House Sitting Windsor Hills

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

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Over 63
pet parents in Windsor Hills have booked house sitting

Windsor Hills, 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: Allison B.
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Allison B.
Star Sitter
from
$32
per night
5.0 out of 5 stars
• 219 reviews
62 repeat clients
10 years of experience
Chester, VA, 23831

“It was a pleasure having Allison watch our pups! She took great care of our senior dog who has various different needs to be taken care of throughout the day.”

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Tori B.
Sitter Profile Image: Arjun W.
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Arjun W.
from
$25
per night
5.0 out of 5 stars
• 2 reviews
2 years of experience
Petersburg, VA, 23806

About: I’ve been helping neighbors and friends with their dogs for the past two years, including walking, feeding, and basic care. I’m great with playful dogs, shy dogs, and puppies who need a little extra patience. I treat every dog like my own and make sure they feel safe and happy. I have a very flexible schedule, especially in the mornings and evenings. Since I’m a college student on break with plenty of free time, I’m able to fit walks, drop-ins, and check-ins around my classes with no problem. Safety is my top priority. Whether I’m caring for a pet in my home or my client’s home, I always follow the owner’s instructions closely. I make sure doors and gates stay secure, walks are controlled, and pets are never left unattended. I keep a calm, clean environment and always give regular updates so owners know their pet is safe.

Sitter Profile Image: Hana J.
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Hana J.
from
$75
per night
5.0 out of 5 stars
• 18 reviews
5 repeat clients
17 years of experience
Colonial Heights, VA, 23834

“Hana was very pleasant, caring and did everything well. She was able to work with my old and difficult dog and give him his insulin injection too. Life saver in a time we really needed her sevices.”

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Iris B.
Sitter Profile Image: Monique & Daniel V.
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Monique & Daniel V.
from
$50
per night
5.0 out of 5 stars
• 55 reviews
23 repeat clients
18 years of experience
Petersburg, VA, 23803

“Did a great job, kept us in loop of anything going on and e how our fur babies were doing. Kept place clean and was there when she said she would be”

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Franklin L.
Sitter Profile Image: Tyeir D.
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Tyeir D.
from
$35
per night
5.0 out of 5 stars
• 3 reviews
1 repeat client
20 years of experience
Chester, VA, 23836

About: I’ve been around animals my entire life. My oldest fur baby (cat) will be turning 20 this year. I also have two small dogs that are 15 and 11 years old. I love animals. I’m currently a full time student. So I can come and love on your fur babies for you while you are away on a trip or at work. Pets are welcomed in my home and are treated with respect. All animals deserve love and attention. I can love on them for you while you are at work or on a trip.

Sitter Profile Image: Maryurith M.
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Maryurith M.
from
$35
per night
5 years of experience
Chester, VA, 23831

About: I’ve raised four German shepherds since they were nine weeks old and I will love and take care of your babies as I did mine! I’m currently working a full time job from Mon-Thurs from 7:30AM to 5:00PM. I have a routine of waking up before 4AM so I have plenty of time in the mornings, I am able to leave work between 11:30AM-1:00PM if I need to check on any pups at home or for potty breaks. I am off during the weekends, I don’t do much on my time off just read, clean and I try to exercise in my apartment. I live in an apartment and I will love to take walks and take your fur babies out when needed and for play time as well. I don’t have any pets at home. I will follow any instructions that you give me to sit your fur babies in my own home or yours.

Sitter Profile Image: Michelle C.
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Michelle C.
from
$60
per night
5.0 out of 5 stars
• 16 reviews
2 repeat clients
10 years of experience
Midlothian, VA, 23832

“Michelle was great to work with! She was very communicative, sent lots of pictures, and took amazing care of the house. We came home to two very happy and well cared for doggies :)”

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Katie O.
Sitter Profile Image: Isaiah M.
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Isaiah M.
from
$55
per night
5.0 out of 5 stars
• 6 reviews
1 repeat client
5 years of experience
Chester, VA, 23836

“We are so grateful for Isaiah! We had to leave town last minute, and he worked with us every step of the way. He came by beforehand to meet our dogs and has a lot of experience. One of our dogs is a new adoption, and she really only likes me, but he was able to get her to a place where she was comfortable and not stressed around him. That alone says a lot about how good he is. He was accommodating to whatever we needed during the sit and was respectful of our home. When we got back, our pets were happy, relaxed, and acting completely like themselves. We’ve had experiences in the past where you could immediately tell the level of care they received, and this was the opposite. It truly felt like they had been cared for the way we would care for them. Isaiah was that person. We will definitely be reaching out to him again in the future.”

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Brienia B.
Sitter Profile Image: Rebecca B.
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Rebecca B.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 48 reviews
20 repeat clients
20 years of experience
Chesterfield, VA, 23234

“Rebecca is a fantastic sitter! She feed and walked Molly early each morning and played with her throughout the day. Molly got so much love and attention while we were away for the holidays and definitely loved Rebecca.”

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Alysha C.
Sitter Profile Image: Oli L.
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Oli L.
Star Sitter
from
$85
per night
5.0 out of 5 stars
• 115 reviews
36 repeat clients
18 years of experience
Richmond, VA, 23231

“Oli was an exceedingly professional sitter. The house was so well maintained on our return. I have a dog with some behavioral quirks and is often very distrusting with new folks at first. She was patient with him and let him warm up at his own pace. She sent daily updates to ease my mind on how everyone was doing. Have no hesitation in booking her.”

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Dawn B.
Sitter Profile Image: Stephenie S.
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Stephenie S.
from
$63
per night
5.0 out of 5 stars
• 3 reviews
30 years of experience
Chesterfield, VA, 23832

“Stephenie stayed with our dogs at our house over the weekend, and she was phenomenal! We received lots of updates and happy pictures of the dogs while we were gone that helped put us at ease knowing the dogs were being well taken care of. Stephanie also maintained their routine and gave them their daily medicines. We are so happy to have met Stephenie and will be booking with her again!”

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Alex B.
Sitter Profile Image: Jamie R.
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Jamie R.
from
$30
per night
5.0 out of 5 stars
• 2 reviews
20 years of experience
Chester, VA, 23831

About: I've had dogs and cats all my life. From pound puppies to pure bred, from puppy to 17+ years old and everything in between. Currently I have 2 Great Danes, a 1 year old female named Willow and a 2 year old male named Otis, and my oldest pound puppy a 17 year old girl named Spazzy. There are also 3 cats in the house. I've had multiple dogs trained and I'm currently working towards a dog training degree myself. I am able to administrator medication and do minor grooming. I have been around animals my entire life and nothing makes me happier than an animal. I am currently a stay at home mom. I have a 14 year old daughter who also adores all animals. I like taking my pups for walks whenever weather permits and when it's icky out we stay inside and play or snuggle up on the couch. Regardless of whatever fun activity we do we do it together and I'm available 24/7 to ensure your pet gets the same level of love, affection, and care as my own. I do not have a fenced yard and although I am located out in the country with a large area to run people do speed past the house so leashes will be used unless otherwise requested. My dogs are fed on a twice daily schedule and I can maintain that or feed on whatever schedule you currently work on with your pet. I am also able to administrator medication to your pet and provide minor grooming if need be. Whatever you and your pets need I'll do my absolute best to provide in a safe and loving environment.

Sitter Profile Image: Jeanleshea E.
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Jeanleshea E.
from
$55
per night
10 years of experience
Chesterfield, VA, 23832

About: I've owned a dog for some years. I watched other people's dogs from puppies to older dogs. I plan on treating your animals with care. I'm currently working a full-time job. But I most certainly have time in the evening and the weekend to dedicate to the care and well-being of your pet. I'd provide meals, restroom breaks, walks and playtime throwing of the ball, games, play dates or care for pet. Companionship while the owner is away.

Sitter Profile Image: Kristen O.
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Kristen O.
from
$44
per night
5.0 out of 5 stars
• 8 reviews
30 years of experience
Chippenham Forest, Richmond, VA, 23225

“Kristen was wonderful! She took excellent care of Pepper and Merlin while we were away. She was attentive to their routines, followed all medication instructions, and made sure they received plenty of attention and quality time. Communication was great throughout, and she kept me informed, which gave me peace of mind knowing they were in good hands. She even went above and beyond by bringing in packages that arrived while we were away. Most importantly, I came home to two happy pups! I would absolutely book with Kristen again and highly recommend her!”

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Alicia D.
Sitter Profile Image: Airlea e.
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Airlea e.
from
$85
per night
5.0 out of 5 stars
• 5 reviews
13 years of experience
Richmond, VA, 23237

About: I have over a decade of professional pet care experience as well as a lifetime of personal pet care experience. I prefer to work with the elderly or medically complex pets as I know they need special attention, adherence to routines, and a calm environment. I focus on providing fun daycare and boarding for pets that don’t do well in regular boarding facilities and require a more home-like experience. Prices are negotiable after a meet and greet. Please fill out your profile in full before meeting! Incomplete/no profile image profiles will not be given my address. I work from home so I spend a majority of my day with my pets and guest pets. Dogs are given mostly free range inside and allowed outside into the huge fenced yard many times a day. They get playtime with other pets and alone time when needed. Our yard is fenced and our house is doggy proofed to avoid trash cans, toilets, and non-chewable items from being accessed. Dogs are crated when they can’t be supervised.

Sitter Profile Image: Allison F.
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Allison F.
from
$35
per night
5.0 out of 5 stars
• 4 reviews
1 repeat client
20 years of experience
Northern Barton Heights, Richmond, VA, 23222

“Allison is a terrific person to take care of a house and pets. Good communication, willing to bend as needed. She pet-sat during the single month when my long-haired dog sheds constantly. We have to be vigilant with cleaning the house to keep up with it. She left the house super clean. I felt like a real adult was taking my place. She's not the type who will accept a job, then change her mind and leave you stranded. She's responsible, a person who could manage any situation as well as could be expected, and is up for what comes her way. Allison kept up with our flight arrivals and offered to stay an extra night if we experienced cancelations. She visited first and I showed her the routine which is just so helpful. All good!”

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Beth M.
Sitter Profile Image: Anna A.
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Anna A.
from
$80
per night
5.0 out of 5 stars
• 11 reviews
1 repeat client
20 years of experience
Hopewell, VA, 23860

“Anna took such amazing care of Cole while I was at work. She kept me updated with how Cole’s day was going and at the end of the day I had a very happy dog. I really appreciate the great care Anna provided!”

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Chelsea B.
Sitter Profile Image: Danielle S.
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Danielle S.
from
$28
per night
10 years of experience
Richmond, VA, 23223

About: As the owner of high energy pets, I am an expert at walks and enrichment. I love animals and am often the first person my friends and family ask to watch their pets when they go out of town. I have a flexible schedule and can be available to care for your pets! On weekends, I am available for petting sitting or long walkies. I have a fenced yard and a neighborhood that is good for walks. I have two pets of my own, a service dog dropout and a cat that likes dogs more than people. I am also willing to drive to your home to care for your pets.

Sitter Profile Image: Ashley Z.
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Ashley Z.
from
$60
per night
8 years of experience
Colonial Heights, VA, 23834

About: I have been pet sitting both on and off rover for 7 years. I was in the veterinary field for 6 before switching over to my current profession. I love all animals big and small and can’t wait to watch and care for your babies! 🐶🐱 I do work full time Monday-Friday 8-5 but will make sure your animals are taken care of before work and immediately after! If the location is near my job I can also go over there for a lunch walk or play. I do offer both staying and checking in a few times a day. I will typically have some errands to run here and there but for the most part I will be at your home hanging out with your pets and sending you all the pictures!

Sitter Profile Image: Reese V.
Verified Enhanced Background Check
Reese V.
from
$28
per night
5 years of experience
Dinwiddie, VA, 23841

About: I have been taken care of pets for 5 years. My family’s, friends, community, and others. I am always willing to spend time with pets and care for them! I’m currently a high school student who has sports which i attend during after school hours. However, during the summer i am free to spend time with furry friends! I can feed, water, play, medicate, and provide anything for your animals. I can crate them as needed and I will keep the house clean after my visit.

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

Pet parents share their Rover experiences - Windsor Hills

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5.0 out of 5 stars

Allison took wonderful care of my boys! She was attentive to their needs and sent me regular updates to put my mind at ease.

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Colleen K.
House Sitting
5.0 out of 5 stars

Just Great! Lots of upbeat enthusiasm when meeting us and our dog. Good communication while we were away detailing feeding and walks, complete with pictures. Our home was in good order upon our return.

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Bob M.
House Sitting
5.0 out of 5 stars

Hana was very pleasant, caring and did everything well. She was able to work with my old and difficult dog and give him his insulin injection too. Life saver in a time we really needed her sevices.

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Iris B.
House Sitting
5.0 out of 5 stars

Jessica is great and Grey enjoyed her company. She also went the extra mile for my last minute planning and watered my garden. We will use her services again!

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amy a.
House Sitting
5.0 out of 5 stars

Cassidy is the best! She took care of our girls like her own, and was more than willing to help with an impromptu vet visit when it looked like one of our dogs had a UTI (she didn’t she was just being a weirdo). We will definitely be reaching out to her again. The communication and picture taking are a 12/10. :)

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Alyssa J.
House Sitting
5.0 out of 5 stars

Mia was absolutely INCREDIBLE!!!!! She would constantly send picture updates and made me feel secure as a nervous dog mommy. I will definitely hire her again and will recommend her to anyone needing a petsitter.

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Abigail P.
House Sitting
5.0 out of 5 stars

Fantastic house/pet sitter for our cats, dog and chickens! Brenda was so friendly and communicative - we've had some bad pet sitters in the past but Brenda was great from beginning to end and we felt safe with our fur babies in her care! Highly recommend - will use her again!

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Jennifer C.
House Sitting
5.0 out of 5 stars

Linda did a fabulous job taking care of my two dogs, one of whom can be a bit tricky with people he doesn't know. From the start, I appreciated Linda's professional yet laid-back manner. Communication remained top-notch before and during our trip. It was so nice being able to relax knowing our dogs were in great hands. We absolutely hope to use Linda again!

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Jenna D.
House Sitting
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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
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How to book house sitting

  1. 1. Search

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Popular requests for house sitting - Windsor Hills

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Sitters in Windsor Hills average 4
repeat house sitting clients

FAQs for House Sitting - Windsor Hills

Frequently asked questions about Rover

The average cost of House Sitting in Windsor Hills is $39 per night as of October 2026. Most bookings cost between $30 and $78 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 1,501 sitters on Rover offering House Sitting across Windsor Hills. 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 Windsor Hills 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 Windsor Hills 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 Windsor Hills 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 Windsor Hills. On Rover:

  • 90% 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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