Pet Sitting & Drop Ins In Windsor

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Windsor pet sitters

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Nick I.
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Nick I.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
36 reviews
12 repeat clients
10 years of experience
Fulton, Richmond, VA, 23231

Nick’s care and communication have been absolutely phenomenal, and I truly appreciated it. I could tell Sebastian felt well loved and cared for through the pictures that he sent during my time away! This was my first time using Rover, and I'm sold. I'll definitely keep Nick in mind as I travel frequently, and we've had some family shifts so care is not always as readily available.

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Ashley W.
Sitter Profile Image: Jasmine H.
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Jasmine H.
from
$20
per visit
5.0 out of 5 stars
176 reviews
49 repeat clients
15 years of experience
Richmond, VA, 23224

Jasmine was reliable, kind and soo helpful with coffee !! I loved the picture and prompt updates ! I will definitely be rebooking with her again

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Cortney S.
Sitter Profile Image: Danyelle H.
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Danyelle H.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
67 reviews
19 repeat clients
20 years of experience
Shockoe Bottom, Richmond, VA, 23223

Danyelle is AMAZING!!! Took such great care of my boys over a holiday. Gave me daily updates and even put up with some of their eating "quirks", which isn't always easy. But she was super patient with them and gave them all the love they needed while I was gone. I was so super happy and relaxed to know they were in such great and caring hands. Heck, even just the trek to my trash can for litter box cleaning was an extra effort in and it's self. Can't recommend Danyelle enough!

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Mike T.
Sitter Profile Image: Nicole D.
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Nicole D.
from
$20
per visit
5.0 out of 5 stars
9 reviews
3 repeat clients
12 years of experience
Richmond, VA, 23220

About: I’ve taken care of dogs my whole life of all sizes. I grew up with a great pyranees/ border collie and have a dog of my own who is a dachshund. I dog sat for my neighbor, friends, and relatives frequently. I also have experience in sitting for cats as well. I can also help your dog learn new tricks! I taught my dog how to sit, stay, lay down, paw, roll over, follow, and wait all within 6 months. I am currently a part-time employee and have a dog of my own, so I have plenty of time and experience in pet care to give your furbaby the care they deserve! I’m flexible to what they need. Whatever needs you have for your furbaby I can meet! My dog is very particular, so I am patient, willing and understanding to what your pet needs.

Sitter Profile Image: Alyssa M.
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Alyssa M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
33 reviews
11 repeat clients
15 years of experience
Chimborazo, Richmond, VA, 23223

Alyssa was great with my cat, who experiences separation anxiety. She did a wonderful job and sent me pics of my kitty getting skritches. I appreciate her care.

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Rebecca M.
Sitter Profile Image: Sidney D.
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Sidney D.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
56 reviews
17 repeat clients
20 years of experience
The Fan, Richmond, VA, 23220

Sidney is great with our puppy and was very accommodating to do a drop-in on short notice. Would recommend her to anyone looking for drop-ins and dog walks!

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Kyle D.
Sitter Profile Image: Mitchell I.
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Mitchell I.
from
$20
per visit
2 years of experience
Richmond, VA, 23225

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: Holland H.
Verified Enhanced Background Check
Holland H.
Star Sitter
from
$14
per visit
5.0 out of 5 stars
64 reviews
16 repeat clients
8 years of experience
Richmond, VA, 23220

Holland did a wonderful job of looking after my cat, Lucy. She was always on time, took plenty of pictures/videos, and was even able to give her eye drops. I knew that Lucy was in good hands, and appreciated her thoughtfulness. Will definitely rebook again!

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Lauren D.
Sitter Profile Image: Alexander S.
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Alexander S.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
33 reviews
8 repeat clients
47 years of experience
Old Town Manchester, Richmond, VA, 23224

Alexander was awesome! My silly, hyper pup warmed up to him well and he made sure my big oy was taken care of without any deviations from our routine. I will be planning on booking Alexander soon!

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La'Shanta J.
Sitter Profile Image: Cheyenne B.
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Cheyenne B.
from
$22
per visit
5.0 out of 5 stars
3 reviews
3 repeat clients
15 years of experience
Woodland Heights, Richmond, VA, 23225

About: Hi! I’m Cheyenne, a lifelong animal lover with hands-on professional experience caring for dogs of all sizes, breeds, and temperaments. I previously worked at a kennel-free dog boarding facility, where I helped care for multiple dogs at once in a safe, supervised environment. I’ve also worked as a full-time dog walker and pet sitter, providing daily walks, drop-in visits, feeding, medication administration, and lots of attention and playtime. Animals have always been part of my life—I’ve grown up with dogs and cats and currently care for my own pets as well. Because of my background in both professional animal care and customer service, I understand how important communication and trust are when someone else is caring for your pet. What you can expect when your pet is with me: • Reliable, on-time care • Regular photo and text updates • Safe handling for dogs with different temperaments • Experience with multi-dog households • Lots of attention, enrichment, and play Whether your dog needs a walk while you’re at work, drop-in visits while you’re away, or extra love and attention, I treat every pet like they’re my own. I’d love to meet you and your furry family member! I work a hybrid office jobs with very flexible hours. When I do go into the office, my office is dog friendly so I can bring a furry friend along if they enjoy the socialization! I care for pets in their own home so they can stay comfortable in a familiar environment and maintain their normal routine. For drop-in visits and house sitting, I follow the owner’s instructions closely, including feeding schedules, walks, medications if needed, playtime, and any specific routines your pet is used to. During visits, I make sure pets get the attention, exercise, and enrichment they need, whether that’s a long walk, playtime, or just companionship. I also make sure basics like fresh water, clean feeding areas, and litter boxes are taken care of. For dog walks, I focus on safe handling, appropriate exercise for your dog’s energy level, and making sure they return home happy and settled. I always send updates and photos so you know how your pet is doing while you’re away. My goal is to make sure your pet feels safe, cared for, and loved while keeping you informed and at ease.

Sitter Profile Image: Jeffrey H.
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Jeffrey H.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
94 reviews
22 repeat clients
34 years of experience
The Fan, Richmond, VA, 23220

Jeff provided multiple days of feeding, cuddle time, walks and loving attention for our dog. The photos he sent helped us feel at ease knowing our boy was safe and happy. We appreciated his responsibility and updates!

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Laura F.
Sitter Profile Image: Kacey G.
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Kacey G.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
44 reviews
12 repeat clients
12 years of experience
Upper Shockoe Valley, Richmond, VA, 23223

Kacey was so great with Rosie! She made sure she had everything she needed and took lots of photos for us. Definitely recommend her for all your pets!

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Seana C.
Sitter Profile Image: Elijah S.
Verified Background Check
Elijah S.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
249 reviews
74 repeat clients
4 years of experience
Eastview, Richmond, VA, 23223

Elijah was great! Took wonderful care of my cat. Ran out her energy with every visit, let her take time to acclimate, and even went out on the catio with her. I can tell he’s a loving cat parent and passes that care on to his rover animals too!

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Lexi B.
Sitter Profile Image: Ivana M.
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Ivana M.
from
$20
per visit
5.0 out of 5 stars
31 reviews
13 repeat clients
10 years of experience
Shockoe Bottom, Richmond, VA, 23223

About: I offer daycare, overnight stays, walks and check ins! I’ll make sure your pet gets the love and attention they deserve. Frequent trips to the dog park and lots of long walks. As a long time pet owner I know how important it is to care for your pet properly and be able to trust they are in good hands. I have experience caring for old dogs as well as sick dogs that require lots of attention and medication. I am experienced in caring for puppies. Will provide hourly check ins when requested including photos. Dogs allowed on furniture. Will never leave them alone. Available on short notice. Hourly Over 10 years experience. Rest assured your pet will be in very good hands staying with me.

Sitter Profile Image: ashley g.
Verified Enhanced Background Check
ashley g.
from
$14
per visit
5.0 out of 5 stars
29 reviews
10 repeat clients
7 years of experience
Oak Grove, richmond, VA, 23224

Ashley was terrific with my cat Grace! Ashley clearly gave my cat the care and attention any pet owner would hope their pets receive while their owners are away!

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Meredith G.
Sitter Profile Image: Deanna S.
Verified Background Check
Deanna S.
from
$18
per visit
5.0 out of 5 stars
46 reviews
2 repeat clients
15 years of experience
Richmond, VA, 23224

Deanna was great! I was away longer than usual but felt confident all was well because of Deanna’s detailed updates. Everything was perfect when I came back. I would definitely use her again.

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Lucie B.
Sitter Profile Image: Maggie D.
Verified Enhanced Background Check
Maggie D.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
22 reviews
4 repeat clients
20 years of experience
Monroe Ward, Richmond, VA, 23220

Maggie is so kind and wonderful with my two cats. She’s so thoughtful and detail oriented and I really appreciated her help while we were away. Maggie is a great rover!

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Valerie M.
Sitter Profile Image: Annabella C.
Verified Enhanced Background Check
Annabella C.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
21 reviews
8 repeat clients
4 years of experience
North Chesterfield, VA, 23237

Annabella was able to help with Elvis very last minute and she was so great and patient with him. Would absolutely recommend her, she was fabulous !

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Ruby V.
Sitter Profile Image: Destiny R.
Verified Enhanced Background Check
Destiny R.
from
$10
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
9 years of experience
Richmond, VA, 23234

About: I have two dogs of my own one of which I trained to be my personal service dog. My second dog we originally were fostering and we adopted her because she fit into our family perfectly and became our other pups best friend. I actively foster puppies and kittens. I’ve done crate training and all the potty scaries with puppies. I’m extremely patient with them and try to meet each dog where they are at. I have experience giving medications to pets as one of my cats has to have daily oral medication. I love my pets and would treat yours as if they were my own 🖤 I have a very flexible schedule and I’m on the road and I have free time during the day and evenings where I am able to fit pet care-sitting into my schedule. I’m a very attentive pet parent myself and don’t typically leave my own dog unattended outside in the yard and I try to be very interactive and engage so they can play. I have 3 cats and enjoy playing with them and spending time with them so they feel cared for.

Sitter Profile Image: Peyton W.
Verified Enhanced Background Check
Peyton W.
from
$20
per visit
5.0 out of 5 stars
12 reviews
3 repeat clients
20 years of experience
Cottrell Farms, Richmond, VA, 23234

Peyton fed our cat every night for four nights while we were away on vacation. Our cat is typically very shy and will hide when there are strangers around, but she trusted Peyton! We were sent photos of her every night with updates on how she was doing. I will definitely be booking her services again in the future!

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Annie T.
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Windsor pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Abby is a top-tier petsitter! She watched Coconut while I was away, and from the moment I left, I had complete peace of mind. She was incredibly conscientious and thorough — you can tell she genuinely cares about the animals in her care. Her consistent and detailed communication with each visit eased my mind. Without fail, she checked in twice a day with photos and detailed recaps of each visit. Seeing Coconut happy and well cared for made my time away so much more enjoyable. She went above and beyond in every way. I will absolutely be hiring Abby again and would recommend her without hesitation to anyone looking for a trustworthy, attentive, and loving petsitter. Coconut was happy and lucky to have her! 🐱

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Jeb T.
Drop-In Visits
5.0 out of 5 stars

Heather was great! She was communicative, responsive, and prompt when coordinating care instructions and when reaching out in response. She followed instructions and provided consistent and helpful updates. I loved getting updates and photos throughout the day. It helped give me peace of mind while being away for 12 hours. I absolutely recommend her, and look forward to a repeat booking in the future.

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Elizabeth S.
Drop-In Visits
5.0 out of 5 stars

We asked Grace to check in on our crazy orange cat a few times while we were out of town pretty last-minute, and she exceeded all expectations! She sent lots of pictures and gave great summaries each time she visited. Our cat hates to be alone for too long, and it was such a relief to know that Grace was giving her some much-needed love and attention! We'd definitely use Grace's services again in the future.

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Emily B.
Drop-In Visits
5.0 out of 5 stars

Kade communicated well the entire stay, sent plenty of pictures and told me everything I wanted to know regarding my kitty. I couldn’t have asked for a better person to work with her.

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Lydia H.
Drop-In Visits
5.0 out of 5 stars

Erica was on time for visits and took great pictures! I felt very comfortable entrusting her with Clover after our meet and greet.

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Katie G.
Drop-In Visits
5.0 out of 5 stars

Danyelle was amazing with our indoor and outdoor cats, she sent a lot of pictures and details about each visit. I would recommend Danyelle to others and will be booking her for pet sitting again!

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Catherine M.
Drop-In Visits
5.0 out of 5 stars

Alyssa was wonderful! She took my request fairly last minute, and shared lots of photos of my cat while I was away.

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Angela P.
Drop-In Visits
5.0 out of 5 stars

Emily was professional & friendly, and the cats--especially Phoebe--certainly loved her! One of our kitties had a bit of a medical emergency and Emily handled it with grace and care. Could not recommend her enough! :)

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Kaity M.
Drop-In Visits
5.0 out of 5 stars

Nick is the best! He’s great with Chico and always excited to see him. He keeps me updated on the visit and often says yes to my last minute requests. So grateful to have him watching Chico!

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Claire K.
Drop-In Visits
5.0 out of 5 stars

Per usual, Kelly's the absolute best at handling our cantankerous old man cat. I'd even go as far as saying she's growing on him, which no one has achieved before in his 15 years on this planet. Either way, we love Kelly even if Mowgli doesn't (because he hates everything).

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Jessica V.
Drop-In Visits
5.0 out of 5 stars

Kathleen, you're such a treasure and Henry the cat and I will both miss you so much! Thank you for being so kind, so caring, and so reliable for the past year!! We wish you the best!

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Zoe M.
Drop-In Visits
5.0 out of 5 stars

Kelly was great. She responded quickly to my initial request and changed dates when requested. My old cat responded well to her initially and obviously enjoyed her as indicated by the videos provided after every visit.

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Marianne M.
Drop-In Visits
5.0 out of 5 stars

Absolutely amazing! My dog is not always good with strangers but she loved them immediately. They were so great with her. They responded to messages quickly and listened to any pet requests. It was a 20/10 experience. I’d 100% recommend them to anyone who needs their pet watched or walked. They’re amazing people!

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Prestina G.
Drop-In Visits
5.0 out of 5 stars

Jacob helped me out on short notice, coordinated seamlessly with another sitter, and sent photo updates at every check in! He is calm and respectful and is great with Billie :)

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Kylie H.
Drop-In Visits
5.0 out of 5 stars

I’m grateful for Morgan’s service! Looks like all went well with the pup 🐶 I would definitely rebook in the future.

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Anthony G.
Drop-In Visits
5.0 out of 5 stars

Nora took care of my cat while I was gone. She gave my cat her anxiety medication every evening with food, change her water out and cleaned her litterbox. I’m glad she was available to help. Thank you!

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Kellie B.
Drop-In Visits
5.0 out of 5 stars

Hana is amazing with my husky pack! Very communicative and patient with all their big personalities. Would recommend her to anyone

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Kaitlyn M.
Drop-In Visits
5.0 out of 5 stars

Virginia was an amazing caregiver for my guy Pancho. She was communicative and caring throughout the process, and went the extra mile to ensure that he was cared for and that I had peace of mind. I would 100% lean on her again for care.

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Jay M.
Drop-In Visits
5.0 out of 5 stars

Rose was amazing! Very responsive and my cats loved her!! She sent me daily photos and notes from checking on my pets and I would definitely use her services again!

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Anastasia B.
Drop-In Visits
5.0 out of 5 stars

Mindy has been an excellent and reliable to work with. She took great care of our two cats while we were away for a week. She was very respectful of our home and went above and beyond to make our experience much better. I highly recommend working with her.

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Dlshad O.
Drop-In Visits
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Pet Sitting FAQs

Frequently asked questions about Rover

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

If you have an active request or have booked a service with a pet 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 pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.

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

Rover makes it easy to find Windsor pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:

  • Pets of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Pets who’d love to socialize with their pet sitter’s pets

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet 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 pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.