Dog Sitting Cheshire

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

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Over 38
pet parents in Cheshire have booked dog sitting

Cheshire, Find top rated dog 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: Taylor M.
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Taylor M.
from
$18
per visit
1 repeat client
23 years of experience
Prospect, CT, 06712

About: I have a great, rambunctious 6-year-old Golden Retriever named Cobie, and previously had another wonderful, loving Golden Retriever named Max, who we cared for well into his old age--17! I have taken care of dogs for friends and family all throughout my life, and always shower them with all the love in the world! I am currently in graduate school, but I am available for late afternoons or evenings and nights during the week, and anytime during the weekend! I always ensure safety of the dog and the home, whether that be crates, blocking off parts of the house, and following set rules and routines. Just as important is love and gentleness, doing my best to build a dog's trust.

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

“This was my third time booking Sara. My cats love her and I love not having to worry about them when I am away. They’re always in good hands with Sara! Thanks again Sara for taking such good care of them! 🐱😻🐱”

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Marisa C.
Sitter Profile Image: Mckenzie P.
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Mckenzie P.
from
$18
per visit
5.0 out of 5 stars
• 12 reviews
3 repeat clients
4 years of experience
Southington, CT, 06479

“We had such a great experience with Mckenzie! From the very beginning, she was communicative, reliable, and clearly loves what she does. It gave us so much peace of mind knowing our puppy was in good hands. We also loved the photo updates. We came home to a relaxed, happy puppy, and that says everything. We would absolutely book with her again and highly recommend her to anyone looking for a trustworthy and caring sitter!”

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Courtney L.
Sitter Profile Image: Alex T.
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Alex T.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 70 reviews
25 repeat clients
4 years of experience
North Haven, CT, 06473

“Brinkley had such a great time with Alex. I could tell they played a lot of fetch because Brinkley was sleeping the rest of the day until I came home from work. She made a point to try and meet Brinkley before coming to take care of her to make sure she knew what my girl needed.”

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Kelsey W.
Sitter Profile Image: Jasmine C.
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Jasmine C.
from
$13
per visit
5.0 out of 5 stars
• 5 reviews
3 repeat clients
5 years of experience
Hamden, CT, 06518

“Jasmine was great and quick to respond to questions and provided detailed visit notes each time! My dog was in such good hands with her check ins.”

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Kriza S.
Sitter Profile Image: Katherine W.
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Katherine W.
from
$25
per visit
5.0 out of 5 stars
• 1 review
12 years of experience
Cheshire, CT, 06410

About: I was the primary caretaker of my family dog for about 10 years, while I was living at home, and I was a part-time dog sitter in college. I currently have a flexible schedule, so I’ll have plenty of time to tend to and play with your furry babies. I can make anytime during the week work! :) In someone else’s home I treat both the pet and the house with respect. I ensure I know exactly what the pet is used to: whether they sleep on the bed, use a crate, how they interact with other pets or children. I secure the perimeter (doors closed, yard gate locked), I follow any medication or behaviour instructions closely, and I keep a log of walks, meals, playtime, and potty breaks. At night I do a last check: water bowl full, lights are safe, any doors/windows secured, pet comfortable in its space. I aim to leave the home just as I found it, if not neater.

Sitter Profile Image: Kailah J.
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Kailah J.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
• 11 reviews
6 repeat clients
3 years of experience
Waterbury, CT, 06706

“Kailah has been great with my dogs! I have 2 rescues who are super nervous around new people. This was our 3rd time booking with Kailah, she has been super patient and they are starting to warm up to her. I would recommend Kailah and will definitely be using her services again.”

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Molly R.
Sitter Profile Image: Lindsay & Lisa K.
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Lindsay & Lisa K.
from
$10
per visit
10 years of experience
Southington, CT, 06479

About: I’ve taken care of dogs my whole life from as big to German shepherds to as small as mini dachshund. I currently have a 15 week old golden so very used to the puppy stage. I currently work at home so I’m able to come during the week at the times u need to take care of ur fur baby. I have a fenced in yard along with a 16 year old golden retriever maisy. I live with my mother who is the biggest dog lover as well. I grew up with 2 German shepherd bd a mini dachshund so I’m good with all Breeds and sizes. We also have a crate at our home if u need boarding

Sitter Profile Image: Roderick M.
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Roderick M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 14 reviews
4 repeat clients
8 years of experience
Bristol, CT, 06010

“First time having him walk oaks....he's amazing definitely rebooting he's kind patient deals w my foxhound bordercollies quirks .....best walks ever for ms oaks ....she loves his visit...can't wait to rebook”

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Sheryl R.
Sitter Profile Image: Michael D.
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Michael D.
Star Sitter
from
$25
per visit
4.9 out of 5 stars
• 26 reviews
11 repeat clients
20 years of experience
Southington, CT, 06489

“Michael was great. Jax loved him. Michael went above and beyond to make sure Jax got the attention he needed. And we always got good feedback from each visit.”

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David S.
Sitter Profile Image: Carly N.
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Carly N.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 25 reviews
16 repeat clients
27 years of experience
Hamden, CT, 06514

“Carly was wonderful to work with! She was a great communicator and asked thoughtful questions during our meet and greet. She was great with our dog!”

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Michelle P.
Sitter Profile Image: Rosa D.
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Rosa D.
from
$20
per visit
5.0 out of 5 stars
• 12 reviews
5 repeat clients
10 years of experience
Prospect, CT, 06712

“The best!”

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Nathan M.
Sitter Profile Image: Kelly R.
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Kelly R.
from
$25
per visit
5.0 out of 5 stars
• 4 reviews
2 repeat clients
12 years of experience
Meriden, CT, 06451

About: I’ve worked at a boarding kennel, dog sat, and taken care of many animals big and small throughout the years. I’m comfortable with dogs, cats, goats, chickens and horses too. I am in real estate and have flexible hours throughout the week. I am home most of the time taking care of the farm, animals and my sons! I have seven acres surrounded my trees and hills. I have two pups to keep your pal company (but can separate any if some quiet time needed)! We spend lots of time outside playing! We recently added a fenced in play yard for off leash play.

Sitter Profile Image: Erin O.
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Erin O.
from
$17
per visit
15 years of experience
Southington, CT, 06489

About: I’ve had pets my entire life and have always loved caring for animals. I have experience walking dogs, dog-sitting, and house-sitting for pets, and I’m comfortable caring for pets with different personalities, energy levels, and routines. I’m responsible, dependable, and attentive to each pet’s individual needs. I treat every pet as if they were my own and always prioritize their safety and happiness! I’m currently in an accelerated nursing program, so I have a structured but flexible schedule. I have two in-person classes for 2 hours each on Mondays and Wednesdays, and clinicals on Thursdays. I’m generally available after 3 PM on Thursdays, and I’m fully available Tuesdays, Fridays, Saturdays, and Sundays. When caring for pets in a client’s home, I make it a priority to follow their usual routine and instructions closely. I understand how important it is to feel comfortable trusting someone with both your pet and your home, so I am respectful and thoughtful of their wishes. I always make sure pets are safe, comfortable, and well cared for, while keeping their environment clean and secure. I’m also happy to provide updates and photos so pet parents can have peace of mind while they’re away!

Sitter Profile Image: Jessica S.
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Jessica S.
from
$20
per visit
15 years of experience
North Haven, CT, 06473

About: I’ve grown up around dogs my entire life and have experience caring for dogs of all different sizes, breeds, and personalities. I’ve always loved spending time with dogs and making sure they feel comfortable, happy, and cared for. I also have experience caring for dogs while babysitting for families, including feeding them, taking them outside, playing with them, and giving them plenty of attention. I’m responsible, dependable, and would love the opportunity to help care for your dog like they’re my own! I’m currently a graduate student, so I have a pretty flexible schedule with plenty of openings between my classes. This gives me a lot of availability throughout the week, and I’m happy to work around your schedule and your pet’s normal routine! I always want pets to feel safe and comfortable around me. I allow each animal to move at their own pace when getting to know me and give them the time and space they need to build trust. I never force interactions and will always respect your pet’s boundaries while making sure they feel cared for and loved.

Sitter Profile Image: Jordan S.
Verified Background Check
Jordan S.
from
$20
per visit
5.0 out of 5 stars
• 32 reviews
10 repeat clients
5 years of experience
Hamden, CT, 06514

“Jordan did a really nice job looking after my cats! I appreciated how communicative she was and her adorable pictures of them while I was away.”

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Nicole C.
Sitter Profile Image: Sadie R.
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Sadie R.
from
$30
per visit
5.0 out of 5 stars
• 11 reviews
4 repeat clients
15 years of experience
Plantsvile, CT, 06479

“Cesar had a great visit with Sadie, Sadie was very informative asked questions regarding Cesar very professional looking forward to future visits and overnight stays with our Cesar”

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Aida R.
Sitter Profile Image: Kenzie W.
Verified Background Check
Kenzie W.
from
$30
per visit
4.9 out of 5 stars
• 27 reviews
13 repeat clients
20 years of experience
Wallingford, CT, 06492

“Kenzie is fabulous. Her love and ease with animals was evident at our first meet. Kenzie is flexible and dependable. She went above and beyond to check in on our cat while we were on vacation who wasn’t feeling well. We felt such a sense of relief knowing our animals were in safe hands while we were away. Highly recommend.”

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Shannon R.
Sitter Profile Image: Camden W.
Verified Enhanced Background Check
Camden W.
from
$30
per visit
10 years of experience
Cheshire, CT, 06410

About: I’ve had pets and been a pet sitter for 10+ years. I love animals and want to help out my community! Getting paid to play with dogs and cats?? Sign me up! ;-) I work full time from home so I have flexibility to care for your pets any time of the day, just book in advance for extra flexibility! I can provide drop-ins, overnight stays and walks! As a dog and cat mom myself, I make sure to meet the pet where they are with lots of love!

Sitter Profile Image: Brooke P.
Verified Background Check
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.

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

Dog parents share their Rover experiences - Cheshire

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5.0 out of 5 stars

Another great visit from Lori! My dogs love her and that’s all that matters to me, BUT Lori is also really great and so easy to work with! She has great communication and not only made sure she knew every detail about my dogs, but also took time to make sure she acquainted herself with our house so she’d leave the house and dogs secure after her visit. I really appreciated that.

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Jana B.
Drop-In Visits
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
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Meet local sitters who will treat your dogs like family

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Popular requests for dog sitting - Cheshire

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Sitters in Cheshire average 5
repeat dog sitting clients

FAQs for Dog Sitting - Cheshire

Frequently asked questions about Rover

The average cost of Dog Sitting in Cheshire on Rover is $19 per visit as of October 2026. Most bookings cost between $16 and $33 per visit. sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 2,806 sitters on Rover offering Dog Sitting across Cheshire. Enter your ZIP code to see which available sitters are closest to your home.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Cheshire choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

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.

A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet .

While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.

To find sitters in Cheshire with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.

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

  • 95% of sitters can help with special care needs
  • 97% can help with giving oral medications or injections
  • 96% 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.

sitters on Rover set their own cancellation policy , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.

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