was fantastic! She provided regular updates, photos and videos about our girl while we were away. This was the first time we’d been away from Joy for over a week and we will certainly contact Megan again when we’re away in the spring.

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John F.
Sitter Profile Image: Ryan C.
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Ryan C.
Star Sitter
from
$90
per night
5.0 out of 5 stars
39 reviews
6 repeat clients
5 years of experience
Lewes, DE, 19958

Ryan is awesome! Sent photos/videos everyday. Went above and beyond to make sure my pups were taken care of and both their stress and mine was minimal. My home looked the same if not better then I left it. We would HIGHLY recommend Ryan. Ryan, thank you. We appreciate you!

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noreen k.
Sitter Profile Image: Carolyn G.
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Carolyn G.
from
$38
per night
5.0 out of 5 stars
17 reviews
1 repeat client
10 years of experience
Lewes, DE, 19958

"We had the pleasure of having Carolyn as our pet sitter, and she was absolutely outstanding! From the moment she arrived, our pets, including our usually shy one, were drawn to her warmth and affection. They quickly became comfortable and were even snuggling with her in no time. Carolyn was incredibly attentive, taking them on several enjoyable walks each day, which they absolutely loved. Additionally, she went above and beyond by keeping our home spotlessly clean, leaving it in pristine condition upon our return. We highly recommend Carolyn to anyone in need of a reliable, caring, and exceptional pet sitter. She truly cares for your pets as if they were her own

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Kara C.
Sitter Profile Image: Jacqueline & William C.
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Jacqueline & William C.
Star Sitter
from
$100
per night
5.0 out of 5 stars
226 reviews
100 repeat clients
8 years of experience
Millsboro, DE, 19966

Jacqueline took care of our dog and two tree frogs for us. She was very pleasant and seemed to bond well with our dog. She was wonderful and flexible re: adding the frogs into the mix.

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Deborah M.
Sitter Profile Image: Brooke W.
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Brooke W.
from
$50
per night
5.0 out of 5 stars
21 reviews
1 repeat client
25 years of experience
Millsboro, DE, 19966

Brooke is a wonderful pet sitter! Amigo is a rescue and had a sad beginning so he is sometimes withdrawn around strangers but he immediately loved Brooke! She is so reliable and shows up on time and lets you know her schedule in advance. She is great with animals and a very sweet person. She is very smart and catches on quickly. Reluctantly highly recommend her because if everyone uses her she might be too busy when we need her next and I definitely want her the next time we need a sitter!

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Patricia N.
Sitter Profile Image: Michael J.
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Michael J.
from
$75
per night
5.0 out of 5 stars
1 review
16 years of experience
Dagsboro, DE, 19939

Michael made sure my animals were well cared for. Will definitely use again.

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Steve M.
Sitter Profile Image: Marilyn & Mark W.
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Marilyn & Mark W.
from
$75
per night
5.0 out of 5 stars
23 reviews
2 repeat clients
40 years of experience
Lewes, DE, 19958

Marilyn was so communicative, sent us daily updates and photos, and really cared for our dog Theo! We ran into some challenges during her stay which she handled expertly and with so much care. We would book her over and over and highly recommend her.

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Jalene G.
Sitter Profile Image: John B.
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John B.
from
$95
per night
20 years of experience
Harbeson, DE, 19951

About: Ive had dogs in my family ever since I was a kid. I have a 10 year old pit mix, a 13 year old husky, and a 1 year old husky, so I know how to care for multiple dogs at once and dogs of all ages, including puppies. I will care for your dog the way you would. I will take them on as many walks as youd like, and treat them as if they were my own. I get along very well with all dogs and I have plenty of experience. I dont trust my dog with just anybody, so I know how important it is to build that trust with your dog and to not change their comfortability and routine. I work from home, so I am free for as many walks or as much play time as needed! I am available all day every day, and your dogs will be my first priority. I can go on as many walks as needed, depending on the age and activity level of your dog. I have experience crate training my own dog if you need me to do that. I will care for your dog the same way as if youve never left.

Sitter Profile Image: Julie M.
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Julie M.
from
$50
per night
5.0 out of 5 stars
24 reviews
5 repeat clients
5 years of experience
georgetown, DE, 19947

Julie was amazing! Our pets were very well care for while we were gone. We came home to a house that was in as good, if not better shape than when we left. She communicated with me any time I requested and in a timely manner. I felt good knowing they were well cared for while we were gone. Oh, she even washed the sheets on the bed she used. Great service for sure!

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Kelly C.
Sitter Profile Image: Tara L.
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Tara L.
from
$54
per night
5.0 out of 5 stars
3 reviews
1 repeat client
30 years of experience
Millsboro, DE, 19966

Tara was wonderful, thoughtful, and mostly a dog lover. Aubee was well cared for. We appreciate her and would highly recommend her.

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michele m.
Sitter Profile Image: Cole H.
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Cole H.
from
$92
per night
5.0 out of 5 stars
16 reviews
3 repeat clients
20 years of experience
Lewes, DE

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: Sierra W.
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Sierra W.
from
$70
per night
4.9 out of 5 stars
28 reviews
12 repeat clients
7 years of experience
lewes, DE, 19958

Awesome communication. Many pictures of my dog throughout the day. House was left better then when she arrived. Will be using again. Highly recommend.

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Jesse H.
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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

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

Stacy went beyond my expectations. She communicated daily and sent pictures and videos. She wrote down Mia's daily routine. Stacy left my home perfect. I know Mia was very well cared for. I would highly recommend Tracy.

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Julie G.
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
1 / 1
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Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • 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?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

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

Meet local sitters who will treat your pets like family

  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
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Popular requests for house sitting - Oak Orchard

Select a filter and find qualifying sitters offering house sitting.

Sitters in Oak Orchard average 4
repeat house sitting clients

FAQs for House Sitting - Oak Orchard

Frequently asked questions about Rover

The average cost for House Sitting in Oak Orchard on Rover is $44.4 per night (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .

As of August 2026, there are 291 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.

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 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 Rover Guarantee , 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 Rover's Trust & Safety page .

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 short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works 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:

  • 93% of sitters can help with special care needs
  • 97% can help with giving oral medications or injections
  • 100% 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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