House Sitting In Windsor

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

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Top rated Windsor house sitters

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: Zander M.
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Zander M.
from
$55
per night
5.0 out of 5 stars
25 reviews
6 repeat clients
18 years of experience
Richmond, VA, 23220

Zander was great! He took great care of my two kitties and my house. :)

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Suzanne R.
Sitter Profile Image: Samariah H.
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Samariah H.
from
$50
per night
4 years of experience
Richmond, VA, 23224

About: I have experience caring for dogs through both long-term and everyday responsibilities, including helping raise my aunt’s dog from puppyhood and regularly caring for my boyfriend’s dog. My responsibilities have included walking, feeding, playtime, maintaining routines, and providing companionship to help pets feel safe, comfortable, and cared for while their owners are away. What sets me apart from other sitters is the level of care and attention I give to each pet individually. I understand that being away from their owner can be stressful for some animals, so I focus on creating a calm, reassuring, and positive environment where they feel secure and loved. My experience caring for puppies has also taught me patience, consistency, and the importance of paying close attention to behavior, routines, and energy levels. I treat every pet with the same care, compassion, and responsibility I would want for my own animals. Pet care fits naturally into my daily routine because I already spend a lot of time caring for my own cats. I make sure they’re fed, comfortable, and getting plenty of attention and playtime throughout the day. I even take my cat on walks, so I’m very attentive to both physical activity and emotional enrichment. Caring for animals is something I genuinely enjoy, so being patient, observant, and consistent with their routines comes very naturally to me. II believe pets communicate their needs through their behavior and body language, so I always pay close attention to make sure they feel safe, comfortable, and understood. I respect each pet’s boundaries while also giving them plenty of attention, playtime, and care. In both my home and a client’s home, I focus on keeping pets comfortable, maintaining their routine, and making sure they don’t feel lonely or stressed while their owner is away.

Sitter Profile Image: Sara G.
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Sara G.
from
$60
per night
5.0 out of 5 stars
26 reviews
8 repeat clients
11 years of experience
Richmond, VA, 23220

Sara was great with my dogs. I really appreciated how many photos she sent me while watching them and could see how well my anxious dogs were warming up to her.

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Emily H.
Sitter Profile Image: Alexander S.
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Alexander S.
Star Sitter
from
$40
per night
5.0 out of 5 stars
33 reviews
8 repeat clients
47 years of experience
Old Town Manchester, Richmond, VA, 23224

Alex was amazing - very professional! He was very attentive to our wishes and instructions, excellent communicator, punctual and all the things you would expect from hiring a pro. The house was left clean and he genuinely seems to care for our pets and enjoy their company. Got photos every day and followed our complicated medication schedule. The dogs seemed happy and healthy when we returned! We HIGHLY recommend!

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Sam K.
Sitter Profile Image: Oli L.
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Oli L.
Star Sitter
from
$80
per night
5.0 out of 5 stars
105 reviews
35 repeat clients
18 years of experience
Richmond, VA, 23221

Oli was very communicative, left our house cleaner than we left it, and our pup was so well-taken care of for the two weeks we were gone!! We could very much tell when we got home, and by the funny tidbits Oli sent us that showed how much she was in tune with Maddie! We would definitely use Oli again! And so appreciate how happy Maddie was and how clean everything was upon our arrival! When we came home in between her departing and us getting back, she even had calm music playing for Maddie! Oli is a gem! ❤️

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Amy B.
Sitter Profile Image: Mitchell I.
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Mitchell I.
from
$40
per night
2 years of experience
Richmond, VA, 23224

About: Hi there! I'm Mitchell, an experienced and passionate dog lover excited to take care of your furry friend. Whether your dog enjoys playtime, cuddles, or quiet walks, I provide personalized care to make sure they feel safe, happy, and loved while you're away. I offer a flexible and stress-free experience for both you and your dog, with plenty of attention, exercise, and fun! Your pup’s comfort and happiness are my top priority. Looking forward to meeting your furry companion and making them feel at home!" I am excited an eager to help out taking care of your furry friends and with 18 years of having pets and three years of experience watching dogs for friends I am willing and able to do what it takes to give your dog a quality experience and help out with whatever is needed. I am a teacher in Chesterfield County so I can be available all day on weekends, Saturday and Sunday, and after 4 PM on week days. I have two dogs, one is a beagle/dachshund mix that is 3 years old and a 10 month smaller sized lab/hound mix that are both under 30 pounds and live in a two floor condo with no yard. I am able to walk dogs and do pop in visits to check on your dogs.

Sitter Profile Image: jakiya p.
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jakiya p.
from
$55
per night
5.0 out of 5 stars
27 reviews
8 repeat clients
6 years of experience
Carver, Richmond, VA, 23220

I am absolutely blown away by Jakiya and could not recommend her highly enough. She communicated like a pro and took exceptional care of my Finn and Vada! And, my house looked cleaner than when I left! I am already preparing to book her for another sit. My Finn and Vada wouldn’t have it any other way.

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Jan H.
Sitter Profile Image: Jacqueline D.
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Jacqueline D.
from
$50
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
10 years of experience
Richmond, VA, 23224

Jacqueline was a great dog sitter! She watched our 2 large dogs for a week. She took the time to meet the dogs beforehand, and receive their care instructions. She sent daily pictures of the dogs and took great care of them! Highly recommend, and will definitely re-book for future trips.

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Sarah P.
Sitter Profile Image: Tiana S.
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Tiana S.
from
$31
per night
5.0 out of 5 stars
5 reviews
5 years of experience
Old Town Manchester, Richmond, VA, 23224

I can’t say enough good things about Tiana! Not only did she take fantastic care of our dog by making sure he was happy, loved, and well looked after, she also took the time to water a dry patch in our lawn. She then cleaned out our fridge whenever it unexpectedly stopped working. That was a huge help. It gave us such peace of mind knowing our home and pup were in such good hands. I highly recommend!

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Finness C.
Sitter Profile Image: Jordan D.
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Jordan D.
from
$40
per night
5.0 out of 5 stars
14 reviews
1 repeat client
10 years of experience
Chesterfield, VA, 23832

I can’t say enough nice things about Jordan. She jumped in at the very last minute and helped me with my 3 cats when my previous pet sitter had a last minute emergency. She was loving and attentive to my home as well as my cats!! Thank you so much!

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Susan H.
Sitter Profile Image: Nancy C.
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Nancy C.
from
$40
per night
5.0 out of 5 stars
3 reviews
1 repeat client
8 years of experience
Richmond, VA, 23224

Nancy did a wonderful job caring for our home and our three very different dogs while we were away. She was responsible, communicative, and great about checking in whenever she had questions. She carefully followed all instructions, and it was clear our dogs were well cared for and comfortable in her care. We came home to happy dogs and a house that was in great shape. We truly appreciated the peace of mind she gave us and would absolutely recommend her to others.

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Mary J.
Sitter Profile Image: Daniel C.
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Daniel C.
from
$35
per night
5.0 out of 5 stars
58 reviews
15 repeat clients
10 years of experience
The Fan, Richmond, VA, 23220

Daniel was awesome as always! Great with our cats, even managed to get our older cat his transdermal medication successfully. He's also respectful of our home- we never feel any anxiety with having him in the space.

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Bethany F.
Sitter Profile Image: Le'Yana O.
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Le'Yana O.
from
$38
per night
4.7 out of 5 stars
16 reviews
8 repeat clients
12 years of experience
Midlothian, Richmond, VA, 23224

Le’Yana was amazing ! My first time using the app to book someone to watch my dog and I don’t regret it ! Very sweet women , definitely would be booking her again . Thank you

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Shanecia D.
Sitter Profile Image: Journei F.
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Journei F.
Star Sitter
from
$28
per night
5.0 out of 5 stars
5 reviews
3 repeat clients
7 years of experience
Richmond, VA, 23234

10/10

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Matt W.
Sitter Profile Image: Victor S.
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Victor S.
Star Sitter
from
$70
per night
4.9 out of 5 stars
32 reviews
11 repeat clients
4 years of experience
The Museum District, Richmond, VA, 23220

Victor did great sitting for Ellie, kept her company all day, listened to her needs, gave her food and her medicine. Would absolutely book him again in the future!

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Elias
Sitter Profile Image: Celeste H.
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Celeste H.
Star Sitter
from
$60
per night
4.9 out of 5 stars
14 reviews
2 repeat clients
15 years of experience
The Museum District, Richmond, VA, 23221

Celeste was an absolutely wonderful dog sitter. She was communicative, thoughtful, and consistently kept me updated, which gave me so much peace of mind while I was away. It was clear she genuinely cared about my dog, and seeing how happy and comfortable my dog was in her presence meant everything to me. I could tell my dog felt safe, loved, and well cared for the entire time. I would absolutely trust Celeste again and highly recommend her to anyone looking for a reliable and caring sitter.

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luanda f.
Sitter Profile Image: christine b.
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christine b.
from
$65
per night
5.0 out of 5 stars
26 reviews
8 repeat clients
8 years of experience
Randolph, Richmond, VA, 23220

Christine was so fantastic taking care of our babies! She was very responsive and cared so deeply about them, some of which are special needs or elderly and require medications, and she took great care to make sure each of their needs were met. She treated them like they were her own. She was respectful of our home and we would highly recommend her!

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Rebecca B.
Sitter Profile Image: Jacob H.
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Jacob H.
from
$60
per night
5.0 out of 5 stars
19 reviews
4 repeat clients
25 years of experience
Oak Grove, Richmond, VA, 23224

Jacob is amazing and extremely mindful of our dogs wellbeing and the upkeep of the house. We love when he comes to sit and have peace of mind that everything is taken care of! Thanks 🫶

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Grace S.
Sitter Profile Image: Nicholas C.
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Nicholas C.
from
$38
per night
5.0 out of 5 stars
5 reviews
10 years of experience
Richmond, VA, 23220

About: My name is Nick and I am a teacher in Chesterfield county looking to use my love for animals as a way to make some extra money over the summer. I have had dogs and cats growing up my whole life and currently have a dog named Bagel and a cat named Friday. I also have lots of experience dog/cat sitting for friends and family over the years ever since I was in high-school. I am a teacher so I won’t be working during the summers so I will have unlimited time during the day/night to take care of your pets and their needs! Once the school year starts I can do weekends and afternoon/nights! I have a lot of energy myself so if your pets love to get exercise/play around I am very up for that. I also try to be very thorough with the pet care instructions and will ask questions/for clarification to ensure I am giving your pet the best care as possible.

Sitter Profile Image: Kaylynn H.
Verified Background Check
Kaylynn H.
from
$50
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
18 years of experience
The Fan, Richmond, VA, 23220

About: I’ve had dogs and animals my entire life. I have a heart for caring for animals and giving them the best life possible. Can help train younger dogs as I have experience training puppies and reactive dogs. 🚨I also have experience and knowledge of working with reactive dogs (barking, etc.). If your dog needs a bit more TLC and patience, I am happy to offer that to your pup. I ask that you describe in detail how to best set your dog up for success during my time with them and what their typical triggers are so that I keep your pup safe and happy. I’m a young professional living in central Richmond VA. I live a leisure lifestyle outside of work in event planning that includes many walks, plant gardening, and reading. I am also known for the occasional hike! Weekends are usually free as well as pockets of time throughout the day and evenings. Dogs are allowed anywhere in my home! I openly welcome couch snuggles (unless owner would rather place and mat training in place). I want to make my space as comfortable as possible for our furry guests, so will make any accommodations necessary for a relaxing stay with me!

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Windsor pet parents share their Rover experiences

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5.0 out of 5 stars

Savannah was awesome! She played with my boys everyday and kept them entertained. She kept them on the same schedule I had them on and her communication was great! I’d definitely recommend to book her when you need overnight sitter

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Jeremiah P.
House Sitting
5.0 out of 5 stars

Ginny took such amazing care of my Tillie-Bean! She kept me updated with plenty of photos and messages, which made being away from my sweet pea so much easier. Tillie had such a great time that I’m pretty sure she’ll be requesting Ginny as her sitter again in the future! 🐾💕

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Jenn B.
House Sitting
5.0 out of 5 stars

Macee was fantastic to have help watch our two dogs (including a 5month old puppy!). She was communicative, sent updates, and overall just great to work with.

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Lauren T.
House Sitting
5.0 out of 5 stars

Nancy did a wonderful job caring for our home and our three very different dogs while we were away. She was responsible, communicative, and great about checking in whenever she had questions. She carefully followed all instructions, and it was clear our dogs were well cared for and comfortable in her care. We came home to happy dogs and a house that was in great shape. We truly appreciated the peace of mind she gave us and would absolutely recommend her to others.

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Mary J.
House Sitting
5.0 out of 5 stars

Bianca and Conrad took excellent care of the pups while housesitting. Excellent communication and lots of pictures. Dogs looked well taken care of and the house looked great. Highly recommend!

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Zohaib A.
House Sitting
5.0 out of 5 stars

Kelly is truly the best catsitter. I love the pictures and updates she sends and she cares for my cat as if she’s her own!

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Claire G.
House Sitting
5.0 out of 5 stars

Erica was incredible as always! I really appreciate Erica, because when she is watching my dog, I do not have to worry about a single thing. She always treats her with love and follows all of her care instructions.

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Kendall V.
House Sitting
5.0 out of 5 stars

I have a very anxious pup who does not do well apart from me. Camryn did so great with him, it has been one of the easiest transitions back home and he seems very calm! My house was also perfectly kept. Very happy and will definitely be a repeat client of Camryn’s if she will stay again!

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Susan M.
House Sitting
5.0 out of 5 stars

Alexis was very communicative and sent lots of updates (which I appreciate!) I came home to a calm, happy dog. I have already booked Alexis again!

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Alison M.
House Sitting
5.0 out of 5 stars

Jill was excellent to work with, super communicative, and was very loving towards our two pups! Highly recommend!

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Lauretta & Joe L.
House Sitting
5.0 out of 5 stars

Liesel was great! One of my giant dogs has high anxiety and I was thankful for good communication and care. I just moved across the country and took my first trip, so my anxiety was high too! Recommend 10/10 and will definitely rebook.

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Norelle W.
House Sitting
5.0 out of 5 stars

Cheyenne did a wonderful job caring for our 3 aussies in our home while we were on vacation. She was very responsive and responsible. We will definitely hire her again for our pet care needs!

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Christina Y.
House Sitting
5.0 out of 5 stars

Charlotte was wonderful with my dog cher as always! She sent me tons of pictures and kept me updated on how things were going. Looking forward to having her stay with us again soon.

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Isabelle W.
House Sitting
5.0 out of 5 stars

Sadie is always great with our pets and was willing to take on sitting for us on a very short notice during an emergency. We are grateful.

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Shiza A.
House Sitting
5.0 out of 5 stars

We’ve used Rebecca many times. She always does an amazing job taking care of our animals. Love the pics that she sends too.

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Justin M.
House Sitting
5.0 out of 5 stars

Jacob and his partner helped look after our very high energy doggie while we were out of town! The house was spotless when we returned and it was clear Billie was in good hands :)

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Kylie H.
House Sitting
5.0 out of 5 stars

Ellea was great with our dog. We appreciated daily updates and pictures! Can't wait to book her again for our next trip. Thank you, Ellea!

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Josh and Amanda S.
House Sitting
5.0 out of 5 stars

Marissa ensured Boris got important time sensitive medications. She sent a couple photos to let me know how he was doing. She is responsible and caring.

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Annie T.
House Sitting
5.0 out of 5 stars

Hana did a fabulous job taking care of my puppy in my home. I could tell she was loved and cared for. The house was in perfect condition upon my return. Nothing but great things to say about Hana and will be using her again in the future!

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Jane A.
House Sitting
5.0 out of 5 stars

Nora sat for us over a long weekend. Our pup, Ruby, was well cared for and we appreciated the good communication throughout.

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Michaela H.
House Sitting
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How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

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 house 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.

House Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Windsor house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, house sitters on Rover respond in under an hour.

Experience can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available in Windsor.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Windsor house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.