Dog Sitting in Cheshire

Book a Cheshire dog sitter to watch your dog in your sitter’s home or yours.

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Top rated Cheshire dog 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: Abigail P.
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Abigail P.
from
$20
per visit
4.9 out of 5 stars
15 reviews
4 repeat clients
2 years of experience
Wallingford, CT, 06492

About: I worked for The FurKid company in New York City. There, I walked dogs, as well as provided overnight care for dogs and cats, which includes administering medication to the animals. I'm a teacher, so I am mostly available outside of the 7:30PM to 3:30PM window. I pour a lot of love into the animals I care for, no matter how much time I have with them! I have no pets of my own, so will be able to put all of my energy into yours! I unfortunately don't have a yard, but there is plenty of green space and a dog park in my apartment complex.

Sitter Profile Image: Nicole G.
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Nicole G.
from
$20
per visit
5.0 out of 5 stars
8 reviews
1 repeat client
20 years of experience
Cheshire, CT, 06410

Nicole saved my butt with a last minute notice of needing someone to come let my dog out.. She had never even met my baby who tends to be very skittish around new people for a few seconds.. but she handled it like a pro and we came home to a content happy dog,so she must have been good to him!!! she even sent me an adorable photo.. she kept me informed.. she asked all the right questions.. I couldn't recommend her more! she was great..

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Lisa B.
Sitter Profile Image: Charlotte D.
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Charlotte D.
from
$20
per visit
10 years of experience
Hamden, CT, 06518

About: I've grown up surrounded by all sorts of animals and as soon as I could drive myself around I knew what I wanted to do. Without using a service I've dog-sat for over five families and have cat-sat for three. I'm very familiar with older animals as well as puppies and am determined to ensure that every animal I see feels loved. I'm currently a senior in high school and a varsity athlete. I, unfortunately, cannot see any animals during the week before 5:30 pm, but am willing to see them very late at night and at any time during the weekend. I have a fenced yard with two labradors and three cats, one indoor two outdoor. Also have several crates and beds. Always willing to take care of another furbaby.

Sitter Profile Image: Kate H.
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Kate H.
from
$25
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
10 years of experience
Wallingford, CT, 06492

Kate was absolutely amazing and really professional. I did not have any issues, even with my dog being a bit crazy at times. I would 100% recommend

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Andrew M.
Sitter Profile Image: Sara S.
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Sara S.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
38 reviews
12 repeat clients
10 years of experience
Wallingford, CT, 06492

After meeting Sara we felt extremely comfortable having her drop in with our guy. She is kind, asked lots of questions and confirmed the appointment ahead of time. The day of she arrived on time and sent lots of pictures- our guy loved her so much he let her rub his belly! We highly recommend Sara!

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Lisa B.
Sitter Profile Image: Christopher C.
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Christopher C.
from
$40
per visit
5.0 out of 5 stars
38 reviews
11 repeat clients
15 years of experience
Chesire, CT, 06410

Christopher was great. He arrived on time, played with our playful dog, and let our neurotic little one do his own thing. Highly recommended to sit for your pups!

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Mike P.
Sitter Profile Image: Sandra D.
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Sandra D.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
21 reviews
15 repeat clients
15 years of experience
North Haven, CT, 06473

Sandy is terrific! My dog Mika took to her right away at their Meet & Greet and was happy to see her when she arrived to walk and feed her a couple of days later. She communicates promptly which I really appreciate. I'll definitely be hiring Sandy again.

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Holly L.
Sitter Profile Image: Morgan K.
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Morgan K.
from
$25
per visit
5.0 out of 5 stars
31 reviews
3 repeat clients
5 years of experience
Waterbury, CT, 06706

Morgan was great with my shy cat! She helped me out last minute and came early morning for a meet & greet the day of the visit. I really appreciated her flexibility and calm energy. Will definitely book with Morgan again!

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Brittney P.
Sitter Profile Image: Francesca E.
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Francesca E.
from
$25
per visit
8 years of experience
Cheshire, CT, 06410

About: Whether your pup needs a midday walk to burn off energy, a friendly drop-in while you're at work, or a comfortable home-away-from-home for boarding, I treat every dog like my own. I'm patient, reliable, and attentive to each dog's unique needs — from high-energy pups to those who need a little extra TLC. Your dog's safety, happiness, and comfort are always my top priority. I'd love to meet your furry family member! I have flexible availability during the week & weekends. Available mornings, midday, and evenings on weekdays, and most weekends! Also available for boarding in my home. I will work with you to provide whatever care you need for your pet and will ensure to leave everything as I found it if visiting your home.

Sitter Profile Image: Tatum D.
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Tatum D.
from
$17
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
10 years of experience
Meriden, CT, 06451

Tatum was soooo great with my quirky dog! She totally went above and beyond to make sure my nervous nelly was comfortable enough to eat and do her business. She also kept me updated on everything that was going on with my pup and my kitty. I’ll definitely work with Tatum again!

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Alexis G.
Sitter Profile Image: Sara R.
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Sara R.
from
$19
per visit
5.0 out of 5 stars
11 reviews
3 repeat clients
10 years of experience
Prospect, CT, 06712

Sara is amazing. She followed my instructions and she kept in touch with me on how our old lady was doing. She used good judgment with regard to the poor air quality and heat by limiting the time our dog was out. She paid attention to our dog as well. I desperately wish she lived closer to us and am so thankful that she was able to come to our home. I highly recommend her and believe anyone who gets to have her take care of their pets is very lucky. She also has excellent work ethics.

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D G.
Sitter Profile Image: Whitnee M.
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Whitnee M.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
26 reviews
7 repeat clients
14 years of experience
Meriden, CT, 06451

Whitnee was fantastic with Echo! She was willing and ready to help me extremely last minute and took the extra time to make sure Echo had the care he needed! Thanks so much Whitnee!

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Isabelle M.
Sitter Profile Image: Brooke P.
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Brooke P.
from
$20
per visit
15 years of experience
Cheshire, CT, 06410

About: I'm a huuuge pet lover! I have two cats of my own, routinely watch/walk my brother's dogs, and also volunteer at my local cat shelter every weekend. Cleaning up litter boxes, poop, hairballs, and puke are second nature to me haha! I also took care of my senior cat who lived to 23 years, so senior pets have a very special place in my heart. Rest assured your pet will be in great hands with me. :) I am remote 3x/week so my schedule is very flexible. I am often free any time of day (besides tuesdays & wednesdays) from 7am to overnights if needed. I'm flexible to all scheduling - just let me know! I do dog walks, dog feedings, cat feedings, and cat walks (if you are interested!) :) I will keep all pets company if youre just at work for the day or need a late-night stay for a date-night.

Sitter Profile Image: KELLY G.
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KELLY G.
from
$25
per visit
1 repeat client
30 years of experience
Meriden, CT, 06450

About: I try to take parts of Cesar Milan's strategy with dogs specifically. Trying to not reward bad behavior. Making sure a pet can respect my boundaries. I work flexible hours as an independent contractor so I make my own schedule. I am building my pet care business so I am signing up for a drone pilots license for pet recovery. I am also working on upgrading my vehicle to a minivan. I am offering pet sitting in your home until that can change to my home. I am needing different things done to my home before I can bring pets to my house.

Sitter Profile Image: Deborah W.
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Deborah W.
from
$20
per visit
5.0 out of 5 stars
5 reviews
10 years of experience
Cheshire, CT, 06410

Deb was great with my energetic pup! She was very communicative throughout the whole process and provided updates during drop-in visits. I would highly recommend her and will definitely a repeat customer in the future!

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Jessica H.
Sitter Profile Image: Cassiopeia A.
Verified Enhanced Background Check
Cassiopeia A.
from
$25
per visit
5.0 out of 5 stars
1 review
10 years of experience
Wallingford, CT, 06492

About: Over the years I have provided dog walking services as well as drop-in & overnight care for dogs, cats, guinea pigs, rabbits, birds, fish, etc. I grew up with dogs, kept guinea pigs for the last 10 years, and now have two kitties (Callisto & Io). I've always loved animals and would love to care for yours! I currently work 4 days per week (between Monday & Friday) typically between 10:30am - 6:30pm. I am available before & after work as well as on weekends! I cannot care for pets in my home as I have my own kitties. In your home, I will follow all instructions given & use my best judgement otherwise.

Sitter Profile Image: Tom F.
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Tom F.
from
$25
per visit
5.0 out of 5 stars
9 reviews
3 repeat clients
30 years of experience
Cheshire, CT, 06410

Tom and his oldest daughter took excellent care of our 2 cats when we were out of town! They quickly became comfortable with them which is a testament to how much they love animals. We will certainly be using them again in the future!

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Marc M.
Sitter Profile Image: Camryn K.
Verified Enhanced Background Check
Camryn K.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
11 reviews
3 repeat clients
12 years of experience
Wallingford, CT, 06492

Camryn was great. She handled our three dogs very well and kept us very well-informed, and was able to stop in on very short notice. The dogs loved her, and even one of our skittish cats came to say hello. Thanks, Camryn!

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Zack M.
Sitter Profile Image: Nicole C.
Verified Enhanced Background Check
Nicole C.
from
$16
per visit
3 years of experience
Cheshire, CT, 06410

About: I received my bachelor's degree in animal science in 2025 and now attend vet school Puerto Rico. I just completed my first year! I have a year's worth of large animal experience on a dairy farm, and have always worked and lived with cats. I also have pet sat for a few years, and care for cats and dogs on and off campus while at school. When I am responsible for the care of animals, it is my utmost priority. Arriving on time with a positive attitude, and staying until the work is complete, is imperative in maintaining a respectful routine for animal care. I like to try to see the world from my animal's perspective. With that, I would accommodate to the specific animal and their needs. I also will follow direct instructions explicitly, and respect the decisions of the pet owners.

Sitter Profile Image: Lydia K.
Verified Enhanced Background Check
Lydia K.
from
$20
per visit
5.0 out of 5 stars
8 reviews
2 repeat clients
8 years of experience
Wallingford, CT, 06492

Lydia took great care of my 2 young cats, I couldn’t be happier. This was my first time using Rover and I won’t hesitate to use in the future. 😊

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Catherine D.
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Over 61
pet parents in Cheshire have booked dog sitting

Cheshire dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Dave is the best! My dog is always so happy to see Dave when he comes over. I really appreciate and enjoy his notes and comments after his drop ins and walks. I’d give him 10 stars if I could.

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Jaclyn W.
Drop-In Visits
5.0 out of 5 stars

Katherine is incredible. She is extremely flexible and reliable. My 3 dogs have different personalities and she was able to connect with each of them. She made sure I home from my trip and the dogs were being taken care of. I highly recommend her.

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

Samantha was fantastic! I would have her watch my dog and cats again in a heartbeat. She’s great with animals and a very sweet person too.

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Adrienne D.
Drop-In Visits
5.0 out of 5 stars

We had a great experience having Corbin watch our pets while we were away. We have multiple pets with varying feeding schedules and medications, and he handled everything so well, including watering my porch plants, such a relief! Very responsible and we can tell our dog had a great time with her new friend. Will definitely be using him again in the future.

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

Tom and Family are flexible, caring and genuinely wonderful humans who take the care of your Pet family seriously, with kindness and good humor. Wonderful, wonderful people.

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Regina G.
Drop-In Visits
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Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs 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!

The median cost per night for dog sitting in Cheshire is $25

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 dog sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.

Sitters in Cheshire average 5
repeat dog sitting clients

Dog Sitting FAQs

Frequently asked questions about Rover

Dog sitters on Rover are free to set their rates. The median cost to hire a dog sitter in Cheshire on Rover as of Jun 2026 was about $25 per night, after factoring in Rover’s service fees. A dog sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.

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

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

As of Jun 2026, there are 2,910 dog sitters in Cheshire. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, 88% of Cheshire dog sitters respond in under an hour.

Dog sitters in Cheshire have an average of 16 years of experience. Dog sitters with repeat customers have an average of 5 repeat clients. Experience can vary from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Cheshire.

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

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

There are 2,910 dog sitters in Cheshire on Rover, so you’re sure to find the perfect match for your dog! In Cheshire, 96% of dog sitters offer daily exercise, 97% offer medication administration, and 95% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass background checks for you and your dog’s safety.

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

Note: If your dog 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 dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.