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 so great. He sent me regular updates on the girls and stayed with them throughout the day and night as I requested. He is by far the best petsitter on this site. Can't thank you enough David.

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Joan W.
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: Sadie R.
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Sadie R.
from
$60
per night
5.0 out of 5 stars
11 reviews
4 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: Justin B.
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Justin B.
from
$30
per night
5.0 out of 5 stars
4 reviews
1 repeat client
10 years of experience
Wallingford, CT, 06492

Justin was very nice and Alfie had a great time with him!

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Hohn N.
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

Simply put….Exceptional! I cannot give Kathryn enough praise. Our pets are our family and she took that to heart. She kept us updated the minute she walked in the door with pictures and texts. She rarely left their side and any concerns she had she contacted us ASAP! I would recommend her to anyone without hesitation and my pets loved her as much as we did!

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

Whitnee is always a reliable, kind companion to our pugs. Follows directions, provides updates, and treats our girls like they queens they are. Highly recommended!

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Preston M.
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: 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 stayed at our house over the week of Thanksgiving to take care of our 2 elder dogs, one which has some special needs and we couldn't have been happier with everything Chris did. He took excellent care of the pups (and our house), he was very detailed, responsible and treated our dogs as if they were his own. We have hired several dog sitters over the years and Chris is by far the best. He truly went above and beyond. Highly recommend him.

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Brendan Q.
Sitter Profile Image: Stephanie O.
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Stephanie O.
from
$80
per night
5.0 out of 5 stars
28 reviews
8 repeat clients
5 years of experience
Wallingford, CT, 06492

Stephanie was amazing watching my 2 dogs and 4 cats when I was away! She was in constant communication, always sending pictures and did a fantastic job! I definitely trust her and will use her again in the future!

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Ashley C.
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
154 reviews
62 repeat clients
10 years of experience
Wallingford, CT, 06492

Sabrina and Daniel were wonderful! It's clear that they are both dog smart, and they did a great job taking care of my pup, Poppy. Poppy has some anxiety and reactivity, and I felt comfortable and confident that Sabrina and Daniel would meet her needs. Plus, I loved the daily updates and photos while I was away. Thanks, Sabrina and Daniel!

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Lindsey T.
Sitter Profile Image: Jade W.
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Jade W.
from
$45
per night
5.0 out of 5 stars
56 reviews
20 repeat clients
3 years of experience
Meriden, CT, 06450

Jade has quickly become our savior helping us out with our new 12 week old puppy Lucy! He’s great with helping get her puppy energy out and handles the nipping stage with plenty of grace! We’re grateful he lets us have a break / tend to our work obligations while she’s still potty training and adjusting to everything and has been readily available to provide us support. We look forward to having Jade as someone we can continue to rely on long term for help with our energetic pup!

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Michelle M.
Sitter Profile Image: Laura L.
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Laura L.
from
$35
per night
5.0 out of 5 stars
6 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: Alex T.
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Alex T.
from
$65
per night
5.0 out of 5 stars
60 reviews
14 repeat clients
4 years of experience
North Haven, CT, 06473

Alex was kind and very quick to respond to my initial inquiry and when I checked in about how my dog/cat were doing.

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Jennifer B.
Sitter Profile Image: Sarah F.
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Sarah F.
from
$30
per night
5.0 out of 5 stars
8 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: Delaney B.
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Delaney B.
from
$60
per night
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: 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: Bethany C.
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Bethany C.
from
$70
per night
4.9 out of 5 stars
33 reviews
17 repeat clients
10 years of experience
Wallingford, CT, 06492

Bethany was great when she stayed with our dog over the weekend! She sent daily photos and updates and left the house just as clean as we left it! Will definitely be rebooking with her in the future!

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Kaylaa H.
Sitter Profile Image: Enrique H.
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Enrique H.
from
$40
per night
5.0 out of 5 stars
4 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

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 great with my dog. I could tell from the second they met that Kenzie had lots of time working with and being around dogs which gave me a lot of comfort that she could handle anything coming her way dealing with a puppy.

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Gregg S.
Sitter Profile Image: Katie J.
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Katie J.
from
$75
per night
5.0 out of 5 stars
11 reviews
2 repeat clients
15 years of experience
Naugatuck, CT, 06770

Katie did an absolutely phenomenal job taking care of my pup this past weekend!! It was a fairly last minute booking but I couldn't be happier. This was my first time using someone my {very anxious} dog Maverick wasn't familiar with and Katie won him over in record time! She provided excellent, timely updates with photos -- and dare I say Maverick even missed her as he was looking out the window all day yesterday! 10/10 recommend Katie and will absolutely be using her again! Thank you!!

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Tony K.
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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

Michael was fantastic to work with from start to finish. He was responsive, professional, and took the time to do a meet-and-greet beforehand so we could discuss Marley’s routine and make sure everyone was comfortable. During the visit, he followed our care instructions, spent quality time with Marley, and gave us peace of mind knowing he was in good hands. It’s clear he genuinely cares about the pets he looks after, and we appreciated his flexibility and communication throughout the process. We wouldn’t hesitate to book with Michael again and would gladly recommend him to anyone looking for a reliable, trustworthy sitter. Thanks again for taking such great care of our most prized family member!

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Christopher G.
House Sitting
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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Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • 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?

  • 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 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.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

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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