House Sitting in Cheshire

Find a loving house sitter to watch over your pets and your home.

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Top rated Cheshire house sitters

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Whitnee M.
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Whitnee M.
Star Sitter
from
$80
per night
5.0 out of 5 stars
22 reviews
6 repeat clients
14 years of experience
Meriden, CT, 06451

Whitnee was wonderful with our pugs during an overnight stay in our home while we were traveling. Highly recommended, and would absolutely hire again to take care of our girls.

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Preston M.
Sitter Profile Image: David P.
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David P.
Star Sitter
from
$85
per night
5.0 out of 5 stars
36 reviews
13 repeat clients
20 years of experience
Cheshire, CT, 06410

David stayed in our house with our dog and rabbit for a week while we were traveling and I could not recommend someone more highly. He was attentive to the needs of our pets and took my dog out on long walks at the park on a daily basis. He sent us pictures and updates frequently and took excellent care of our house. He took out the trash and even vacuumed our house before we came home! David is a one of a kind sitter who goes above and beyond. I will definitely ask him to come back in the future!

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Sandy P.
Sitter Profile Image: Arlene L.
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Arlene L.
from
$42
per night
5.0 out of 5 stars
7 reviews
4 years of experience
Meriden, CT, 06450

About: Hello! I've been an avid dog lover since I can remember. I have taken care of family and friends pups when they are away. My passion and the companions of a dog has made me want to own a dog of my own. I have my own pup of two years now and know how important it is to leave them with someone who will take great care of them, be safe and of course loved. I work remote Mon-Fri so trust me when I say I have plenty of time to play and walk your pup. They will be in great hands and company! During the weekends, I love taking my pup to an open yet dog secluded park to run, play, and train. I do have long leashes for safety, but if you are not comfortable with it- no worries at all, just please let me know. I'm also available most weekends for boarding per request. I have a pup of my own for your pups company as well! In my home I have a crate and can help with training if requested. The pups are free to roam around the apartment/furniture, and I take out to walk every two hours or so. Your pups will be in good hands, but I do request if your pup has a scheduled routine or specific needs/behaviors to please let me know so I can adjust to their needs and behaviors.

Sitter Profile Image: Sarah F.
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Sarah F.
from
$30
per night
5.0 out of 5 stars
4 reviews
1 repeat client
10 years of experience
Meriden, CT, 06450

Sarah was AMAZING! Incredibly accommodating. Fantastic, even though last minute. And took care of all FOUR of our fur-babies when we were out of town! Will definitely be using her in the future. Our favorite Rover sitter yet!

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Kirsten B.
Sitter Profile Image: Diana C.
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Diana C.
from
$60
per night
5.0 out of 5 stars
9 reviews
1 repeat client
3 years of experience
Wallingford, CT, 06492

About: Clear communication, consistent updates, and personalized care. I am comfortable following detailed care instructions, including medication schedules and specific routines. Can’t wait to meet your dog! -Diana I’m currently working from home part-time, so I’ll have plenty of time to play and take care of your pup! I’m available for boarding and walks weekdays and most weekends. I provide a clean, calm, and secure environment where your dog can feel comfortable and safe. I closely supervise all activities and ensure doors, gates, and surroundings are always secure.

Sitter Profile Image: Tiffany C.
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Tiffany C.
from
$32
per night
20 years of experience
Hamden, CT, 06518

About: Hi, my name is Tiffany, and I recently moved into the neighborhood. I wanted to take a moment to introduce myself and share a bit about what I do. I am an animal rescuer and a Connecticut-licensed wildlife rehabilitator, and I also offer dog walking and in-home pet sitting services. Animals are truly my passion, and I would love the opportunity to care for your furry family members. We also offer pet waste removal services for your yard. I work from home and dedicate my life to the care of pets of all species. This is my passion. I am very flexible and will take care of your baby as though they are my own. I have a large fenced in yard. I have a safe home. I also am available to take care of any pet within their own home as I know this is the most comfortable and stress-free for your fur baby.

Sitter Profile Image: Sara S.
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Sara S.
Star Sitter
from
$80
per night
5.0 out of 5 stars
35 reviews
10 repeat clients
10 years of experience
Wallingford, CT, 06492

Sara was very prompt, followed all instructions and very kind. She sent pics and updates. She asked questions of anything she was unsure of. One of my dogs requires medication and all went well. Highly recommend

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Marianne G.
Sitter Profile Image: Kailah J.
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Kailah J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
11 reviews
5 repeat clients
3 years of experience
Waterbury, CT, 06706

Kailah was beyond fabulous. She was punctual, accomodating, friendly, polite, and took marvelous care of my pup, providing multiple updates (text & photos)

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Pablo
Sitter Profile Image: Jade W.
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Jade W.
from
$45
per night
5.0 out of 5 stars
55 reviews
19 repeat clients
3 years of experience
Meriden, CT, 06450

Jade stayed at our place for a week watching our 2 pups and everything went great! We were kept up to date with pics and details of their days together and overall would recommend! Thanks again Jade!

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Devon R.
Sitter Profile Image: Kathryn R.
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Kathryn R.
from
$75
per night
5.0 out of 5 stars
34 reviews
9 repeat clients
22 years of experience
Meriden, CT, 06451

Kathryn was so communicative and thoughtful with our pets! Our big dog was being super stubborn due to being on new painkillers while we wait for our surgery date, and Kathryn was so patient and caring with our doggie. It’s always a good sign when our kitty warms up to her quickly too! Moana cat was in her lap immediately! 5/5 absolutely will recommend and already plan to use again!

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Emily S.
Sitter Profile Image: Michael F.
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Michael F.
from
$32
per night
15 years of experience
Cheshire, CT, 06410

About: If I can manage 30 middle schoolers, I can handle your dog." Hi there! My name is Michael, and I am a Cheshire local with 18 years of experience as a teacher, a dad of three kids, and most importantly — a dog dad of two. Caring for animals is not a side hustle for me; it is simply an extension of the way I live my life. My two dogs, Laney and Monster Truck, are at the center of our family. They go on walks, they cuddle on the couch, and yes — they are absolutely spoiled. When your pet stays with me, they become part of that same routine. What you can expect from me: 📍 Daily photo and text updates — I know you miss them. 🏡 A home environment with a yard, kids, and two friendly resident dogs. 🚶 Regular walks, playtime, and one-on-one attention. 🧠 Patience, structure, and consistency — 18 years in a classroom will do that to you. 💬 Clear, prompt communication before, during, and after every booking. A little more about our home: I am available primarily on weekends and summers, which means when I have your pet, I am fully present — not squeezing in visits between a 9-to-5. Your dog gets my undivided attention. I have experience with dogs of all sizes and energy levels. My own two dogs are a larger weiner dog and a medium sized hound/boxer mix, so I understand what it means to manage both ends of the spectrum. Whether you need a dog walker, a drop-in visit, or a full boarding stay while you travel, I would love to meet your pup. Let's set up a free meet-and-greet so your dog can check me out first. Your pet deserves someone who treats them like part of our pack. Pet care is already woven into my daily life. As a dog dad of two, my mornings start with a walk and my evenings end with one. Adding your pet to that routine is natural and effortless for our family. On weekends and during the summer — when I am available for bookings — I am home and fully present, which means your dog is never an afterthought. They are part of the day from start to finish. What you can expect from me: 📍 Daily photo and text updates — I know you miss them. 🏡 A home environment with a yard, kids, and two friendly resident dogs. 🚶 Regular walks, playtime, and one-on-one attention. 🧠 Patience, structure, and consistency — 18 years in a classroom will do that to you. 💬 Clear, prompt communication before, during, and after every booking.

Sitter Profile Image: Mckenzie P.
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Mckenzie P.
from
$32
per night
4 years of experience
Southington, CT, 06479

About: I have been dog and cat sitting for 4 years. I have 2 cats and a dog and I frequently dog sit for my neighbors! I am great with all ages of pets! I am currently a senior in highschool and I get out of school at 12:13 everyday. During the summer when school is out I have tons of availability. I have two cats of my own along with a dog and I love to play with them. I also love going outside with dogs and keeping them active!

Sitter Profile Image: Acadia C.
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Acadia C.
from
$55
per night
5.0 out of 5 stars
3 reviews
11 years of experience
North haven, CT, 06473

Archie was an amazing cat sitter for my two babies!! This is my first time using a pet sitter for my cats. I have a senior girl who was just recently diagnosed with IBD and requires a special diet and daily meds, and a rambunctious kitten who will do his darndest to be the cutest troublemaker you’ve ever met. Archie was amazing to work with, has extensive experience working with cats, and made me and my partner feel at ease! If you are looking for someone to watch over your feline friends, Archie is the best! I will definitely use them for future bookings.

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Patti R.
Sitter Profile Image: Ana V.
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Ana V.
from
$59
per night
5.0 out of 5 stars
2 reviews
17 years of experience
Cheshire, CT, 06410

Ana was amazing! I would def use her again. She was so kind to my puppies.

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valerie c.
Sitter Profile Image: Michael D.
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Michael D.
from
$60
per night
4.8 out of 5 stars
16 reviews
5 repeat clients
20 years of experience
Southington, CT, 06489

Michael was a wonderful pet sitter for our 4 dogs. He developed a great rapport with them and was super attentive to their needs. He took good notes for us and managed their schedules and took great care of our home as well! Michael stayed later than originally expected as we ran late getting back and was proactive in getting in touch with us and ensuring everyone was well taken care of!

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Amy L.
Sitter Profile Image: Sadie R.
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Sadie R.
from
$60
per night
5.0 out of 5 stars
11 reviews
1 repeat client
15 years of experience
Plantsvile, CT, 06479

Sadie is super responsive and friendly, sent plenty of pics of our pup while sitting and took great care of her while we were away. Highly recommended!

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Michael E.
Sitter Profile Image: Christopher C.
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Christopher C.
from
$95
per night
5.0 out of 5 stars
38 reviews
11 repeat clients
15 years of experience
Chesire, CT, 06410

Chris was absolutely fantastic. He was constantly communicating with us, sending pictures multiple times a day and reassuring us that our pets were doing great! He went above and beyond and exceeded our expectations. Would most definitely recommend Chris!

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Patrick H.
Sitter Profile Image: Stephanie O.
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Stephanie O.
from
$80
per night
5.0 out of 5 stars
27 reviews
7 repeat clients
5 years of experience
Wallingford, CT, 06492

Stephanie is absolutely wonderful with my 4 cats and 2 dogs! She is reliable, kind, and I know my fur babies are always in good hands. I can’t recommend her enough! Always worry free

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Ashley C.
Sitter Profile Image: Kenzie W.
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Kenzie W.
from
$65
per night
4.9 out of 5 stars
27 reviews
13 repeat clients
20 years of experience
Wallingford, CT, 06492

Kenzie was amazing! My oldest cat had been recently diagnosed with IBD and is on daily medication. To say he isn’t the easiest to pill is an understatement. Kenzie was able to give him his medication without fail and really eased my anxiety about being away! I would highly recommend her to anyone!

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Chelsea F.
Sitter Profile Image: Angela B.
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Angela B.
from
$90
per night
4.8 out of 5 stars
59 reviews
29 repeat clients
10 years of experience
Cheshire, CT, 06410

Angela was awesome!! This was our first time having a house sitter for two of our three dogs and we were a little nervous. Our dogs are great, but not always easy and can be troublemakers - Angela handled it like it was no big deal and always made us feel comfortable and confident that things were going well at home! We had 1 of our dogs with us, so their behavior was a little off as everything about this weekend was new for them, but Angela was patient and awesome with them! Angela was great with communication for questions, updates, & also made us feel at ease sending cuddle pictures & videos! One dog has food aggression - Angela was super great with following feeding structure to keep everyone safe so there were no attacks or aggressive behaviors...this was huge for us! We are working through separation anxiety with our other dog - Angela was great with giving his meds & patient when he managed to break out of his crate. We know they had a great weekend with her because we came home & they were excited to see us, but are acting 100% normal. We are so appreciative of Angela, her communication, attention to detail following our structure to keep everyone safe & her patience with our pups! We will definitely be asking her to house sit again!

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Lindsay M.
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Over 126
pet parents in Cheshire have booked house sitting

Cheshire pet parents share their Rover experiences

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5.0 out of 5 stars

Melissa was great! Both out pets loved her. She was great at giving updates and checking in. Will definitely use her in the future!

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KiAnna H.
House Sitting
5.0 out of 5 stars

Katherine was great! She was very responsive and always let me know what was going on. Plenty of pictures (I wish Rover would fix the app so you either get the pictures via text or have an easy way to download them as high res from the app itself) and my boys were well taken care of. I think they were a bit disappointed to see me walk in the door tonight instead of Katherine!

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Laura C.
House Sitting
5.0 out of 5 stars

Samantha was wonderful with my pets. Even my usually aloof cat was drawn to her lap right away. She cared for them attentively and left the house exactly as she found it. I wouldn’t have known anyone had stayed. She kept me updated with messages and photos, which made me feel completely at ease. Both I and my animals were very comfortable with her care. I would definitely hire her again!

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Trisha E.
House Sitting
5.0 out of 5 stars

Dave was great. He kept me well informed with both texts and pictures during my in-home watching. My dog received plenty of exercise and attention.

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John B.
House Sitting
5.0 out of 5 stars

Corbin was very professional, congenial and caring. He took great care of our Doggos and went above and beyond to accommodate our senior dogs, ‘swim therapy’ and extra items. I will definitely request for Corbin to come watch the pups and/or stay again.

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Carla O.
House Sitting
5.0 out of 5 stars

Excellent job and I would most definitely use Carly again. She cared for my nine-year-old labrador retriever, and I returned home to a very happy puppy. PS she doesn’t like spiders!

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Robert F.
House Sitting
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Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets 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 house sitting in Cheshire is $60

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

  • World-class support

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

Sitters in Cheshire average 3
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Cheshire on Rover as of Apr 2026 was about $60 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

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

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

As of Apr 2026, there are 1,336 house sitters in Cheshire. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 87% of Cheshire house sitters respond in under an hour.

House sitters in Cheshire have an average of 15 years of experience. House sitters with repeat customers have an average of 3 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Cheshire.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Cheshire house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

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

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