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

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Sitter Profile Image: Laura L.
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Laura L.
from
$22
per visit
5.0 out of 5 stars
• 8 reviews
1 repeat client
25 years of experience
Meriden, CT, 06451

About: I've had pets for 50 years. Have dogs and cats. Work with TNR in my community. Care for feral colonies. Can administrator medication, IV fluids and sub q injections. I can handle special diets. Recently completed an Approved Vet Tech Assistant program and have passed the National Exam. I completed 100 hours at a local vet hospital as well. I'm currently working a flexible part time job. I do not have children at home or other responsibilities. I am available holidays, evenings and weekends. I can administer medications, I can walk dogs, can handle special diets, can handle multiple pets (I currently have a client with 10 special needs cats).

Sitter Profile Image: Mark B.
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Mark B.
from
$50
per visit
5.0 out of 5 stars
• 747 reviews
355 repeat clients
20 years of experience
Wallingford, CT, 06492

“We were very pleased with Mark’s services. He took really good care of Abby and Nicco. He communicated with us frequently and sent us pictures every day we were away. I could tell that my pups were content, because when we came back they were happy, full of energy and their normal self (not the same response from when we left them with another sitter, horrible experience ?). We will definitely stay in touch with Mark.”

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Melissa M.
Sitter Profile Image: Ashley G.
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Ashley G.
from
$30
per visit
4.9 out of 5 stars
• 81 reviews
34 repeat clients
2 years of experience
Southington, CT, 06489

“Ashley has been a god send to our family (and our pup). She has helped our family out last minute on many occasions, and when we are both at work my mind is at peace knowing Ashley is scheduled to care for our dog. She is reliable and I know my dog is in good hands when she is sitting her. I can’t say thank you enough for her help.”

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Kelsey A.
Sitter Profile Image: Ashley B.
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Ashley B.
from
$22
per visit
12 years of experience
Wallingford, CT, 06492

About: I’ve been taking care of dogs ever since I was 12 years own and at the age of 20, 2 years ago I bought my own first dog. I’ve spent the first few months of her life training her and she’s the sweetest golden retriever I’ve ever had I’m currently working full time from 8:30am-5:30pm but get 2 breaks a day where I can stop by closer to 4pm. I do have weekends and nights completely free. That’s when I have the most time to play and take care of your pets! I have a fenced in yard for your pets and can easily crate pets if necessary. There is always love and room for more pets!

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: Ola K.
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Ola K.
from
$30
per visit
4.8 out of 5 stars
• 7 reviews
1 repeat client
20 years of experience
Middlefield, CT, 06455

About: I've had pets since a young age from lizards, cats, dogs, hamsters, fish, turtles, guinea pigs and birds. I have a small dog of my own so I know I can give your pets lots the love and attention too whether they have fur, scales, or feathers! I work from home so all pets get get a lot of attention during the day. For dogs staying in my home, they get 3 walks a day in the morning, during my lunch break, and in the evening. I work from home so all pets get a lot of attention during the day. I love to spend my time after work going on walks and would love a buddy(s) to come with me! I am available from dog walking or in home visits after 5:15pm during the week and anytime on weekends. I think the best way to care for a pet is do exactly what they're comfortable with. I intend to have very open communication with pet parents to understand the likes, dislikes and behaviors of their fur-babies to make sure that they feel safe and comfortable. I do have a dog of my own so I also want to make sure all your pets get along with my Jax, who loves other animals.

Sitter Profile Image: Theresa M.
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Theresa M.
from
$23
per visit
5.0 out of 5 stars
• 7 reviews
1 repeat client
3 years of experience
Southington, CT, 06489

“Theresa took excellent care of our cats while we were away. She followed instructions exactly and was very responsive to messages. Most importantly the cats liked her! Would absolutely recommend her, and will be hiring Theresa again for our next trip”

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Carol F.
Sitter Profile Image: Kyara F.
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Kyara F.
from
$25
per visit
5.0 out of 5 stars
• 1 review
3 years of experience
Waterbury, CT, 06704

About: As someone who knows that your pet is a part of your family, you can trust that I will do my absolute best to take care of them. I have been a pet sitter for 4 years, providing exceptional care to the pets of neighbors, family, friends and clients. I have experience caring for pets with special needs, dietary restrictions, and medication. I’m currently working full time, but I’m available for overnights with any pet! I’m okay with traveling the distance to your house to watch your pet as well as house sit if needed! I understand that animals feel most comfortable around familiar surroundings, and wouldn’t want to displace them. I’m very flexible, just let me know when I’d be needed. The environment will be your own home. Your pet will not feel displaced, and will remain comfortable in his or her own bed. I understand that familiarity is key when owners are away.

Sitter Profile Image: Elizabeth L.
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Elizabeth L.
from
$30
per visit
5.0 out of 5 stars
• 24 reviews
4 repeat clients
3 years of experience
Naugatuck, CT, 06770

“Elizabeth was professional and easy to work with. She went above and beyond at taking care of our three large dogs while we were away. Would definitely recommend!”

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Laura B.
Sitter Profile Image: Elizabeth F.
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Elizabeth F.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
• 5 reviews
2 repeat clients
10 years of experience
Newington, CT, 06111

About: Hi there! My name is Ellie, and I’m a passionate animal lover with over a decade of hands-on experience caring for dogs of all breeds, sizes, and personalities. I have pups of my own, so I know how much trust it takes to let someone else care for your furry family member — and I treat every pet I meet with the same love, attention, and respect I give my own. Whether your dog needs a fun walk to burn off energy, a drop-in to check on meals and snuggles, or full-on overnight care, I’ve got you covered. I’m reliable, patient, and fully committed to making sure your pet feels safe, happy, and loved while you’re away. I can’t wait to meet your fur baby and give them the care they deserve! I currently work full-time during the day, but pet care is truly a passion of mine and a fulfilling part of my daily routine. I’m available for check-ins and walks in the early mornings before work and in the evenings after I get home. In some cases, I’m also able to swing by during my lunch break for a quick visit, depending on location and timing. I also offer overnight stays, which allows me to spend quality, uninterrupted time with your pet — perfect for dogs who need extra comfort or company while you’re away. While my weekday daytime availability is limited, I’m dependable, communicative, and always make sure your pet gets the attention and care they deserve when I’m with them! When your pet is in my care, their well-being is my top priority. I understand that every animal has their own unique needs, routines, and personalities — and I take the time to get to know them so I can provide care that makes them feel safe, seen, and loved. You can trust that I’ll treat your pet like one of my own, with patience, affection, and respect. I’m mindful, responsible, and always keep safety at the forefront — whether that’s making sure harnesses are secure, sticking to feeding instructions, or giving them their favorite toy at just the right moment. I believe animals know when someone truly cares for them — and I make it my mission to create a peaceful, loving environment where your pet can feel completely at ease while you’re away.

Sitter Profile Image: Thea J.
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Thea J.
from
$17
per visit
5.0 out of 5 stars
• 15 reviews
2 repeat clients
5 years of experience
Wolcott, CT, 06716

“Amazing experience! Kept in contact after each visit. Very communicative and kind as this was our first sitter for our pup. 100/10 experience :)”

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Kylie H.
Sitter Profile Image: Denise C.
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Denise C.
from
$20
per visit
32 years of experience
North Haven, CT, 06473

About: My love affair with animals started at 8 years old. Fast forward many years later and my passion for animals has only grown. I have 3 fur babies of my own and plan on adding more someday! I am available on weekends but also willing to make arrangements if needed for longer periods. Simply reach out and advise me of your needs. I will try my best to accommodate. Pups are a part of our family so their happiness and safety are mist important to me. Finding the best and safest way to accommodate our fur babies is paramount and varies from owner to owner.

Sitter Profile Image: Joy C.
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Joy C.
from
$13
per visit
5.0 out of 5 stars
• 2 reviews
30 years of experience
Seymour, CT, 06483

About: I have grown up with large dogs (Dobermans, Pitties, Mastiffs) my entire life. I have been rescuing Pitties for over 20yrs and am currently on my fourth rescue. I am experienced with medication administration, special needs and, all ages of dogs from newborn to senior. I have an hour lunch break and, am free after 3pm daily and, all day every other wknd! I care for my 3 pets and can't wait to get home and see them! I work 7-3 most days but, my dog is yard trained so, can be let out multiple times when I am not at home. Once I do get home, we head out for a walk and then, its dinner time! All of my animals are allowed on my furniture and, choose who's bed they sleep in each night!

Sitter Profile Image: Ana V.
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Ana V.
from
$46
per visit
5.0 out of 5 stars
• 2 reviews
17 years of experience
Hamden, CT, 06518

About: I am someone who truly sits down and connects and listens to each animal and approach things wholeheartedly with the mindset as each animal is just as special as a human being; mentally and physically. I’m patient and will let your baby shine on their intelligence with basic commands and pad training if need. Give adequate spacing when walking outside around others. I have cared for senior pets before ensuring ultimate care and compassion with each moment. Ultimately giving essential careful love, vocal understanding and letting them thrive with every special presence. I used to live on a farm with bigger dogs so I give a good three whole second rule; if they are the type to pull on leashes, they’ll have that time to truly explore before we move on. I’m pretty much flexible and am the type to be prompt and communicate swiftly of any notifications. I don't mind the CT weather and distances.😊 I always plan properly ahead plus faith with my intuition.💠 Avalnt.3@ gmail . Com is where you can reach for more real time updates of my schedule. I am very structural, organized and will keep it to what the pet parents preferences are. I prefer visual instructions if things are deemed tedious or complex. I work remotely so I’ll have some time to serenade your pet if they enjoy musicals and or theatrical expressions. Overall, I’m open with a lot, including many species of pets and will stick to your pet’s routine. I’m a quick learner and will ask questions to ensure your pet is happy and safe!

Sitter Profile Image: Jaylese H.
Verified Enhanced Background Check
Jaylese H.
from
$25
per visit
5.0 out of 5 stars
• 33 reviews
11 repeat clients
6 years of experience
Plymouth, CT, 06786

About: I've been taking care of my own pets for 6+ years. I make sure pets feel loved and well-cared for, whether it's playtime, feeding, or just giving them some extra snuggles. I understand that each pet has unique needs and preferences, so I adapt my approach to suit their individual personalities. Devoted and loving pet caretaker available around the clock. With a very flexible schedule, I can provide frequent walks, playtime, and feeding to keep your pets happy and healthy. I have a yard for your pet to play in with supervision. I have a small dog and cat that are friendly, But they can be moved to another part of the house if you prefer.

Sitter Profile Image: Kaitlin R.
Verified Enhanced Background Check
Kaitlin R.
from
$25
per visit
5.0 out of 5 stars
• 8 reviews
2 repeat clients
11 years of experience
Hamden, CT, 06517

“Very responsive and great care for our cat!”

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Emily B.
Sitter Profile Image: Dave F.
Verified Background Check
Dave F.
from
$16
per visit
5.0 out of 5 stars
• 14 reviews
6 repeat clients
20 years of experience
Prospect Hill, New Haven, CT, 06511

“Dave took care our beautiful cat! Our cat not only had ots of fun with Dave, but he also brushed his teeth and his fur too! Dave also noticed that our cat was lonely and spent extra time with him! Highly recommend Dave!”

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Wilbert T.
Sitter Profile Image: Conor M.
Verified Enhanced Background Check
Conor M.
from
$18
per visit
5.0 out of 5 stars
• 7 reviews
1 repeat client
8 years of experience
East Rock, New Haven, CT, 06511

About: Life time owner of cats and dogs throughout his life. Has been watching friend and family pets for several years. Experienced with cats and small to medium sized dogs. I currently work remotely Mon/Weds/Fri. I’m in office on Tues/Thurs but am flexible. Every Wednesday I will be unavailable from 7:30pm to 10 pm. I will meet with potential clients face to face prior to accepting any request. Firstly, to go over any specific needs or questions of your pet and second, to get to know you as an owner.

Sitter Profile Image: Hailey Z.
Verified Enhanced Background Check
Hailey Z.
from
$45
per visit
4.5 out of 5 stars
• 9 reviews
4 repeat clients
19 years of experience
southington, CT, 06489

About: I have had dogs my whole life and they mean the world to me! I have cared for the pets of friends, family, and strangers and treat each and every one of them as if they were my own. I have experience caring for dogs of all ages from puppies to seniors, able to give most forms of medications, provide walks/exercise, and anything else your pet might need! I am currently a senior in college living at home and work part time on weekends. I am flexible with my schedule and am usually able to provide bathroom breaks every 4-8 hours. My family is also super helpful with the pets and can assist with boarding drop offs and pick ups if I am unavailable! I have a big backyard and 2 of my own very friendly dogs who love to make new friends. I take them for walks 3 times a day (morning afternoon and night) and hang out with them constantly. They are very well taken care of and your pet will be too!

Sitter Profile Image: Ewa J.
Verified Enhanced Background Check
Ewa J.
from
$15
per visit
5.0 out of 5 stars
• 1 review
10 years of experience
New Britain, CT, 06052

About: 🐾 Need a Pet Sitter? 🐾 Over 20 years of experience caring for pets – now with my son by my side! 🐶🐱 We love giving pets the attention, walks, and cuddles they deserve. ✔️ Walks ✔️ Weekends ✔️ Vacation care Because your pets deserve care that feels like family. ❤️ We live in New Britain,CT but we don't mind travelling long distances within the state. 🚗 📅 Message me to book! I’m currently looking for weekend/holiday pet sitting jobs if possible for extra income. I am flexible during the weekends and holidays. If it's an emergency I will try my best to be able to take care of pets during the weekdays. I would prefer to take care of pets at my clients home if possible. I would take care of the pets according to specific needs to the best of my ability.

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

Dog parents share their Rover experiences - Cheshire

1 / 1
5.0 out of 5 stars

Right from the start, Lori asks, listens and understands how to best care for your pet. She is very professional, punctual and overall a great fit for me with caring for my miniature dachshund! You can tell Lori genuinely loves pets and animals. I highly recommend her!

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Carol M.
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

Christine has done a great job taking care of our dog. She is a good communicator, punctual and reliable. I can tell she takes care of our dog like he is her own! She provided us with lots of updates and pictures from her drop in visits, which is much appreciated. If you are looking for pet care I would definitely recommend Christine!

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Desiree B.
Drop-In Visits
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  • 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?

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    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

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

How to book dog sitting

  1. 1. Search

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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 is $19 per visit as of October 2026. Most bookings cost between $16 and $32 per visit. On Rover, 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 2,783 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 .

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 , 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 .

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:

  • 90% of sitters can help with special care needs
  • 92% 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 , 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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