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.

1 / 1
Sitter Profile Image: Allison B.
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Allison B.
Star Sitter
from
$32
per night
5.0 out of 5 stars
215 reviews
60 repeat clients
10 years of experience
Chester, VA, 23831

Allison did a great job! She was wonderful with making sure all the details were squared away before we left (like double checking about where we'd want her to sleep for staying over and making sure she knew where everything was for them). And, she was good with providing updates! They all looked great when we got home. Thanks!!

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Kateland H.
Sitter Profile Image: sabrina s.
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sabrina s.
Star Sitter
from
$65
per night
5.0 out of 5 stars
54 reviews
14 repeat clients
15 years of experience
Chester, VA, 23831

Sabrina is such a fantastic pet sitter, a true God send! It was the first time we have ever left our boys alone with anyone and she was just fabulous!! She sent so many pictures, and kept us posted the entire time we were gone. She even took care of our lizards and fish for us. So reasonably priced and worth every penny. We will definitely be using her again and again and again!!!

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Christine D.
Sitter Profile Image: Jessica R.
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Jessica R.
from
$60
per night
5.0 out of 5 stars
41 reviews
21 repeat clients
18 years of experience
Chester, VA, 23831

Jessica was so kind and flexible with our needs. She loved our girls so well and took amazing care of them. We received so many photos and videos of our two happy pups it made all the difference. Highly recommend and will be using her again!

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Brielle O.
Sitter Profile Image: Meghan T.
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Meghan T.
from
$60
per night
5.0 out of 5 stars
16 reviews
4 repeat clients
20 years of experience
Chester, VA, 23831

It was not easy leaving my dogs but I knew they were in good hands the minute I met Meghan. She took great care of my dogs and sent me detailed updates. I highly recommend Meghan and will definitely use her again!

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Kourtney D.
Sitter Profile Image: Sarah I.
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Sarah I.
from
$35
per night
5.0 out of 5 stars
8 reviews
2 repeat clients
7 years of experience
Chesterfield, VA, 23832

Sarah has house sit/dog sit for us twice now and is absolutely amazing! She keeps us updated, sends pics, and makes sure the house is just as clean as we left it! Plus our fur babies loooovvveee her! We highly recommend hiring her! Thanks again Sarah!!!!

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

Grateful for Hana’s continued service. She has a real rapport with my pup and is very kind and thoughtful with him. But also knows how to lovingly discipline him. Thanks!

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Anthony G.
Sitter Profile Image: Oli L.
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Oli L.
Star Sitter
from
$85
per night
5.0 out of 5 stars
109 reviews
35 repeat clients
18 years of experience
Hopewell, VA, 23860

We have found our forever pet sitter! Oli was there for my husband and I as we welcomed our son into this world (a week early!) and the comfort she provided by taking such diligent care of our pets was invaluable. Oli is kind, organized and genuinely loving towards animals.

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Emma H.
Sitter Profile Image: Jennifer Z.
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Jennifer Z.
from
$40
per night
5.0 out of 5 stars
13 reviews
5 repeat clients
8 years of experience
North Chesterfield, VA, 23234

Jenni was a great choice to watch our fur baby overnight because of a last minute trip my partner & I had to take for a funeral. Due to our unexpected time constraint beforehand, she came over the same day of the booking and met our dog Hank & learned his routine. While we were away, she sent lots of pictures & gave us updates every so often so we were always in the know. We would definitely have Jenni watch Hank again in the future and highly recommend her for the pet sitting needs of other folks too!

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Peter C.
Sitter Profile Image: Crystal A.
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Crystal A.
from
$63
per night
5.0 out of 5 stars
12 reviews
10 years of experience
Chester, VA, 23831

Crystal was AWESOME, and I was so appreciative of her taking my very last minute booking. She was so professional and did such a great job with my dog and my home. I came home to an organization house and a very happy dog. I would definitely hire her again!

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Ada H.
Sitter Profile Image: Monique & Daniel V.
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Monique & Daniel V.
Star Sitter
from
$50
per night
5.0 out of 5 stars
54 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: Samantha B.
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Samantha B.
from
$60
per night
5.0 out of 5 stars
32 reviews
17 repeat clients
30 years of experience
Chester, VA, 23831

Samantha took AMAZING care of our babies and our home. She sent lots of updates and photos giving us peace of mind. Our very shy cat even came out to get cuddles with Samantha. She left our house so clean as well! She made us some special homemade popcorn as a coming home gift. A very thoughtful added touch.we will definitely use Samantha again when we travel.

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Jennifer G.
Sitter Profile Image: Joseph W.
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Joseph W.
Star Sitter
from
$40
per night
5.0 out of 5 stars
12 reviews
3 repeat clients
5 years of experience
Chester, VA, 23836

First time house sitting for our Bernedoodle and she was well handled by Joey. He took well care of her as usual, played, walked her and gave her medicine. 👍

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James K.
Sitter Profile Image: Linda A.
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Linda A.
from
$65
per night
5.0 out of 5 stars
22 reviews
4 repeat clients
30 years of experience
Chester, VA, 23831

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.
Sitter Profile Image: Tyeir D.
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Tyeir D.
from
$30
per night
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: Grace L.
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Grace L.
from
$70
per night
5.0 out of 5 stars
40 reviews
14 repeat clients
17 years of experience
South Chesterfield, VA, 23834

Grace was amazing with our dogs and house. The pups were super happy and she sent us pics of them while we were gone. Her flexibility during her stay took away all our concerns. I would definitely recommend her to others. I will schedule her again. 😃😃😃😃😃😃

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Christina B.
Sitter Profile Image: Kristie C.
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Kristie C.
from
$40
per night
6 years of experience
Chester, VA, 23831

About: I have been taking care of dogs and cats of all kinds since 2017, I have been a dog groomer for 4 years. I am certified in pet CPR. Pet parents have relied on me with peace of mind to, feed, give potty breaks and even bathe/groom their pets! I work full time as a dog groomer, I will be able to take care of your fur baby in 30 minute increments. I am available in the morning 7am-8:30am and in the evening 4:30pm-10pm. I do in customer house pet sitting-drop ins and overnights. Week days I work full time but I will let the dogs out in the morning, after work and In the evening. I can crate them if needed or let them run free whatever works best for you and your family !

Sitter Profile Image: Lashell D.
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Lashell D.
from
$112
per night
5.0 out of 5 stars
32 reviews
6 repeat clients
15 years of experience
Chester, VA, 23831

About: Hello everyone, Put code LASHED02561 in promotion box for an immediate redemption of $20 off your first booking with me. Or use this link https://www.rover.com/sit/lashed02561 I’m an animal whisperer with over 15 years of experience, skilled in creating tailored training techniques for various dog breeds. My compassionate methods prioritize positive reinforcement, ensuring each dog feels understood. My rates reflect the quality of care I provide, including training, evaluations, and ongoing support to strengthen your bond with your pet. As a passionate pet sitter, I also offer dedicated care for dogs, cats, and small critters, customizing my services to meet their unique needs. I take pride in being a trusted name in the pet sitting industry. If you’re seeking a committed pet sitter who loves animals, I would be honored to care for your furry family members. Flexibility and Availability: Working from home and being available seven days a week allows me to accommodate various booking requests. I can offer day care services for a few hours or provide care for extended periods, such as up to two weeks. Same-day bookings can be accepted. As a Professional Pet Care Specialist, I approach each canine companion with equal attention and dedication. I provide personalized care, ensuring that every pup receives the utmost love, care, and adherence to any specific instructions provided by their owners. I recognize and respect the uniqueness of each dog, understanding that their individual needs and preferences may vary. Rest assured that I am committed to delivering exceptional care and creating a nurturing environment for your beloved furry friend. Thank you for entrusting their well-being to me.

Sitter Profile Image: Kayce M.
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Kayce M.
from
$85
per night
4.9 out of 5 stars
149 reviews
30 repeat clients
15 years of experience
Petersburg, VA, 23803

Kayce was an amazing stand in for loving on our pups and kitties. What better than yourself as a pet parent? An amazing lady like Kayce! She was perfect and so accommodating for in home stay to care for our 4 dogs (ages 3 months to 11 years old) and our 2 young cats. She was prompt, courteous and respectful while being so kind and loving to our pets and accommodating our schedule. I’d highly recommend her as well as very likely to use her again for our fur babies. 5 stars all around.

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Theresa L.
Sitter Profile Image: Allyson B.
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Allyson B.
from
$40
per night
4.8 out of 5 stars
58 reviews
17 repeat clients
15 years of experience
Henrico, VA, 23231

Allyson was responsive and always sent pictures and updates while we were away, which put my mind at ease! My dog and cat seemed very happy and calm with her care, and everything with our home was in order / clean upon our return. Would use Allyson again to watch our fur babies!

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Emma W.
Sitter Profile Image: Candice D.
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Candice D.
from
$60
per night
5.0 out of 5 stars
11 reviews
3 repeat clients
25 years of experience
North Chesterfield, VA, 23237

Candice accommodated my reactive Aussie who is very distrusting of new people. She gave her space and let my doggo make all the moves which I really appreciate. She’s been communicative the whole time and sent pictures! I will definitely be using her again now that my dog has built some trust with her.

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Jamie K.
1 / 1
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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

1 / 1
5.0 out of 5 stars

It is always a pleasure to having Allison come and dog sit for us! She is very communicative and sends pictures from her visit. Definitely would recommend her to take care of your babies

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Tori B.
House Sitting
5.0 out of 5 stars

Awesome job with our fuzzy friends as always Emily does a fantastic job connecting and communicating with pic’s throughout

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Jeff J.
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
5.0 out of 5 stars

Brandie took excellent care of our dogs. She went above and beyond and we would definitely book her again!

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Jennifer M.
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

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Popular requests for house sitting - Windsor Hills

Select a filter and find qualifying sitters offering house sitting.

Sitters in Windsor Hills average 4
repeat house sitting clients

FAQs for House Sitting - Windsor Hills

Frequently asked questions about Rover

The average cost for House Sitting in Windsor Hills on Rover is $38.85 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 1,486 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 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 Windsor Hills. On Rover:

  • 94% of sitters can help with special care needs
  • 97% can help with giving oral medications or injections
  • 99% 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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