Pet Sitting 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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Over 3
pet parents in Windsor have booked pet sitting

Windsor, Find top rated pet sitting

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: Shae M.
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Shae M.
Star Sitter
from
$40
per visit
5.0 out of 5 stars
19 reviews
7 repeat clients
7 years of experience
Suffolk, VA, 23434

Shae is great! She takes care of my large Cane Corso, Misty, when I am out of town on business. She drops by to feed, play with, and walk Misty. Misty, who can be a handful, really likes Shae, and listens to her well. I highly recommend Shae for your dog care needs, particularly if you have a large breed.

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Jay R.
Sitter Profile Image: Nikolaas P.
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Nikolaas P.
Star Sitter
from
$10
per visit
5.0 out of 5 stars
30 reviews
6 repeat clients
15 years of experience
Franklin, VA, 23851

Came over before our trip for a meet and greet with the dogs as well as us. Great communication. Consistent and sent updates regularly. We were able to go 6 hours away for the first time in years without worrying if our fur babies were taken care of. Truly a blessing.

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Ronald H.
Sitter Profile Image: James C.
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James C.
Star Sitter
from
$30
per visit
4.9 out of 5 stars
54 reviews
16 repeat clients
15 years of experience
Suffolk, VA, 23438

Amazing job!!! Very loving to the animals and understanding. Would recommend 100% and will ask for him specifically next time we travel.

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gbuxton63@yahoo.com
Sitter Profile Image: Madison T.
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Madison T.
from
$17
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
13 years of experience
Suffolk, VA, 23434

Awesome sitter. Was very patient and considerate of our baby girl and took well care of her. Also was very helpful and flexible in a last minute change to schedule. Definitely will be picking Madison again on any future trips to watch our pets

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Rafael K.
Sitter Profile Image: Robbyn W.
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Robbyn W.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
11 reviews
5 repeat clients
3 years of experience
Suffolk, VA, 23434

Robbyn is incredibly professional, reliable and respectful of my home, my animals opened up quickly to her, to which I was surprised. I would absolutely book her again.

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Sherry H.
Sitter Profile Image: Taylor K.
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Taylor K.
from
$25
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
8 years of experience
Suffolk, VA, 23438

Taylor was great with my girls. I have a very loving cuddly great pry and she was so good with her. Will definitely rebook in the future. Communication was great also!

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Angela R.
Sitter Profile Image: Chainey L.
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Chainey L.
Star Sitter
from
$14
per visit
5.0 out of 5 stars
11 reviews
4 repeat clients
5 years of experience
Wakefield, VA, 23888

Chainey is amazing. I’m so glad I found her! Jayce gets a midday visit on my longer work days, and I come home to a less stressed pup. Thank you!

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Sara C.
Sitter Profile Image: Kelly P.
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Kelly P.
from
$25
per visit
5.0 out of 5 stars
13 reviews
3 repeat clients
30 years of experience
Courtland, VA, 23837

Kelly always does a great job of taking care of our pets. It’s comforting to know that we have someone who will care for our kids in the same way we would.

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Lindsey F.
Sitter Profile Image: Ashley R.
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Ashley R.
from
$13
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
20 years of experience
Suffolk, VA, 23435

Ashley was great. She was able to fit me in on a holiday weekend last minute and she took good care of my cats, communicated well and took lots of pics!

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Sara D.
Sitter Profile Image: Felicia H.
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Felicia H.
Star Sitter
from
$13
per visit
5.0 out of 5 stars
28 reviews
11 repeat clients
5 years of experience
South Norfolk, Chesapeake, VA, 23324

Felicia took good care of my dog, made sure all the basics were covered and even did us a solid as we forgot something prior to going out of town. A solid, reliable choice for pet care.

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Mari R.
Sitter Profile Image: Avery C.
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Avery C.
from
$22
per visit
5.0 out of 5 stars
156 reviews
25 repeat clients
10 years of experience
Yorktown, VA, 23692

Avery is great!! She had excellent communication and follow-through the entire week of drop-in visits at my house. I loved the personalized notes/report cards she left after each visit. Avery is very trustworthy in your home. Her warm and calm demeanor is perfect for the care of your animals. I knew that my pet was in good hands from the moment I met her… This peace-of-mind allowed me to enjoy my vacation and time with my family even more - knowing my cat’s personal care was being handled with the upmost professionalism back home… I can always tell the level of care a pet sitter gives while I am gone, based on my cat’s behavior and stress level when I return, and my cat couldn’t have been more relaxed - like I never left! I would highly recommend Avery to anyone looking for a quality pet sitter.

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Ryan S.
Sitter Profile Image: REBECCA W.
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REBECCA W.
from
$16
per visit
5.0 out of 5 stars
13 reviews
5 repeat clients
20 years of experience
Suffolk, VA, 23437

Rebeccah has been absolutely amazing with our dogs, Justice and Coco! From the moment we met her, we knew they were in great hands. She is attentive, reliable, and truly cares about the well-being of our pups. Justice and Coco are always happy, well cared for, and relaxed when we return, which says everything about the love and attention Rebeccah gives them. She keeps us updated, follows all instructions, and goes above and beyond to make sure they are comfortable and safe. It gives us so much peace of mind knowing we have someone we can trust completely with our dogs. We highly recommend Rebeccah to anyone looking for a dependable and caring dog sitter!

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Felicia N.
Sitter Profile Image: Kimberly H.
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Kimberly H.
from
$30
per visit
5.0 out of 5 stars
20 reviews
4 repeat clients
20 years of experience
Portsmouth, VA, 23321

Lucy and Ethel were very happy and well taken care of! Thank you

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Kimberly W.
Sitter Profile Image: Alyssa M.
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Alyssa M.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
249 reviews
79 repeat clients
15 years of experience
Indian River, Chesapeake, VA, 23325

Alyssa took amazing care of our cat and sent such cute photos and updates! Our cat was well taken care of, and she even vacuumed and brought him a new toy that he absolutely loved. It is so nice to know that I can enjoy my vacation without feeling too guilty because I know my cat is getting cuddles and play time while I am gone!

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Madi
Sitter Profile Image: DeHaven S.
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DeHaven S.
from
$35
per visit
5.0 out of 5 stars
32 reviews
7 repeat clients
10 years of experience
Carrollton, VA, 23314

DeHaven and Ashlee are Wonderful!!🤩 This was the first time I have left my kiddos with someone other than family. Naturally, I was a little anxious at the thought of arranging it, but that quickly changed once I met them. They took the time to do a meet and greet, and I was instantly confident in my choice and felt totally at peace. They are great with communicating, wonderful with animals (to include the outdoor feathered ones), went above and beyond and even sent pics to us while we were gone!! I just can’t say enough great things about them and the whole experience!! Will definitely use them again!! Thank you Ashlee!!😊

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Harriet C.
Sitter Profile Image: Christine L.
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Christine L.
Star Sitter
from
$27
per visit
4.9 out of 5 stars
151 reviews
53 repeat clients
8 years of experience
Norfolk, VA, 23505

Christine takes great care of my pets. Whether it's an overnight or drop in I know my babies will be taken care of. She does great updates and sends pictures.

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Emily G.
Sitter Profile Image: Kari H.
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Kari H.
from
$25
per visit
5.0 out of 5 stars
20 reviews
4 repeat clients
15 years of experience
Deep Creek South, Chesapeake, VA, 23323

Absolutely wonderful sitter! Made sure my four cats were well cared for and loved while my husband and I were on vacation!

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Molly R.
Sitter Profile Image: Angie S.
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Angie S.
from
$35
per visit
5.0 out of 5 stars
22 reviews
11 repeat clients
40 years of experience
Suffolk, VA, 23434

Angie was great and took great care of our three pups while i was away for work last month! Would highly recommend her for your dogsitting needs!

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Stephanie B.
Sitter Profile Image: Trinity H.
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Trinity H.
from
$10
per visit
5.0 out of 5 stars
17 reviews
2 repeat clients
5 years of experience
Suffolk, VA, 23434

About: I've owned or help own several dogs. My family has 3 currently. I love animals so I volunteer for and ride horses, care for dogs and feed the feral cats in my neighborhood. I'm perfect for someone who needs a quick, cheap, consistent service. Currently available to walk or drop-in with pets from 2-5pm on Wednesdays only. I am a very good listener and a gentle handler. I instill some consistent walk etiquette but I am not a dog trainer! I am here to keep me and your pet walking and safe. I have a fenced in backyard and several parks nearby. My neighborhood is walkable. Your pet will never be far from water, food, space or comfort.

Sitter Profile Image: Jane C.
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Jane C.
from
$40
per visit
5.0 out of 5 stars
9 reviews
1 repeat client
17 years of experience
Suffolk, VA, 23434

About: My first two pets were 2 doggies at 9 months old. I had them for 17 years until they left for doggy heaven October 2024 and February 2025… I am not ready to fully commit again quite yet so decided babysitting and loving on others’ furbabies will help the healing. Work from home all week. Will be able to take care of them in home and overnight if needed! I will accomodate to all requests and needs. Will appreciate details such as age, allergies, health, likes and dislikes. Will treat your baby/babies like they are my own. Will walk them as I have a dog friendly neighborhood as well as a newly built dog park. The backyard is also fenced.

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The median cost per visit for pet sitting in Windsor is $20

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 pet 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 pet sitting - Windsor

Select a filter and find qualifying sitters offering pet sitting.

Sitters in Windsor average 6
repeat pet sitting clients

FAQs for Drop-In Visits - Windsor

Frequently asked questions about Rover

The average cost for Pet Sitting in Windsor on Rover is $26.75 per visit (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Pet 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 Pet Sitting. For more information on service fees, click here .

As of August 2026, there are 2,238 sitters on Rover offering Pet Sitting across Windsor. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Windsor stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.

If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.

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 .

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.

Yes, you can find sitters who have experience with handling special pet needs in Windsor. On Rover:

  • 96% of sitters can help with special care needs
  • 99% 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.

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.

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