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 27
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: Madelyn C.
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Madelyn C.
from
$15
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
15 years of experience
Windsor, CT, 06095

Madelyn was great! She communicates well and took great care of our very anxious dog. Will definitely use in the future.

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Casey S.
Sitter Profile Image: Nazim M.
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Nazim M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
75 reviews
20 repeat clients
10 years of experience
Windsor, CT, 06095

About: I’ve had my dog Kal for nearly a decade now. He was a rescue from the South. I have experience fostering dogs including those with special medical needs. I am comfortable administering oral medication and injections. I’ll be working from home indefinitely and I just moved to a new house with a large fenced in yard. I have a 9 anda half year old puppy named Kal-El and while I would love to get another dog for him to play with, dog sitting is the best option at the moment. I’ll love your dog like my own!!! Working from home allows me to be able to take your dog out for walks frequently. Northwest Park is close to me so your pets will have plenty of exercise! And with a dog and a large yard, your dog will have plenty of space and opportunity to socialize. Dogs are allowed on the furniture unless you don’t want them there.

Sitter Profile Image: Jalah C.
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Jalah C.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
7 years of experience
Windsor, CT, 06095

I had an excellent experience with Jalah and couldn’t be happier with the care they provided. From the very beginning, she was punctual and arrived exactly at the scheduled time, which immediately gave me confidence and peace of mind. Jalah followed all of my instructions carefully and paid close attention to the details of my pet’s routine, which I truly appreciated. It’s clear she takes her responsibility seriously and genuinely care about the animals she look after. What stood out the most was their communication.Jalah kept me consistently updated, especially during my pet’s transition to being with someone new in my home. Those updates made a huge difference and reassured me that everything was going smoothly. Overall, I highly recommend Jalah to anyone looking for someone reliable, attentive, and communicative. I would absolutely trust her again in the future!

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Leti L.
Sitter Profile Image: Jesey M.
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Jesey M.
from
$26
per visit
5.0 out of 5 stars
16 reviews
5 repeat clients
7 years of experience
Windsor, CT, 06095

Jesey checked in on my cat for a week and I couldn't have been happier with his drop-in visits. I appreciated how thorough his Rover Cards were and had great peace of mind knowing my cat was taken care of in my absence. I would definitely hire Jesey again!

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Erin S.
Sitter Profile Image: Sarah E.
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Sarah E.
Star Sitter
from
$32
per visit
5.0 out of 5 stars
40 reviews
18 repeat clients
16 years of experience
Windsor, CT, 06095

About: I had my own wonderful dog for 16 years. My yard is spacious so your dog has plenty of room to run around and play. Big or small dogs are okay with me. I am an animal lover of all kinds and have experience taking care of other types of animals like rabbits, guinea pigs, and cats. PLEASE NOTE: I do not watch unspayed/unneutered dogs I will charge a late fee if you are 30 minutes over the agreed ending time I am a full time student who takes my classes online. I have a flexible schedule so I have plenty of time to get outside to walk and play with dogs. I do have a fence in backyard. My backyard has plenty of space as well for your dog to explore. I am a big animal lover and I have multiple years of experience taking care of them.

Sitter Profile Image: Liz W.
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Liz W.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
92 reviews
36 repeat clients
20 years of experience
Windsor Locks, CT, 06096

I had an emergency where i had to go the hospital where i ended up staying for 8 days. Liz was an absolute life saver and stepped in to take care of my fur babies I received updates daily. That helped me so much to relax and be able to heal in the hospital. I came home to healthy happy fur babies. Liz is WONDERFUL with animals. I highly recommend her!!! -Daryl

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Daryl W.
Sitter Profile Image: Jordan C.
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Jordan C.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
54 reviews
19 repeat clients
6 years of experience
East Hartford, CT, 06108

Our cats are doing well under Jordan’s drop in visits. She communicates the schedule well with us & sends photos. Reaaly appreciates her help!

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Anya N.
Sitter Profile Image: Maegen C.
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Maegen C.
from
$15
per visit
4.5 out of 5 stars
2 reviews
25 years of experience
Windsor, CT, 06095

Maegan was very attentive to my pups while I was gone and ensured they were happy, fed, and cared for. She kept in touch and made sure I was kept informed throughout. I would definitely hire her again!

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Shaina S.
Sitter Profile Image: Jessica & Christopher F.
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Jessica & Christopher F.
Star Sitter
from
$27
per visit
4.9 out of 5 stars
136 reviews
60 repeat clients
20 years of experience
Windsor, CT, 06095

Jessica & Chris are wonderful, they humored me with a meet & greet and right away the dogs were comfortable. I got lots of texts and pictures which made me smile so much. They provide the same love my husband and I would give my three girls. For years I boarded my dogs and now with a third it's quite expensive and honestly I have never been in love with the idea because the feedback so often is negative. I feel my babies are themselves and much happier in their own home. I'm very happy to have found Jessica and will look forward to asking for their help in the future. Thank you for everything!

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Lynn D.
Sitter Profile Image: Andrea C.
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Andrea C.
from
$25
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
13 years of experience
Manchester, CT, 06042

Andrea is great! She communicated throughout the entire process. She kept me informed on how everything was going. She sent pictures showing her interaction with Snuggles. Although, she wasn’t booked to care for the cat, she notified me of his mischievous behavior. I will definitely book with Andrea again. Thank you Andrea!

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Tashima C.
Sitter Profile Image: Le'Andra M.
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Le'Andra M.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
28 reviews
13 repeat clients
20 years of experience
Asylum Hill, Hartford, CT, 06105

This was the first time I booked Le'Andra to do daily check-ins on my cat Gabby while I was out of town. She was great! Le'Andra always stayed in communication with me by text. And she did her best to still take care of my cat while also dealing with the storm and very cold temperatures we recently had. Le'Andra is nice and very friendly. I would definitely request her again the next time I need a cat sitter, and would also recommend her to anyone considering booking her on Rover.

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Chris P.
Sitter Profile Image: Mariah L.
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Mariah L.
from
$25
per visit
5.0 out of 5 stars
12 reviews
5 repeat clients
10 years of experience
Windsor, CT, 06095

My job calls me in from time to time with little time to plan for a sitter. She is available to me even on very little notice. My dog is smiling in all the picture updates which makes me feel so good!

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Lexy M.
Sitter Profile Image: Caitlyn C.
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Caitlyn C.
from
$20
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
South Windsor, CT, 06074

Caitlyn was amazing. Super attentive to our two boys Arthur and Finnegan and took a ton of pictures:) I will definitely be contacting her in the future!

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Carrie P.
Sitter Profile Image: Sophie M.
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Sophie M.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
37 reviews
19 repeat clients
10 years of experience
Windsor Locks, CT, 06096

Sophie was so great with our dog Luna!!! She was always on time for her drop ins and was considerate enough to always send us pictures and thorough updates. We could not recommend Sophie more and we would be lucky to have her watch our Luna again. Thank you Sophie!

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Diana M.
Sitter Profile Image: Erica & Chris G.
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Erica & Chris G.
from
$28
per visit
5.0 out of 5 stars
16 reviews
6 repeat clients
20 years of experience
Windsor, CT, 06095

Erica was awesome! Very punctual provides great details and pics.

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Luis N.
Sitter Profile Image: Kathryn H.
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Kathryn H.
from
$22
per visit
5.0 out of 5 stars
4 reviews
15 years of experience
Downtown, Hartford, CT, 06120

About: I have taken care of animals for 15 years and I am very passionate about making animals feel safe, comfortable and loved. I grew up with both cats and dogs and so I am able to take care of both. From pugs, mastiffs, labradors, to cats, I can do it all. I give medication, deep-clean litter boxes, play with you pets and overall make sure your pet feels at ease while you’re away. I am currently a full time employee that travels every Thursday-Saturday so I have a lot of free time at the beginning of the week. I always get up early to make sure I’m taking care of me and my cat’s needs and am able to extend that care to your animals as well. When I do a drop-in visit, I always do a sweep around the main areas of the house to ensure that everything is in order. For dogs, my main priority is to take them out, check their water bowl and play with them to make sure they have the care they need for the day. For cats, I will always check their litter boxes to see if it needs any scooping, I will also check their food and water bowls and fill them up if needed. Like dogs, I will respect their boundaries and play with them to ensure they’re comfortable.

Sitter Profile Image: Ashley S.
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Ashley S.
from
$20
per visit
5.0 out of 5 stars
21 reviews
5 repeat clients
29 years of experience
Windsor, CT, 06095

About: I've helped take care of multiple clients and had a dog of my own my whole childhood and have loved taking care of others animals by cooking for them, playing with them and taking pictures! I'm a stay at home mom with 4 and 8 year old kids so we enjoy walking and playing with the dogs. My husband works from home and my brother lives with us at our house, so we have plenty of space and time for attention. i moved into a house three months ago and there is plenty of yard space, a back deck, and room for multiple dogs to have their own space. We live on a cuddle sack, so it’s also great walking dogs down and back.

Sitter Profile Image: David S.
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David S.
from
$20
per visit
12 years of experience
Windsor, CT, 06095

About: I’ve taken care of my dog, AKA my brother, for 12 years from pup, to angel. I’ve never had any siblings so he was all I had. But I learned a lot about being compassionate towards animals through my short time with him. I believe I can provide the same love I gave to my little bro, to all dogs! Even though I don’t think I will get another dog, I still want that same love and joy I get with dogs! I am currently a nursing student looking for a good way to do what a love while earning some money. I have lecture on Wednesdays from 10:30am-1:30pm and clinicals from 2pm-11pm on Thursdays, other than that, my schedule is free. The house is usually never empty. I have a fenced yard built for a 100lb Weimaraner, so trust that it will hold your doggies. I always split meals 3 times a day, breakfast, lunch, dinner. Bathroom breaks happen always in the morning and before bed. More bathroom breaks can happen as needed. Dog walking usually happens in the mornings when before it gets hot. Playtime happens when requested by the doggies. Treats are available for good pups as needed.

Sitter Profile Image: Paula S.
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Paula S.
from
$20
per visit
5.0 out of 5 stars
21 reviews
7 repeat clients
15 years of experience
East Granby, CT, 06026

About: My career training makes me hyper aware of my clients needs whether they be human or animal. I can meet them where they are physically and mentally and cater to their needs. My work is flexible so my schedule can fit your pet's routine. I typically do my workout in the early morning which leaves the remainder of the dedicated to your pet's priorities. When I'm with your pet/s they are my priority whether it's feeding, walking, playing or just cuddling. I love animals but can't have them because of my husband's health issues. Yours is the best I can do.

Sitter Profile Image: Chelsea W.
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Chelsea W.
from
$20
per visit
5.0 out of 5 stars
5 reviews
4 years of experience
Bloomfield, CT, 06002

About: Hi, I am a work from home college student, I have been pet sitting for over 4 years and I have a loving toy cockapoo of my own. I have a large fenced in yard along with plenty of indoor space for cuddles, lounging, and running around. I follow pet parents routine for walk/eating allowing with optional photos/videos. I look forward to hosting your pet where dogs become family I work from home part time so I am always here with a flexible schedule to do walks, take breaks, and keep an eye on our furry friends! I have a large fenced in yard, my care depends on the pets needs, so weather they like long walks, cuddles, lounging on couch or deck, there needs will be catered to and pets will be well taken care of:)

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The median cost per visit for pet sitting in Windsor is $22

Pet parents share their Rover experiences - Windsor

1 / 1
5.0 out of 5 stars

Berkley was absolutely wonderful with my dog! She was extremely communicative, followed all of my instructions perfectly. I really appreciated all of the photos she sent—they made me feel so comfortable knowing my pup was in good hands. Berkley was reliable, caring, and clearly loves what she does. I would absolutely recommend her and will definitely be booking with her again!

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Elicea N.
Drop-In Visits
5.0 out of 5 stars

Jalah was wonderful with our pets. She took care of our chickens, ducks as well as our indoor cats and our dog for one day. She sent me daily updates and went above and beyond for my babies. Will definitely be booking her again. Thank you!!

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Jessica & Christopher F.
Drop-In Visits
5.0 out of 5 stars

Ashley was wonderful with our shy cat, it was nice knowing someone was there to check in on her while we were away.

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Christina B.
Drop-In Visits
4.0 out of 5 stars

Maegan was very attentive to my pups while I was gone and ensured they were happy, fed, and cared for. She kept in touch and made sure I was kept informed throughout. I would definitely hire her again!

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Shaina S.
Drop-In Visits
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Sitters in Windsor average 5
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 $24.52 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 2,228 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
  • 96% can help with giving oral medications or injections
  • 97% 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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