House Sitting Windy Run

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Windy Run, 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: Emily A.
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Emily A.
Star Sitter
from
$70
per night
5.0 out of 5 stars
53 reviews
16 repeat clients
15 years of experience
Henrico, VA, 23238

Emily truly shines in her role! She is not only kind and professional but also exhibits an extraordinary level of compassion for all my senior pets. Her dedication goes above and beyond, making a meaningful difference in their care.

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Carolina D.
Sitter Profile Image: Carolyn H.
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Carolyn H.
Star Sitter
from
$45
per night
5.0 out of 5 stars
18 reviews
6 repeat clients
5 years of experience
Richmond, VA, 23233

Carolyn is a wonderful pet/house sitter. This is the second time she’s taken care of our pup, and both times she did a great job. She’s very responsible and careful. She left our house clean and orderly. We hope to use her again.

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Becky W.
Sitter Profile Image: McKenzie A.
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McKenzie A.
from
$26
per night
4.8 out of 5 stars
7 reviews
2 repeat clients
10 years of experience
Richmond, VA, 23238

McKenzie is a pro - very responsive, excellent communication and a great caregiver to our Stella - she goes the extra mile to ensure comfort for your pet and takes great care of your home when sitting. Could not recommend her more.

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Michael H.
Sitter Profile Image: Collette J.
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Collette J.
from
$26
per night
4.8 out of 5 stars
32 reviews
8 repeat clients
25 years of experience
Richmond, VA, 23228

Collette did a great job taking care of our two girls. We got multiple daily photos and small updates on how everyone was doing. They also made the girls comfortable and made them felt like we never left. Collette also made sure our house was clean and tidy before we returned. Highly recommend!

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Tyler A.
Sitter Profile Image: Tiffany C.
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Tiffany C.
from
$25
per night
4.9 out of 5 stars
65 reviews
27 repeat clients
8 years of experience
Glen Allen, VA, 23059

I couldn’t be happier with Tiffany! She did an amazing job taking care of our pups while we were away — they were happy, relaxed, and clearly loved all the attention and care she gave them. She kept me updated with photos and messages, which gave me total peace of mind. The house was spotless when we got back, and everything was exactly as we left it. I highly recommend her to anyone looking for someone trustworthy, kind, and attentive with pets!

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Bridget A.
Sitter Profile Image: Helena B.
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Helena B.
Star Sitter
from
$80
per night
5.0 out of 5 stars
31 reviews
10 repeat clients
10 years of experience
Henrico, VA, 23294

Helena was absolutely AMAZING!!! This was our first time using Rover and the first time we left our dog overnight. She sent us pictures and updates throughout the time we were gone, showing just how relaxed and happy our dog was in her care. When he whined about sleeping in his crate, she kindly let him share the bed with her (with our approval, of course!). He even seemed disappointed when we came home 😉. We cannot recommend Helena more highly!!

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Linda M.
Sitter Profile Image: Laura M.
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Laura M.
from
$40
per night
4.8 out of 5 stars
8 reviews
1 repeat client
9 years of experience
Crozier, VA, 23039

Laura was communicative and wonderful! She gave me updates throughout the day and seemed to put great care into making sure my two dogs were comfortable and happy while I was away.

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Jenna R.
Sitter Profile Image: Victor S.
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Victor S.
Star Sitter
from
$70
per night
4.9 out of 5 stars
36 reviews
14 repeat clients
4 years of experience
The Museum District, Richmond, VA, 23220

Victor was an exceptional guest and a wonderful caretaker for my two dogs. He followed all instructions carefully, maintained great communication while I was away, and most importantly, my dogs absolutely adored him. The house was spotless when I returned! Victor went above and beyond to ensure everything was in order, and I felt completely at ease knowing my pets and home were in such capable hands. I would not hesitate to welcome him back again. Highly recommended!

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Cole M.
Sitter Profile Image: Nazneen A.
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Nazneen A.
from
$45
per night
5.0 out of 5 stars
17 reviews
11 repeat clients
6 years of experience
Richmond, VA, 23059

She was amazing :)

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Jeordy M.
Sitter Profile Image: Wesley F.
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Wesley F.
from
$55
per night
5.0 out of 5 stars
21 reviews
8 repeat clients
10 years of experience
Glen Allen, VA, 23060

Wesley was amazing. Kept in contact with us. Took amazing care of our pups. Let us know if any issues. She even got my little old pup to cuddle and that is rare. He really doesn’t like many people! She was amazing and we plan to use her again and again!!

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Mary B.
Sitter Profile Image: Michaela W.
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Michaela W.
from
$28
per night
20 years of experience
Glen Allen, VA, 23059

About: I’ve been surrounded by dogs and cats for as long as I can remember! Growing up as an only child, our pets were my built-in best friends and caring for them was my responsibility from a young age. That love for animals has only grown with me. Over the years, friends and neighbors have trusted me to drop in, walk, and stay with their pets while they’re away, and I genuinely love getting to know each animal and their individual personality, routines, and quirks. These days, I’m a mom to a toddler and three very loved pets of my own, including my Golden Retriever, who is always happy to join me for a random walk during the day! I’d love to add a few more furry friends to my walking schedule and give them the same attention, patience, and affection I give my own. In our house, pets aren’t just pets, they’re family. I know how much trust it takes to leave a beloved pet in someone else’s care, and I’ll always treat yours with the same love and importance I would want someone to give mine. Whether they need a good walk, some playtime, company, or just someone to make sure they feel safe and loved while you’re away, I’d be so happy to be that person! I work from home, which gives me a lot of flexibility throughout my day! I’m able to come and go as needed, so fitting walks, drop-ins, and visits into my daily routine is easy. I also have a great support system at home, which allows me to be flexible with scheduling and give your pets the time and attention they need. Because my work is remote, I can also bring it with me when needed! If your pet would benefit from a little extra company beyond a typical drop-in, I’m happy to settle in with my laptop and spend some additional time with them rather than rushing out the door. As a mom and pet owner myself, caring for both little humans and furry family members is already a big part of my everyday life. My child has been raised around animals and taught from the beginning to be gentle and respectful of their space. My schedule allows me plenty of freedom to make pet care a natural, and very welcome, part of my day! In our house, pet care is part of our everyday routine! I make sure fresh water is always available both upstairs and downstairs and changed daily, my cats’ food is checked and replenished each day, and my dog eats on a consistent twice-daily schedule. When I’m home, my dog gets a morning or afternoon walk, plenty of trips outside to our fenced backyard throughout the day, and usually a daycare day or two each week for some extra exercise and socialization. When I leave the house, I’m also very mindful of his safety, he stays comfortably downstairs with access to his bed and water, potential chewing hazards are put away, and toys that require supervision are never left out. I’d bring that same level of attention to caring for your pets! I know every animal and household has its own routine, so I’m happy to follow your feeding schedule, potty or litter box routine, walking preferences, playtime rules, and any other instructions that help your pet feel comfortable. Whether your pet thrives on a strict schedule or has their own wonderfully specific set of quirks, I want their routine to feel as normal as possible while you’re away.

Sitter Profile Image: Sara W.
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Sara W.
from
$60
per night
5.0 out of 5 stars
5 reviews
1 repeat client
15 years of experience
Henrico, VA, 23229

Sara was very responsible and loving to my great Dane and spent a lot of time with her sent me pictures and kept me posted. I would highly recommend her to sit with your animals.

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Tina B.
Sitter Profile Image: Riley O.
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Riley O.
Star Sitter
from
$55
per night
4.9 out of 5 stars
93 reviews
46 repeat clients
7 years of experience
manakin sabot, VA, 23103

Riley took excellent care of my 3 senior dogs, all 3 on meds, including 1 that is diabetic and needed blood glucose monitoring and insulin shots. I was thrilled to find someone with experience with diabetes. Thanks Riley!

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Emily H.
Sitter Profile Image: Kim A.
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Kim A.
Star Sitter
from
$110
per night
5.0 out of 5 stars
45 reviews
12 repeat clients
45 years of experience
Midlothian, VA, 23113

Kim was awesome! We received a lot of photos throughout our visit and I could tell that she kept our pup entertained and loved while we were gone.

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Hali G.
Sitter Profile Image: Marina S.
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Marina S.
from
$30
per night
5.0 out of 5 stars
3 reviews
10 years of experience
Richmond, VA, 23225

Marina was fantastic highly recommend her great communicator and Butch loved having her watch him

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Babs P.
Sitter Profile Image: Esther H.
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Esther H.
from
$50
per night
5.0 out of 5 stars
4 reviews
2 repeat clients
2 years of experience
Richmond, VA, 23229

Very good dog sitter exceptional person bonded quickly with tater had a great time. Extremely polite and thoroughly loved the puppy and it showed.

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Wayne W.
Sitter Profile Image: Lothrop "Ajax" G.
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Lothrop "Ajax" G.
from
$40
per night
3.8 out of 5 stars
14 reviews
2 repeat clients
30 years of experience
Henrico, VA, 23294

Ajax is terrific--we will definitely use him again. He stayed in our home, and everything was immaculate when we returned and our 2 Shelties were very happy pups!

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Darcy F.
Sitter Profile Image: Emmy A.
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Emmy A.
from
$80
per night
5.0 out of 5 stars
5 reviews
10 years of experience
Manakin-Sabot, VA, 23103

About: I’ve pet sit for neighbors, family and friends since I’ve been able to drive. I have some pets that I have been watching for multiple years. I currently work full time but it is flexible. I can let you dog out before and after work, and potentially during my lunch break if you are nearby! I can easily crate your dog and easily put them on a leash and take them on walks. If you have strict rules with your pet, I will try my hardest to enforce your rules.

Sitter Profile Image: Timothy M.
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Timothy M.
from
$45
per night
5 years of experience
Richmond, VA, 23238

About: I’ve dog-sat for neighbors throughout childhood, often look after my parents’ two dogs while they are away, and volunteer at the Richmond SPCA. Dog/cat for family friends while they were on sabbatical for four months. I have a flexible schedule thanks to my hybrid/remote CPA position. I can often adjust my workday to accommodate pet care, including walks, feedings, playtime, and overnight stays. I typically have evenings and weekends free, allowing me to provide consistent, reliable care and plenty of attention. I have experience caring for both crate-trained and free-roaming pets and always follow each owner’s routines and instructions. I prioritize safety, cleanliness, and making pets feel comfortable in their environment. I enjoy long walks, playtime, and relaxing with a furry companion, ensuring they receive plenty of attention, affection, and exercise while you’re away.

Sitter Profile Image: Alexandra C.
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Alexandra C.
from
$55
per night
5.0 out of 5 stars
4 reviews
12 years of experience
Glen Allen, VA, 23059

Alexandra was amazing!! She treated our fur babies like her own. Just being around her you can tell she genuinely LOVES animals!! We will most definitely be using her services again!!!

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Nicole R.
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The median cost per night for house sitting in Windy Run is $50

Pet parents share their Rover experiences - Windy Run

1 / 1
5.0 out of 5 stars

Riley was great with Bruno. She understands the needs of a senior dog and was very patient with our boy and clearly gave him a lot of love and attention. Bruno was very calm and peaceful upon our return. We would definitely hire her again and recommend her to friends and family.

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Arun Kumar P.
House Sitting
5.0 out of 5 stars

Riley always takes such great care of our pups which is saying something considering we have 3 large babies.

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Leigh J.
House Sitting
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Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

  • Cashless payments

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

  • Reservation protection

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

  • World-class support

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

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

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

Popular requests for house sitting - Windy Run

Select a filter and find qualifying sitters offering house sitting.

Sitters in Windy Run average 4
repeat house sitting clients

FAQs for House Sitting - Windy Run

Frequently asked questions about Rover

As of September 2026, there are 1,408 sitters on Rover offering House Sitting across Windy Run. 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 Windy Run 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 Windy Run 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 Windy Run 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 Windy Run. On Rover:

  • 96% of sitters can help with special care needs
  • 98% can help with giving oral medications or injections
  • 98% 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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