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: Delaney B.
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Delaney B.
from
$13
per visit
10 years of experience
Hamden, CT, 06518

About: I’ve been around dogs all my life, but started caring for them on my own since I was 10 years old. As I got older, I was around cats more and more, and now I have a great love for both pets!! My experience includes walks, potty breaks, playtime, overnighting with pets, senior care, and caring for high energy dogs. I often work on the weekends and Wednesday nights, but like to stay busy during the week. Staying busy mostly means being active and running errands. Pet care is a perfect opportunity for me to fill in the gaps! I will visit the pets as much as needed, feed them when advised to, pet them and play with them, and take them on nice, relaxing walks.

Sitter Profile Image: Stephanie S.
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Stephanie S.
from
$18
per visit
1 repeat client
10 years of experience
Hamden, CT, 06518

About: I've grown up with animals since I was born and have gained the largest appreciation for pets of all shapes and sizes. Besides this, I have watched numerous pets for friends, family, and neighbors and ensured all pet's needs were met. Whether this was special diets, long walks, hours of play time, I love spending any and all time with animals. I do work a full time job usually M/W/F/Sun from 4 until about 12:30pm. I am also a full time student working on getting her bachelors. I always make plenty of time for drop ins to care for pets. Saturdays are usually always free so I have the time to really care for your pets needs! I’m willing to discuss what availability you’re looking for. I am open to almost all special requests you might need for you pet! Whatever practices/care needs you are looking for, I am willing to adjust to.

Sitter Profile Image: Lauren G.
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Lauren G.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
• 3 reviews
3 repeat clients
28 years of experience
Berlin, CT, 06037

“Lauren is our go-to dog walker now! She’s reliable and timely, and cares for my elderly dog with all of her many medication needs. Lauren is awesome. Would highly recommend.”

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Renee T.
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: 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: 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: Justin H.
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Justin H.
from
$22
per visit
5.0 out of 5 stars
• 4 reviews
10 years of experience
Meriden, CT, 06450

About: Had a dog since I was a child, and have continued to have dogs my whole life. My current dog is 6 and great around children/other dogs (when she isn’t sunbathing). Currently job hunting so until that changes availability is relatively open. Early riser and love taking my dog on early morning walks in nice weather. A crate and in house fence are available, as well as sectioning off into separate rooms if needed. Plenty of beds and sleep/play space available.

Sitter Profile Image: Jen N.
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Jen N.
Star Sitter
from
$27
per visit
5.0 out of 5 stars
• 479 reviews
133 repeat clients
30 years of experience
Edgewood, New Haven, CT, 06511

“Jen is amazing. I could not ask for a better cat sitter. She really connected with my cat Bubba and spoiled him like her own and gave me a peace of mind while traveling. I’m so grateful I found her and will continue to request her services.”

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Joseph K.
Sitter Profile Image: James E.
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James E.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
• 45 reviews
10 repeat clients
40 years of experience
Bristol, CT, 06010

About: Welcome, y'all! I love watching dogs. We watch kitty cats too 😁. Cheapest rates around! Let me make it easier for you to celebrate your vacation and holidays! Let me sit for your pup. I...love... dogs! My parents were dog breeders for years. As a youngster, I was responsible for many of the chores. As an adult, I have always had pets. I know how important your dog is to you. Your dog is your 'baby'. We are definitely dog lovers in this house! Big dog specialist. I love the little dogs too, though! ☺️💪🎄🎁❤️‍🩹 I will treat your pup like my own. I am a teacher during the day. I'm usually home by 3. I'm home every afternoon and every night and every weekend. I do have flexibility in my work schedule should they need arise. I have a dog lead hooked up to the house and it goes all the way back to the maple tree on the back of the property. 20 ft in either direction gives Fido plenty of room to go to the bathroom. Otherwise, your pup is in the house with me and my family. I am offering dog boarding services. This is a friendly Christian home. Lots of love to share.

Sitter Profile Image: pauline g.
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pauline g.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
• 127 reviews
28 repeat clients
20 years of experience
East Rock, New Haven, CT, 06511

“Pauline was a great cat sitter! She sent frequent updates with detailed photographs, which gave me peace of mind that my elderly cat was happy and well cared for. I highly recommend Pauline to anyone looking for a reliable, caring pet sitter and will certainly book her services again in the future.”

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Avary T.
Sitter Profile Image: Danishka C.
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Danishka C.
from
$30
per visit
5 years of experience
Waterbury, CT, 06706

About: Hello! My name is Dani and i am 22 years old! im offering my pet sitting and dog walking services and more ! Your pet will be with someone who genuinely care about their happiness and well being and someone who loves dogs or cats 🐈🐕!! Little more about me i work at an animal care facility. i am very passionate about my work and with animals 🐕! Growing up with different types pets taught me how to care and love all animals different sizes and ages 🐈🐕‍🦺🦮! I also have experience with bathing / Brushing Nail clipping If you’re interested in those services as well . If you need Pet sitting/house sitting please let me know and we could arrange times and days that work! ☺️. i could do late afternoon/evening walks and pet sitting or sometimes early/mid morning dog walking or pet sitting. and weekends as well! i also offer custom rates depending how your pets is and if they need extra help and care. i’m willing to help parents who needs a pet sitter or dog walking and can’t afford high prices 😊.

Sitter Profile Image: Julie M.
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Julie M.
from
$18
per visit
5.0 out of 5 stars
• 2 reviews
1 repeat client
15 years of experience
Wooster Square, New Haven, CT, 06511

About: Hi! I've been dog-sitting for the past six years but I've also been around dogs my whole life. My family has always had one or two dogs since I was young, and I adopted my furr-baby, a black lab, border collie mix, when he was a puppy. I have experience with all types of dogs from an eight year old bichon frise to a two year old boxer-pitbull, elderly dogs that need medication and everything in between. I'm very active and enjoy walking/jogging (depending on the dog) and playing with the pups I'm watching. I absolutely love dogs and love dog-sitting as a way to spend time with pups while my dog is out of state with my parents for the time being (will be moving at the end of the year so he’s spending some time with his grandparents ☺️). Let me know if you have any questions! Look forward to hearing from you and making some new doggy friends! Thanks! I work from home and am able to give my pup (and yours!) lots of attention. AM and afternoon walks. Lots of potty breaks and PM hikes and dog park adventures. This is a very dog-friendly house and they’re welcome on furniture and beds. My dog is with my parents right now but my apartment is basically his with many parks and trails close by.

Sitter Profile Image: Jaylese H.
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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: Matthew M.
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Matthew M.
from
$30
per visit
16 years of experience
Hamden, CT, 06514

About: Been house/ pet siting for over 30 years. Have experience with dogs/ cats, small animals, and fish. Special diets, senior care, and pet meds administration. I’m currently retired and free to care for your fur babies anytime needed. Your fur baby is my biggest concern and receives my undivided attention. Have experience house/pet sitting with feeding, walking, potty breaks, crating, and all aspects of care. Special needs, and seniors are no issue. Every fur babies gets individual attention.

Sitter Profile Image: Caroline K.
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Caroline K.
from
$30
per visit
6 years of experience
North haven, CT, 06473

About: I have been pet sitting for over six years and have cared for animals for as long as I can remember. I have experience with a wide variety of animals, ranging from horses and lizards to dogs and cats. I currently have two dogs of my own, one is 4 years old and the other is 12. I understand the different needs pets may have at every stage of life. I am comfortable caring for dogs and cats of all sizes and temperaments and can administer oral medications when needed. I treat every pet as if they were my own and strive to make them feel safe, happy, and well cared for while you're away. I recently graduated from Fairfield University with my nursing degree and have begun my career as an emergency department nurse. My schedule is flexible, which allows me to accommodate a variety of pet care needs. You can count on me to be responsible, attentive, and dependable when caring for your pets. I will always make sure your pet has a clean, safe, and comfortable environment while in my care. When I arrive, I will ensure they have everything they need, including fresh water, food, exercise, and plenty of attention. Before I leave, I will make sure your home is tidy, your pet is safe, happy and comfortable. I will be sure to follow any instructions given to me prior to the visit. I will care for your pet as if they were my own and provide regular updates.

Sitter Profile Image: Charlotte B.
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Charlotte B.
from
$35
per visit
5.0 out of 5 stars
• 3 reviews
12 years of experience
North Haven, CT, 06473

About: I’ve taken care of dogs and worked in dog training for over a decade, and I’m comfortable with all sizes and breeds! I’ve also helped raise puppies to become guide dogs for the blind, and am experienced with senior dog care as well. I am a grad student and am available on weekdays, evenings, and weekends for pet sitting, house sitting, and dog walking! I can also be available on certain vacations and holiday breaks for pet sitting, house sitting, and dog walking. I’m comfortable working with dogs of all sizes, ages, and breeds. I have 12 years of dog sitting and dog training experience and am more than happy to stay at your home with your dog(s) in order to make sure all of their needs are met. I have cared for senior dogs primarily over the last five years, so I am very comfortable and experienced with older dogs and their specific needs. I also have experience administering medication to dogs both orally and topically.

Sitter Profile Image: Katie W.
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Katie W.
from
$25
per visit
5.0 out of 5 stars
• 26 reviews
7 repeat clients
10 years of experience
Watbury, CT, 06708

“Katie is absolutely amazing. We were having an incredibly stressful week and it was nice to know our dog was in great hands. Highly recommend, we’d love to have her watch Major again in the future.”

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Vivian R.
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: Aubrey K.
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Aubrey K.
from
$20
per visit
5.0 out of 5 stars
• 4 reviews
1 repeat client
15 years of experience
East Rock, New Haven, CT, 06511

About: My first “job” was dog sitting when I was in first grade. I included snuggling them every night in my promise to owners, and to this day nothing has changed. I work at the children’s hospital as a pediatric audiology extern from 7:30 am-6 pm every day. I would love to dog walk on weekday evenings and I am available to pet sit and dog walk on weekends. Pets’ safety is always the number one priority. With me, your pet will never be unattended or in dangerous situations. I also value other people’s space and home.

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!

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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
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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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