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
214 reviews
60 repeat clients
10 years of experience
Chester, VA, 23831

Allison was great and extremely professional. She took as good of care of our doggos as we do! She gave great updates daily with pics! 10/10 would recommend and will be using her again.

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Josh S.
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 will make your fur babies fill so comfortable! Our Zoey had surgery and she stepped up and took care of her like she was her own. Thank you so much Jessica 🫶🐾💗

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Angela C.
Sitter Profile Image: sabrina s.
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sabrina s.
Star Sitter
from
$65
per night
5.0 out of 5 stars
50 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: Meghan T.
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Meghan T.
from
$60
per night
5.0 out of 5 stars
15 reviews
4 repeat clients
20 years of experience
Chester, VA, 23831

Meghan was such a pleasure to work with. She gave our senior dog the time and attention he deserved and brought out his playful inner puppy. She was great at communicating and we will definitely rebook with her soon!

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Megan A.
Sitter Profile Image: Sarah I.
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Sarah I.
from
$35
per night
5.0 out of 5 stars
8 reviews
1 repeat client
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: Rebecca R.
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Rebecca R.
from
$50
per night
5.0 out of 5 stars
4 reviews
1 repeat client
4 years of experience
Chester, VA, 23831

Rebecca was an absolutely wonderful sitter for our pups! She was incredibly attentive, made sure all of their needs were met, and gave them so much love and care. Our dogs can be a bit high-energy and challenging at times, but she handled them with ease and confidence. From brushing them to bringing them toys and treats, Rebecca went above and beyond to make sure they felt happy, comfortable, and loved while we were away. It was clear that she genuinely cared for them and treated them like her own. We couldn’t have asked for a better sitter and would highly recommend her to anyone looking for exceptional pet care!

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Mackenzie E.
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

Oli was wonderful with our two girls (10yo, 2yo) while we were away for a full week. She gave them lots of attention and kept us really well informed each day while we were gone. She was thoughtful, kind, and quick to address any potential issues or concerns. Our pups were safe, happy, and well fed when we returned. What more can you ask for? We highly recommend Oli as a dog sitter for your next trip!

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Maria T.
Sitter Profile Image: Hana J.
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Hana J.
Star Sitter
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: 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: 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

Jennifer was awesome! She took excellent care of our two dogs, Kona and Milo, while we were out of town. She was very friendly and sent frequent updates letting us know how the dogs were doing. We highly recommend her!

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Katie 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
31 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: Crystal A.
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Crystal A.
from
$63
per night
5.0 out of 5 stars
11 reviews
10 years of experience
Chester, VA, 23831

"I cannot recommend Crystal enough! She took wonderful care of our dog Rigby and our home while we were away — the house was spotless when we got back. Crystal provided regular updates, photos, and even videos so we never had to worry. Our flight got in late and she happily stayed later to make sure Rigby was taken care of. She's responsive, kind, and clearly loves what she does. We'll definitely be booking her again!

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Chris M.
Sitter Profile Image: Emily W.
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Emily W.
from
$30
per night
5.0 out of 5 stars
93 reviews
26 repeat clients
1 year of experience
Colonial Heights, VA, 23834

Emily stayed with our girls for 17 days. She was wonderful. She sent me pictures everyday and told me how they were doing. I was so nervous leaving them for so long. They were probably confused but they definitely enjoyed Emily’s care. She was so sweet with them. It made our trip a pleasure knowing they were in very good hands. Thank you so much Emily. From the bottom of my heart 🧡💜

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Rose Anna H.
Sitter Profile Image: Joseph W.
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Joseph W.
Star Sitter
from
$40
per night
5.0 out of 5 stars
11 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: Emma B.
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Emma B.
from
$50
per night
4.8 out of 5 stars
9 reviews
2 repeat clients
12 years of experience
Petersburg, VA, 23806

Emma was amazing with our home and our pups!! At first I told her she didn’t need to sleep here but with bad weather coming she was more than willing to do so. She came beforehand for a meet and greet to get to know our 4 dogs and asked really good questions. She was very responsive, sent pictures of the dogs throughout her stay, and was very respectful of our home. I highly recommend her and will definitely use her again!!

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Lora S.
Sitter Profile Image: Hailee C.
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Hailee C.
from
$45
per night
4.8 out of 5 stars
32 reviews
11 repeat clients
10 years of experience
Fort Lee, VA, 23801

About: I have taken care of dogs since I was 13 by walking, bathing, feeding, and playing with them. I count my real experience though from owning my own dogs. I trained them from puppies and had them trained with a real dog trainer. I have cared for dogs of all ages from puppies to seniors. I'm currently working part time from home so I'm looking to pick up any job in my free time. Some weeks I have more free time than others and I get my schedule in advance so I can plan ahead or even pick up last minute tasks if need be. I have a fenced in yard and fur babies of my own. I can crate my dogs though if you're not comfortable with your dog being around my dogs. If the service is in your home I can follow the directions you give me to care for them and I will treat them as if they are my own.

Sitter Profile Image: Anslee P.
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Anslee P.
from
$60
per night
4.9 out of 5 stars
56 reviews
17 repeat clients
15 years of experience
Chester, VA, 23831

Anslee was available and communicated with us she is the best, we will continue to have her sit our dogs

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Darcel D.
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
145 reviews
30 repeat clients
15 years of experience
Petersburg, VA, 23803

Kayce did an incredible job with my puppy, who needs consistent care and love! She made sure to send me photos and pupdates all throughout the day, making my day trip extremely easygoing. I felt as if I was leaving my pup with a friend that I could trust! I’m so glad I picked Kayce, and when the time comes, I will request her again! Thank you for everything! You're so awesome!

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Ryan W.
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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

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

Allison is amazing! She works with you even when your schedule changes, she never leaves the pups too long, she gives daily recaps and sends pics at the end of the day, and I swear she leaves our house cleaner than when she arrives! Truly an amazing dogsitter.

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Josh S.
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
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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
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

  • Cashless payments

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  • 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

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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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