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: Elizabeth M.
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Elizabeth M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 242 reviews
83 repeat clients
15 years of experience
Henrico, VA, 23238

“Elizabeth stayed at the house for one night and took really great care of our Yorkie, Belle. She kept me updated and sent a couple of photos. I would definitely book with Elizabeth again.😊”

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Kay S.
Sitter Profile Image: Riley O.
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Riley O.
Star Sitter
from
$55
per night
4.9 out of 5 stars
• 94 reviews
47 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: Tiffany C.
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Tiffany C.
from
$25
per night
4.9 out of 5 stars
• 66 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: Emily A.
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Emily A.
Star Sitter
from
$70
per night
5.0 out of 5 stars
• 55 reviews
17 repeat clients
15 years of experience
Henrico, VA, 23238

“Emily already has great reviews and this will be another to add! She was professional, kind, communicated easily and left us feeling comfortable that our two pups were in good hands which left us to enjoy our mini vacation. Our home was clean and respected and pups well loved and taken care of. We could not speak more highly of Emily and hope to use her again! Do not hesitate to reach out to Emily!”

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Amanda and Jason R.
Sitter Profile Image: Timothy M.
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Timothy M.
from
$45
per night
5.0 out of 5 stars
• 3 reviews
5 years of experience
Manakin-Sabot, VA, 23103

“Timothy was great! He asked all of the right questions leading up to watching my dog and cat and kept in touch during the stay. I was very happy and so were my pets!”

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Denise T.
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: Janini C.
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Janini C.
from
$65
per night
5.0 out of 5 stars
• 21 reviews
7 repeat clients
8 years of experience
Richmond, VA, 23236

“Janini did a fantastic job house sitting for our puppy while we were on vacation. Her communication was excellent and felt we were in good hands the whole time. She was great with sending updates, pictures and videos which gave us peace of mind. Highly recommend her to watch your furry friends.”

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Zach R.
Sitter Profile Image: Nazneen A.
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Nazneen A.
from
$45
per night
5.0 out of 5 stars
• 21 reviews
13 repeat clients
6 years of experience
Richmond, VA, 23059

“She was amazing :)”

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Jeordy M.
Sitter Profile Image: Carolyn H.
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Carolyn H.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 19 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: Madelaine E.
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Madelaine E.
from
$65
per night
5.0 out of 5 stars
• 87 reviews
45 repeat clients
50 years of experience
Eastland Park-Dixie Plantation, Richmond, VA, 23230

“Madelaine was a wonderful house and dog sitter! Highly recommend her! Totally professional and trustworthy- and our dogs miss her already-srsly, they wanted in the guest room to find her the next day! Ha!”

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Patty O.
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: Collette J.
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Collette J.
from
$40
per night
4.8 out of 5 stars
• 32 reviews
8 repeat clients
25 years of experience
Richmond, VA, 23228

“Collette was a dream sitter. Stayed full time with my senior pups and my house was exactly as it was when I left. No dishes in the sink, no mess. If anything, they are exhausted from being spoiled to pieces. It’s hard to find a sitter who won’t leave the pups alone for hours on end…if you’re looking for someone who truly cares, book Collette!”

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Ashley D.
Sitter Profile Image: Helena B.
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Helena B.
Star Sitter
from
$80
per night
5.0 out of 5 stars
• 32 reviews
11 repeat clients
10 years of experience
Henrico, VA, 23294

“Lena was great! She sent updates with many pictures of Bosun and Ferry carrying on happily without us! She messaged us with questions as well, which we appreciated because it showed she cared about making sure things carried on as they would if we were home. We are booking her help again!”

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Madison S.
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: 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: Vanessa K.
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Vanessa K.
from
$65
per night
5.0 out of 5 stars
• 6 reviews
26 years of experience
Glen Allen, VA, 23060

“Vanessa took great care of our four pets! She stuck exactly to their usual schedule, even though that meant waking up very early every morning to feed them breakfast. She was communicative and provided regular updates. Vanessa took good care of the house too, leaving it as tidy as she found it. Would definitely book with her again!”

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Sydney M.
Sitter Profile Image: Sabrina F.
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Sabrina F.
from
$45
per night
5.0 out of 5 stars
• 7 reviews
2 repeat clients
6 years of experience
Richmond, VA, 23226

“Great with our dogs over a long weekend and left the house spotless. Reliable, concerned and communicative. Our boys were well taken care of.”

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John P.
Sitter Profile Image: Victor S.
Verified Enhanced Background Check
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

“This was the first time V dogsat for us and it was a wonderful experience! V was easy to communicate with, took excellent care of our pup, and even went above and beyond on caring for our home. Highly recommend!!”

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Jordan B.
Sitter Profile Image: Kristen O.
Verified Enhanced Background Check
Kristen O.
from
$39
per night
5.0 out of 5 stars
• 6 reviews
30 years of experience
Chippenham Forest, Richmond, VA, 23225

“Very friendly and communicative. Kept us updated throughout the stay. Would recommend Kristen to look after your dog or cat!”

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Lianna S.
Sitter Profile Image: Kelly & Greg L.
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Kelly & Greg L.
from
$40
per night
20 years of experience
Glen Allen, VA, 23059

About: As a Registered Nurse, caring for others has always been at the heart of who I am. That same compassion and attention to detail naturally extends to animals.. I know your pets are family, and I’ll care for them with the same patience, love, and vigilance I’d want for my own. Whether it’s keeping them on their routine, giving medications, or simply providing plenty of playtime, cuddles, and companionship, my goal is to keep them safe, healthy, happy, and loved while you’re away so you can have complete peace of mind. I believe your pets deserve my undivided attention. That’s why I only accept one family at a time. My hybrid work schedule allows me to work from home two days per week, and I can often adjust those days to be home even more with your pet. Depending on how far your home is from my office, I am also be able to come home for lunch for walks or playtime. If your pet is happiest in their own environment, I’m happy to provide care in your home. I can care for multiple dogs, cats, or a combination of pets, and I’m also open to caring for other animals. My goal is to keep your pets safe, comfortable, and maintain their normal routine while you’re away. Every pet is unique, so I’d love to learn about your needs and how I can provide the best care for your furry (or feathered or scaled!) family members. Let’s chat and create a plan that’s perfect for you and your pets!

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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

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5.0 out of 5 stars

Riley was great! We ended up stuck on vacation for an extra 4 days and she stayed to watch our dog. Couldn't be happier.

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Nicole W.
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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Find pet care near you

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 October 2026, there are 1,416 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.

<b>Tip:</b> 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 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 Meet & Greet .

sitters on Rover set their own cancellation policy , 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 Windy Run. On Rover:

  • 95% 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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