House Sitting Cheshire

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

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Over 50
pet parents in Cheshire have booked house sitting

Cheshire, Find top rated house sitting

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: David P.
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David P.
from
$85
per night
5.0 out of 5 stars
37 reviews
13 repeat clients
20 years of experience
Cheshire, CT, 06410

David was a professional from beginning to end. Connected beautifully with my dog, was on time, and did everything needed for Jasmine’s we’ll being. Will definitely be hiring him again at some point.

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Mitzi A.
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: Whitnee M.
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Whitnee M.
from
$80
per night
5.0 out of 5 stars
29 reviews
8 repeat clients
14 years of experience
Meriden, CT, 06451

Whitnee was great. So responsive and warm. She provided care during my wedding weekend and I couldn’t be more grateful for the help she provided so I could enjoy my special day!

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Amanda B.
Sitter Profile Image: Sadie R.
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Sadie R.
from
$60
per night
5.0 out of 5 stars
11 reviews
3 repeat clients
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: 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: Alexandra C.
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Alexandra C.
from
$40
per night
14 years of experience
Cheshire, CT, 06410

About: Grew up with four dogs and lifelong pet care experience. Trusted by clients & friends. Skilled with French Bulldogs and Dachshunds, including IVDD-aware handling. Attentive, reliable, communicative! Pet care easily fits into my routine. I have a flexible schedule and am available any day, ensuring pets receive reliable, attentive care whenever needed. I carefully follow each owner's instructions, maintain pets' routines, provide plenty of attention, exercise, feeding, medication if needed, and keep their home clean and secure.

Sitter Profile Image: Pippa L.
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Pippa L.
from
$50
per night
5 years of experience
Cheshire, CT, 06410

About: I love dogs so much. I have two big mutts on my own who I love. With college I haven’t been able to see them much, but looking forward with spending more time with other pups! I’m currently in graduate school for physical therapy but during the weekends and some weekdays I would love to spend my free time with some dogs! I have a fenced in yard with two mutts back at home. At school I have my own house with a few other house mates! I have taken care of multiple other dogs in their home over night and it is a lot of fun!

Sitter Profile Image: Tatum D.
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Tatum D.
from
$70
per night
5.0 out of 5 stars
4 reviews
2 repeat clients
10 years of experience
Meriden, CT, 06451

About: My name is Tatum I am 20 years old and have had exotic pets such as birds reptiles bugs and more. I currently have my own dog her name is Ripley and she’s almost a year old pit being trained for obedience and heel work I have training experience and dog care experience as I also used to work at a pet store caring for over 60 puppies at a time cleaning feeding playing with and giving medication! I currently am full time looking to fill up my schedule taking care of everyone’s animals feel free to ask questions and more ! Thank you I offer walks over night stays and I can do training and enrichment activities with your pup ! I’m also experienced with giving medications to sick dogs or seniors if needed

Sitter Profile Image: Sabrina & Daniel S.
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Sabrina & Daniel S.
Star Sitter
from
$100
per night
5.0 out of 5 stars
149 reviews
62 repeat clients
10 years of experience
Wallingford, CT, 06492

Repeat clients: We love the care and attention Sabrina and Daniel provide for our fur baby, Barney, and watching our house! Always wonderful, amazing photos (y’all have some incredible skills), and knowing Barney is happy. We will rebook again soon!! Barney, and we, are very appreciative for all you do!!

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Wendy R.
Sitter Profile Image: Sarah F.
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Sarah F.
from
$30
per night
5.0 out of 5 stars
7 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: Jade W.
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Jade W.
from
$45
per night
5.0 out of 5 stars
56 reviews
19 repeat clients
3 years of experience
Meriden, CT, 06450

We had to travel for our daughter's wedding. Lot's of planning and packing. I booked with Jade about a month out. He came and met the dogs. Absolutely delighted to come home freshly vacuumed floor and some very happy Doggies ..He kept us informed. It was so nice to not to stress about the dogs, knowing they were being well taken care of so we could enjoy this big event!

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Tracy 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

I am so happy I found Kenzie and so is Sheba! I now can go away and not worry about my animals. Kenzie is very responsible, trustworthy and an animal whisperer. I highly recommend her. Anne W.

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Anne W.
Sitter Profile Image: Justin B.
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Justin B.
from
$30
per night
10 years of experience
Wallingford, CT, 06492

About: I started taking care of pets when we got a family dog when I was a kid. Since then, I help my mom with her pet-sitting business and have sat for her 3 dogs for a week+ at a time. I genuinely love taking care of dogs of all ages. I work a full-time job 7-3 M-F, and have afternoon pilot classes about twice a week, always scheduled in advance. Occasionally I go out of town for a weekend, again, scheduled well in advance. I would treat a client's pet as if they were my own, which is to say with lots of love, care, patience, respect, and kindness. And a lot of head pats (if and when applicable).

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: 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

Christopher is great! We were so happy to leave our pup and cats in his care when we couldn’t be home. He was thoughtful and communicative. We loved getting photo and text updates of our happy pets while we were away. Thanks, Christopher!

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Courtney G.
Sitter Profile Image: Laura S.
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Laura S.
from
$60
per night
5.0 out of 5 stars
36 reviews
9 repeat clients
22 years of experience
Naugatuck, CT, 06770

I recently went away for 4 days and Laura watched my cat Felipe for me. As a first time cat owner and adopting Felipe almost 3 months ago, I was very nervous about leaving Felipe alone especially over night. Laura kept me updated the whole time, sent me pictures at every drop in to ease my worries and even did some extra drop ins to give him a little company. This was my first time using Laura as my cat sitter and she was absolutely amazing with Felipe. Thank you for taking such good care of my baby

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Jenise D.
Sitter Profile Image: Katelyn P.
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Katelyn P.
from
$55
per night
5.0 out of 5 stars
8 reviews
1 repeat client
17 years of experience
Meriden, CT, 06450

About: My name is Katelyn, and I’m a Pre-Vet student who has loved and cared for animals my entire life. I have professional experience as both a dog walker and a house sitter, and I’m comfortable caring for pets with a wide range of temperaments, routines, and special care needs. In addition, I work closely with a rescue organization where I’ve fostered many dogs and cats of all ages, gaining hands-on experience with young animals, socialization, and daily care. I recently graduated with a degree in Animal Science and a minor in Equine Studies, and I plan to continue pursuing my path toward veterinary school. Through both my education and hands-on experience, I’ve developed a strong foundation in animal behavior, handling, welfare, and medical care. Over the summers, I work as a veterinary technician, where I gain practical experience with animal health, safety, and clinical care. I’m comfortable caring for a wide range of species, and I treat every animal as if they were my own. I would truly love the opportunity to help care for your pets and give you peace of mind while you’re away! I am currently working part-time and have a pretty flexible schedule! I am available for house sitting or dog walking any day of the week. I always care for pets according to their normal routine and the owner’s preferences since consistency helps animals feel safe and comfortable. In a client’s home, I make sure pets are fed on time, have fresh water, get plenty of exercise or playtime, and receive lots of attention and positive interaction. I’m careful to follow any specific instructions for medications, diets, training cues, or household rules. I also make sure litter boxes, yards, and feeding areas stay clean. I like to keep owners updated with regular messages and photos so they know how their pet is doing. For shy or nervous pets, I am patient and let them warm up at their own pace. For energetic pets, I’m happy to provide extra play and enrichment. My goal is always to make pets feel relaxed, cared for, and loved while you’re away.

Sitter Profile Image: Nancy P.
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Nancy P.
from
$80
per night
5.0 out of 5 stars
18 reviews
9 repeat clients
10 years of experience
East Rock, Meriden, CT, 06450

Great job. On time and super professional. She made it a point to stay with our pup as much as possible. She sent pictures and was obviously playing with our high energy dog. She even ran the dishwasher as she left. I would highly recommend

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Kevin T.
Sitter Profile Image: Acadia C.
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Acadia C.
from
$55
per night
5.0 out of 5 stars
5 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: Enrique H.
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Enrique H.
from
$40
per night
5.0 out of 5 stars
2 reviews
6 years of experience
Waterbury, CT, 06795

About: I’ve had pets of all kind since the age of 4 and taken love for them since. I’ve had about 5 dogs, 4 birds 3 red ear slider turtles, multiple fishes and 1 cat throughout. I work full time as a properties manager. But in my spare time I would like to walk some dog as i truest enjoy walks, sitting and a fun time. I would care for your pest as if they were my own(of course respecting all your standards). Communication is key as I would like all expectations to be met and transparency across. To be trusted with a love one is a responsibility I take very seriously

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The median cost per night for house sitting in Cheshire is $60

Pet parents share their Rover experiences - Cheshire

1 / 1
5.0 out of 5 stars

Responsive. Took good care of our pups and our place. Did a great job. We would have no reservations booking her again.

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John S.
House Sitting
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
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Meet local sitters who will treat your pets like family

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Popular requests for house sitting - Cheshire

Select a filter and find qualifying sitters offering house sitting.

Sitters in Cheshire average 3
repeat house sitting clients

FAQs for House Sitting - Cheshire

Frequently asked questions about Rover

The average cost for House Sitting in Cheshire on Rover is $55.5 per night (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .

As of August 2026, there are 1,793 sitters on Rover offering House Sitting across Cheshire. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Cheshire walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Cheshire maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

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!

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.

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 .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

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

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

  • 94% of sitters can help with special care needs
  • 95% can help with giving oral medications or injections
  • 97% 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.

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