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 41
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: Nikolaas P.
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Nikolaas P.
Star Sitter
from
$10
per visit
5.0 out of 5 stars
27 reviews
6 repeat clients
15 years of experience
Franklin, VA, 23851

Nik is a true professional who genuinely cares about the pets he’s visiting and has so much knowledge to share! We have a senior mixed breed who is nervous around new people and Nik was patient with us (as we were using this service for the first time) and our girl who was understandably a little anxious about someone new being in her house. He has amazing communication skills and is incredibly reliable.

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Ciara M.
Sitter Profile Image: Shae M.
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Shae M.
Star Sitter
from
$40
per visit
5.0 out of 5 stars
18 reviews
5 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: Abigail T.
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Abigail T.
from
$20
per visit
4 years of experience
Windsor, VA, 23487

About: I have had dogs and cats in my life since i was a baby! They have always been my bestfriend! I currently have 1 dog (a golden retriever) and 2 cats. And I’ve house sat for many many fiends for long periods of time. In my eyes i don’t see them as just animals but another member to the family. And that’s how i would treat your fur babies! You should feel comfortable leaving your fur babies in the hands of someone else when life becomes busy or you just need to get away. and i promise I will give your babies all the love and attention they deserve! I work weekdays but i get off early almost everyday with very flexible hours and I’m off every weekend. My work schedule is pretty flexible. I have loads of free time! I have a fenced in yards. My dog is an inside dog (the house belongs to her lol) i have 2 cats that wants to sit on everyone lap. My dog has full access to the house when I’m home and only the downstairs when I’m gone. The cats roam the house as they please but they love to be by my side more than anything! My dog spends so much time outside playing and gets a long walk every day!

Sitter Profile Image: Christian G.
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Christian G.
from
$25
per visit
5.0 out of 5 stars
1 review
8 years of experience
Suffolk, VA, 23434

Christian did a great job with our cat drop-in visit. He was on time, made sure their water was topped off, spent time playing with them, and sent plenty of pictures and updates while we were away. It was obvious he genuinely cared about making sure they were comfortable and cared for. We’d definitely book with him again and highly recommend him to anyone looking for a reliable sitter.

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

Fantastic drop-in service! Timely and communicative. I would be continuing with her if I still needed weekly walks.

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Meg I.
Sitter Profile Image: Chainey L.
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Chainey L.
Star Sitter
from
$14
per visit
5.0 out of 5 stars
10 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: Alexa N.
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Alexa N.
from
$12
per visit
4.0 out of 5 stars
4 reviews
1 repeat client
5 years of experience
Suffolk, VA, 23435

About: With many years of hands-on experience, I specialize in more than just dog sitting. I provide tailored care for every stage of life. From high-energy puppies needing structure and basic training to senior dogs requiring gentle attention and medication support, I’ve cared for them all. My calm, compassionate approach ensures pets feel safe, loved, and right at home, even when you're away. Pet care is a core part of my daily life. I plan my schedule around it. Whether it’s morning walks, midday playtime, or evening feedings, I’m consistently available to provide structure and attention. I treat every pet with love to ensure each one gets the time and focus they deserve. Your pet’s safety and comfort are my top priorities. In my home, I provide a calm, pet-friendly space with secure areas for play, rest, and relaxation. I maintain a clean, non-smoking environment and follow any dietary or medical routines you provide. When caring for pets in your home, I treat your space with respect and follow your instructions closely to keep your pet in their familiar routine. I’m fully insured and keep you updated with regular photos and check-ins, so you can travel with peace of mind.

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: 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

Rebecca did an amazing job caring for justice. She made sure to cater to her every need, even adjusting times when needed. I usually kennel justice when I go away so this was my 1st time using this type of service and I couldn’t be happier. Thank you Rebeccah for taking such good care of my baby and calming my nerves.

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Felicia N.
Sitter Profile Image: April L.
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April L.
from
$12
per visit
5.0 out of 5 stars
21 reviews
12 repeat clients
20 years of experience
Smithfield, VA, 23430

Stellar care of my pup Ava as always. 🙏🏽❤️

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Buck A.
Sitter Profile Image: Kelsie R.
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Kelsie R.
from
$18
per visit
5.0 out of 5 stars
7 reviews
10 years of experience
Suffolk, VA, 23434

Kelsie did an excellent job while I was out of town for a week. My kitties experienced a bit more separation anxiety than usual, and ended up making a huge mess of the front room. Kelsie informed me of it immediately and was super understanding of it. Since I wasn’t around my phone during that visit and couldn’t tell her where the cleaning sprays were, she waited till I was able to tell her where the items were. Then came back the next day to further clean up the floors! One of my kitties is very weary of new people and she did great with making sure not to stress her out too much.

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Faith J.
Sitter Profile Image: DeHaven S.
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DeHaven S.
from
$20
per visit
5.0 out of 5 stars
32 reviews
7 repeat clients
10 years of experience
Carrollton, VA, 23314

Ashley was great with my four kitties. She even managed to get one of the shy ones to join in the fun. She took great care and spent a lot of time playing with my two high energy cats (which spared my furniture). Would definitely book again.

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Heidi F.
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: Cynthia S.
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Cynthia S.
from
$20
per visit
5.0 out of 5 stars
4 reviews
5 years of experience
Suffolk, VA, 23434

About: What makes me different is the level of care, patience, and versatility I bring to every animal I look after. I’m not just here to cover the basics—I focus on making sure each animal feels safe, understood, and genuinely cared for. I’m experienced with a wide range of animals, from dogs and cats to large and farm animals like horses, goats, and chickens. This means I’m comfortable handling different routines, environments, and responsibilities with confidence. I also have a strong understanding of pets who need extra support, including seniors and those with anxiety. I take a calm, gentle approach, move at their pace, and prioritize building trust so they feel secure while you’re away. I pay close attention to small details—changes in behavior, appetite, or mood—so nothing gets overlooked. Combined with reliable communication and consistent updates, you can feel confident your animals are in capable, caring hands. Animals have been a constant part of my life, and caring for them is something I take seriously and genuinely enjoy. I provide reliable, attentive pet sitting for families who want their pets to feel safe, comfortable and loved while away. Whether it is daily walks, playtime, medication, or simply keeping them company, I focus on creating a calm, lovable and predictable routine that helps them feel secure. I’ve worked with dogs of all sizes, cats with all different personalities, small and large animals who need gentle, constant care. I pay close attention to behavior changes, eating habits, and comfort levels so you always know how your pet is doing. Communication matters a great deal, so I send updates, photos, and notes to keep you connected. My goal is simple, to treat your pet like they are my own and make those time away as stress-free as possible! I provide loving, reliable sitting, giving your pet a safe, calm, and comfortable place to stay while you’re away. I treat them as part of my own pets. Keeping routines consistent and their environment peaceful.

Sitter Profile Image: Melody & Matthew D.
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Melody & Matthew D.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
83 reviews
42 repeat clients
10 years of experience
Suffolk, VA, 23434

Melody has done a great job of taking care of Victoria. We are pleased to have her. I feel very fortunate to have Melody and Matthew taking care of our Victoria

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Jay B.
Sitter Profile Image: Lauren K.
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Lauren K.
from
$18
per visit
5.0 out of 5 stars
5 reviews
2 repeat clients
20 years of experience
Suffolk, VA, 23434

Lauren took care of my sweet Bailey like she was her own. From the moment they met, Bailey was completely smitten, and I can’t blame her. Lauren has this calm, loving energy that dogs (and people) instantly trust. She made sure Bailey was happy, safe, and spoiled with attention, and I never once had to worry. She’s attentive, patient, and somehow knows exactly what a dog needs before they even ask for it. I swear Bailey was happier than ever when I came back from work... probably because she spent her days with someone who truly loves the animals she cares for.

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Addie L.
Sitter Profile Image: Taylor K.
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Taylor K.
from
$25
per visit
5.0 out of 5 stars
2 reviews
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: Gabby B.
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Gabby B.
from
$20
per visit
5.0 out of 5 stars
2 reviews
2 repeat clients
15 years of experience
Windsor, VA, 23487

About: I enjoy fostering dogs to help get more information about their personalities and in turn help them get adopted. I have also been a dog sitter for family and friends for years. I enjoy practicing my dog training hobby. I believe the more training a dog has the happier they will be. They will know their boundaries and what makes their human happy thus creating a positive environment. I currently work full-time from home therefore daycare or walks are the most ideal services for me. If we have a good established relationship (human to human and dog to human) I am open to overnight says. I have a larger fenced yard however the fence is vertically challenged. I like and want to go for a couple walks a day. I have a daughter who loves dogs and is very good with them. She's a gentle and loves to help train, feed or just sit and pet them.

Sitter Profile Image: Daniela U.
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Daniela U.
from
$25
per visit
5.0 out of 5 stars
8 reviews
1 repeat client
9 years of experience
Suffolk, VA, 23437

Wonderful! Thank you for dropping in to take Harley out.

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Jaclyn R.
Sitter Profile Image: Breanna V.
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Breanna V.
from
$20
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
18 years of experience
Suffolk, VA, 23434

About: I took a break from pet sitting for awhile due to moving, but I am back and available on weekends! I have loved and cared for dogs since I was a kid. Back in my home state I ran a doggy-day care and began grooming and shadowing at dog shows. I have mainly had Australian Shepherds, but have also had German Shepherds, Pitbulls, Poodles, Beagles, and Labs. I love dogs, honestly, more than people most days. In the past I have trained dogs and competed in dog agility trials. I currently have three dogs, an Australian Shepherd, who is my heart and soul, a German Shepherd Husky who is the sweetest girl, and a Rough Collie who lives up to his name, Taz. I can handle any size dog, any temperament, and ensure they get the care and attention they deserve. Dogs are such amazing animals that can help us overcome even our worst days, I want to make sure your dog is taken care of while you're away so you have less to worry about at the end of the day. I work full time, so I am only available on weekends at this time. My weekends are flexible to accommodate travel schedules, drop-in visits, and walks. I follow your instructions on how you want your dog taken care of. Thats your baby, and I am here to love them as you do.

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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 $22.2 per visit (as of July 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 July 2026, there are 2,260 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:

  • 95% 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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