House Sitting Winding Brook Village

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pet parents in Winding Brook Village have booked house sitting

Winding Brook Village, 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: Jenni L.
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Jenni L.
from
$75
per night
5.0 out of 5 stars
196 reviews
79 repeat clients
15 years of experience
Newark, DE, 19711

Jenni was great with our 5 dogs. She would updates and pictures every day. Even got a video. Everything went smoothly. We will definitely use them again. I would highly recommend her.

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Robyn P.
Sitter Profile Image: Brice B.
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Brice B.
from
$50
per night
5.0 out of 5 stars
8 reviews
1 repeat client
14 years of experience
Newark, DE, 19702

Brice was a fantastic sitter for our dog! She kept us updated and informed throughout her time with him. She was very attentive and took amazing care of him. We would definitely hire Brice again!

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Rebecca D.
Sitter Profile Image: Kathleen K.
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Kathleen K.
from
$32
per night
20 years of experience
Elkton, MD, 21921

About: I have been around and taken care of different pets since I was young. Often I pet/house sit for family/friends while they are on vacation but I have recently started watching dogs in my own home while the owners are away. I have watched dogs ranging from Cane Corso to Shih Tzu as well as several cats, hamsters and fish. I prefer to pet sit in the owners home so the pets are less stressed but will do everything I can to make them feel comfortable in my own home. I live on 4 acres that are not fenced in so if you or your dog are not okay with that I will make sure they are leashed anytime they are outside. I do have cats but they are in a separate part of the house where your pet will have no access with. I am always open to any questions or suggestions! I work full time typically from Monday to Friday. It’s usually 8-4 but can range from 4am to midnight. I will always let you know ahead of time what my schedule is or if you require something specific I’m willing to try to work something out. I have a lab that is crate trained if your dog is lonely they can go together or be in crates next to each other. The dogs will also never be alone or outside together without supervision. As for your own home I have no issue with pictures/FaceTime or cameras being in the house. I have a law enforcement background and my only concern is to care for your pets and make sure the house is secure when I leave.

Sitter Profile Image: Kathleen H.
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Kathleen H.
from
$72
per night
5.0 out of 5 stars
17 reviews
3 repeat clients
50 years of experience
Elkton, MD, 21921

Kathleen did a wonderful job taking care of our animals (3 dogs) and did some extra cleanup for us. She sent us pics and took some extra time to not only watch after the guinea pigs, hamster and mouse, but even cleaned out their stinky cages. It was obvious that the dogs were comfortable with her. Thanks Kathleen. We appreciate all you did for us.

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Stephen W.
Sitter Profile Image: Jonaika W.
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Jonaika W.
from
$45
per night
5.0 out of 5 stars
8 reviews
3 repeat clients
5 years of experience
Bear, DE, 19701

Jonaika did a great job caring for Boston. She sent me photos of what he was doing and that made me comfortable. Boston enjoyed her company and I would definitely use her again!

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Donna B.
Sitter Profile Image: Megan R.
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Megan R.
Star Sitter
from
$75
per night
5.0 out of 5 stars
113 reviews
40 repeat clients
15 years of experience
Lincoln University, PA, 19352

Megan was great! Followed instructions, sent pictures, and took very good care of our little Larry while we were gone. We'd definitely hire Megan again!

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Angela L.
Sitter Profile Image: Michaela A.
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Michaela A.
Star Sitter
from
$80
per night
5.0 out of 5 stars
56 reviews
16 repeat clients
17 years of experience
Bear, DE, 19701

SUPER🤩 This was our first time using Michaela, and she was absolutely wonderful! She watched our 5 year old lab at our home for a week and did a fabulous job with her. Cali is a very active and energetic lab. She followed her schedule and met Cali’s needs. Michaela made sure that her needs were met by getting her outside a few times during the day to play fetch with her frisbee and tennis ball, along with taking her on her walks. And not only that, Cali has a bit of anxiety at times and Michaela made sure she was loved and got the attention she needed while we were away. Michaela did check-ins and sent pictures daily( morning and evening). Michaela is very professional, caring and super friendly plus, she actually had more questions for us about Cali then we did for her, which was super impressive. She took notes about Cali starting with what her daily routine is like, her eating schedule, activities she likes, her behaviors etc. You name it, she asked it. My husband and I just knew after meeting with her, that she would be perfect taking care of Cali because you could just tell that she genuinely cares about your pet and their needs. We also felt super comfortable allowing her care for Cali and be in our home. We were so happy to find a kind, friendly, professional and trustworthy person to take care of Cali. Also, I am a bit of a clean freak and I can tell you, that my house was left the same way I left it….looked like she was never there, spotless! We were also having bad storms while we were away, so I texted Michaela about a few outside things on our deck that needed to be taken care of and she made sure it was all taken care of as well. A breaker tripped while she stayed with Cali, so she texted us the issue and we were able to call her and help get it resolved. Like I said before very professional, caring and kind. Her communication and dedication of care not only for our dog but our home was truly amazing. We will definitely be using Michaela’s services again and highly recommend.

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

What can I say about Christine? She was a godsend! After losing my beloved dog, I wanted to adopt another one after my family vacation. But when I saw my current puppy up for adoption, I immediately fell in love with him because he reminded me of my previous soul dog. I applied for adoption, and the shelter approved us. They allowed us to adopt my beloved Charlie if we could find a reliable dog sitter to watch him while I was away. I picked up Charlie just 2 days before my trip, and I was really worried about my brand-new, scared little puppy. But Christine went above and beyond with my baby. She stayed at my house with him the whole time, took great care of him, and gave him so much love. During my trip, she noticed he was coughing and even offered to take him to my vet — and she did. I highly recommend Christine to anyone looking for someone with the gift of caring and giving genuine love to your best friend :)

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Jessica K.
Sitter Profile Image: Alexis C.
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Alexis C.
from
$33
per night
10 years of experience
Newark, DE, 19711

About: I have taken care of many animals and give the best care I can while sharing pictures and updates to the owner. I can work with food motivated animals to do simple tricks. I am starting college shortly but I still will dedicate as much time as I can to taking care of animals. Breaks and days I don't have classes will be for anyone needing pet care! I have a car and can go to clients' houses and take care of their pets, as I have done often for friends and neighbors. I have a partially fenced yard for leashed play. I am in a house under construction but the top floor is finished and houses my two kittens. Calmer dogs would be better if coming into my house, otherwise I am able to care for any size or personality in the owners house.

Sitter Profile Image: Jophnie W.
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Jophnie W.
from
$45
per night
5.0 out of 5 stars
3 reviews
1 repeat client
1 year of experience
Newark, DE, 19702

Jophnie has been an excellent sitter for my babies. She kept in touch with me several times a day, which I really appreciated. Everything looked great when I got home. Everything was straightened up and clean. The dogs seemed happy when I got home. Very, very satisfied!! I will definitely use her again!!

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Helene W.
Sitter Profile Image: Elisa H.
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Elisa H.
from
$50
per night
5.0 out of 5 stars
138 reviews
23 repeat clients
10 years of experience
Newark, DE, 19711

The most amazing experience with Elisa!! She was incredibly awesome with our very shy 2 dogs. She was extremely patient to gain their trust (not easy to do BTW lol) to the point that they even slept with her after getting to know her- that is how good she is! We loved Elisa and definitely will be our -go to- from now on every time we need a doggy sitter. Our girls got a new bestie with Elisa!

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Kimberly J.
Sitter Profile Image: Faith G.
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Faith G.
from
$75
per night
5.0 out of 5 stars
5 reviews
4 repeat clients
10 years of experience
Oxford, PA, 19363

What a delight it was to have faith watch our four year-old golden retriever! It put me at ease knowing our Doggo was being well cared for. Faith did a wonderful job with communication starting from a meet and greet all the way to letting us know when she was leaving. She went above and beyond with check-ins and photos to washing and remaking the bedbefore she left. We will definitely be using Faith again for our future trips.

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Chase M.
Sitter Profile Image: Destiny P.
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Destiny P.
Star Sitter
from
$65
per night
5.0 out of 5 stars
110 reviews
22 repeat clients
10 years of experience
Bear, DE, 19701

Destiny was great. Daily updates on the pups and she left the house just as she found it. We plan to book her again when needed. Highly recommend!

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Erin K.
Sitter Profile Image: Ashley D.
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Ashley D.
from
$45
per night
5.0 out of 5 stars
6 reviews
15 years of experience
Elkton, MD, 21921

About: I’ve been caring for pets for most of my life, helping friends, family, and neighbors with walking, feeding, bathing, and providing companionship. I’m very attentive, patient, and gentle, and I treat every pet like they’re my own. My goal is always to make pets feel safe, comfortable, and loved while giving owners peace of mind. I work full time on campus, which gives me a consistent schedule along with flexibility during lunch breaks and in the evenings. This allows me to provide reliable care, check-ins, walks, and quality time with pets. I’m also available on weekends and communicate clearly to coordinate schedules that work best for you and your pet. Your pet’s safety, comfort, and routine are always my top priorities. I’m attentive, calm, and reliable, and I make sure pets are well cared for during visits, walks, and evenings. I respect your home, follow instructions closely, and communicate regularly so you feel confident your pet is in safe hands.

Sitter Profile Image: Natalia E.
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Natalia E.
from
$38
per night
7 years of experience
Elkton, MD, 21921

About: Ive taken care of many animals my whole life ive owned a few dogs one of which was born deaf and i had one who went blind at an early age so i know how to handle special need dogs and other pets and have been dog-sitting and cat-sitting for many people since I was 12, I love all animals and will take care of them as if they were my own. I am experienced with young puppies and senior dogs. I am also experienced with dogs that suffer from separation anxiety. I am also very good at sending lots of pictures and daily updates of your fur babies! I am currently working part time at a med spa and I make my own schedule so I will have plenty of flexible time in my day to spend with your pets for whenever you need. I have 2 dogs of my own at home although I do not offer other pets to stay at my home due to having a sensitive senior dog of my own who was born deaf and is now partially blind. I will however be able to stay at your home with your fur babies and even do overnight and extended visits for however long you will need them to be watched. I also will clean up any mess your pets will make because I know how chaotic it may be so please leave out any cleaning supplies I may need.

Sitter Profile Image: Dylan B.
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Dylan B.
from
$65
per night
5.0 out of 5 stars
5 reviews
1 repeat client
12 years of experience
Rising Sun, MD, 21911

Dylan with the help of Sophie were so great with our dogs while we were away! They were exhausted when we got home so we know they played hard. We appreciate their help and the excellent care they provided for our boys.

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Janet K.
Sitter Profile Image: Theodore G.
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Theodore G.
from
$50
per night
10 years of experience
Newark, DE, 19711

About: I’ve been raised around dogs my entire life. My family has had all kinds of dogs; big and small, old and young, energetic and couch potatoes. Friends and family alike call me a dog whisperer for the connections I’m able to make with them. I’m currently finishing my Bachelors of Accounting completely online, so my schedule is completely flexible around your pets needs!! I’m excited to provide the best care possible for your pet!! I’m comfortable walking dogs, crating dogs, feeding dogs, checking all essential needs before leaving them alone, and making sure they are let out plenty of times.

Sitter Profile Image: Sally W.
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Sally W.
from
$32
per night
8 years of experience
Elkton, MD, 21921

About: I’ve always loved caring for animals and have experience with a variety of pets! I regularly dog sit and provide dog walks, and I also have experience horse sitting. I’ve cared for smaller animals as well, including having a pet hedgehog of my own. I’m comfortable following specific routines, giving pets plenty of attention, and making sure they feel safe, happy, and cared for while you’re away! I’m currently a full-time college student, so my schedule varies by day. On school days, I’ll typically be away from home for about 6–8 hours at a time. I’m available around my class schedule for walks, drop-ins, and pet sitting, and I have more flexibility on days when I don’t have classes. I’m happy to work with your pet’s routine and find a schedule that works best for both of us! I care for every pet as if they were my own! I make sure they have fresh food and water, plenty of exercise and playtime, and lots of attention and affection. I’m happy to follow your pet’s normal routine, including walks, feeding schedules, medication if needed, and any special instructions. I also make sure pets are safe, comfortable, and never left without the care they need. I’ll keep you updated with pictures and messages so you can have peace of mind while you’re away!

Sitter Profile Image: Terry C.
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Terry C.
Star Sitter
from
$75
per night
5.0 out of 5 stars
77 reviews
25 repeat clients
15 years of experience
New Castle, DE, 19720

Terry is simply the best. If we could rate 6 stars, we would. She spent a tremendous amount of quality time with Izzy. This was our first long trip away from Izzy our dog in quite a while, but Terry relieved our anxiety with daily updates, videos etc. She is a great communicator. Terry is incredibly thoughtful and an amazing dog sitter who bonded with Izzy. She also took great care of our house which was immaculate with an extra special touch upon our return. Terry was amazing, and we and Izzy look forward to her next visit.

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Mark And Carla S.
Sitter Profile Image: Janelle C.
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Janelle C.
from
$40
per night
5.0 out of 5 stars
3 reviews
1 repeat client
5 years of experience
Newark, DE, 19711

Ellie did a great job caring for my cats. She graciously took my booking very last minute and was flexible and accommodating. My cats loved her!

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Tori S.
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The median cost per night for house sitting in Winding Brook Village is $60

Pet parents share their Rover experiences - Winding Brook Village

1 / 1
5.0 out of 5 stars

Camryn was so helpful and absolutely wonderful! She was diligent in caring for our two dogs while we were away. She did a great job communicating throughout the stay and always provided thoughtful, specific updates. We really appreciated knowing our dogs were well taken care of while we were away!

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Caitlin B.
House Sitting
5.0 out of 5 stars

Ellie did a great job caring for my cats. She graciously took my booking very last minute and was flexible and accommodating. My cats loved her!

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Tori S.
House Sitting
5.0 out of 5 stars

Whitney is wonderful! Her excellent communication, punctuality and competence along with her friendly and kind personality provided me with complete peace of mind to leave my animals for a work conference. My dog and cats loved her; highly recommend!

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Andrea A.
House Sitting
5.0 out of 5 stars

Charlotte was great and our pets were well taken care of during our family trip out of town. Would book again.

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Anthony T.
House Sitting
5.0 out of 5 stars

Jennifer was wonderful. Received pictures everyday along with a note about how the pups were doing. The house was immaculate when I returned. Jennifer will be my go to pet sitter whenever I need to travel without the dogs. Five stars plus for Jennifer💕

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Patricia W.
House Sitting
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Meet local sitters who will treat your pets like family

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Popular requests for house sitting - Winding Brook Village

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Sitters in Winding Brook Village average 4
repeat house sitting clients

FAQs for House Sitting - Winding Brook Village

Frequently asked questions about Rover

The average cost for House Sitting in Winding Brook Village on Rover is $19.26 per night (as of September 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 September 2026, there are 1,285 sitters on Rover offering House Sitting across Winding Brook Village. 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 Winding Brook Village 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 Winding Brook Village 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 Winding Brook Village 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 Winding Brook Village. On Rover:

  • 97% of sitters can help with special care needs
  • 95% can help with giving oral medications or injections
  • 92% 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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