House Sitting Chester

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

End
Search

Over 9
pet parents in Chester have booked house sitting

Chester, 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.

1 / 1
Sitter Profile Image: Kat H.
Verified Enhanced Background Check
Kat H.
Star Sitter
from
$75
per night
5.0 out of 5 stars
35 reviews
14 repeat clients
10 years of experience
Deep River, CT, 06417

Kat was such a lifesaver! I decided to look for a sitter last-minute. She was very responsive and enthusiastic about meeting my guy. He was a little shy at first but Kat was super patient and kind. She sent photos throughout my visit and it was clear that they had a great time together. And I swear she left my home cleaner than I left it. She was wonderful and I'm so glad we found her. Highly recommend.

Profile image
Moira P.
Sitter Profile Image: Shannon E V.
Verified Enhanced Background Check
Shannon E V.
Star Sitter
from
$60
per night
5.0 out of 5 stars
34 reviews
10 repeat clients
6 years of experience
Marlborough, CT, 06447

Shannon watched our two huskies and stayed in our home while we were away for a weekend. She took excellent care of our home, collected our mail, and took the best care of our Doggos. She sent several picture updates of our dogs which helped immensely. We will definitely use her in the future and highly recommend her to others!

Profile image
Lauren G.
Sitter Profile Image: Roger B.
Verified Background Check
Roger B.
from
$100
per night
5.0 out of 5 stars
93 reviews
14 repeat clients
28 years of experience
Westbrook, CT, 06498

Roger is a fantastic dog watcher. We were away for 10 days and had Roger watch our two greyhounds in our home. We received daily photos of our dogs — walking, at rest, sitting, at attention, being happy — very happy. Also, the house was well cared for and was just as we left it. We plan on using Roger on a regular basis. Having him to depend on will give us more freedom and peace of mind.

Profile image
Lance J.
Sitter Profile Image: Cayton M.
Verified Enhanced Background Check
Cayton M.
Star Sitter
from
$85
per night
5.0 out of 5 stars
141 reviews
58 repeat clients
10 years of experience
Old Lyme, CT, 06371

Cayton watched our Great Dane at our house for 4 days. I had every confidence that she teated our dog like she were her own. She went above and beyond the time I expected her to be with her- I know she got lots of play time and snuggles. Being the first time, I was reassured with her texting and sending pictures. I will definitely have her watch Daisy again.

Profile image
Sue B.
Sitter Profile Image: Christine V.
Verified Background Check
Christine V.
from
$70
per night
4.9 out of 5 stars
222 reviews
90 repeat clients
15 years of experience
Middlefield, CT, 06455

Christine is a wonderful dog sitter! She stayed 9 days with our 2 high maintenance dogs and took excellent care of them. Christine’s communication both before and during our trip was exactly what we needed to feel comfortable. She sent pictures of our boys daily and sent us updates on their behaviors, eating, sleeping, and general wellbeing. It allowed us to relax and enjoy our trip!

Profile image
Michele H.
Sitter Profile Image: Kimberly G.
Verified Enhanced Background Check
Kimberly G.
Star Sitter
from
$100
per night
5.0 out of 5 stars
14 reviews
2 repeat clients
25 years of experience
Durham, CT, 06422

Kimberly is terrific! The dogs love her and the pictures she sends are literally 'frame worthy'! Such a treat to see my cuties having such a great time with her!

Profile image
Robin C.
Sitter Profile Image: Emily W.
Verified Enhanced Background Check
Emily W.
from
$95
per night
4.8 out of 5 stars
18 reviews
5 repeat clients
5 years of experience
Portland, CT, 06480

Emily was able to help us last minute to care for Amber after her surgery. She sent us messages and photos and when something was not right she immediately let me know and even helped me get her in the car. We truly appreciate her attention and care for Amber.

Profile image
sara m.
Sitter Profile Image: kathryn s.
Verified Enhanced Background Check
kathryn s.
Star Sitter
from
$50
per night
5.0 out of 5 stars
19 reviews
8 repeat clients
10 years of experience
East Lyme, CT, 06333

Kathryn took great care of our 2 beagles while we were away. I know they'll miss her. She even swept up(they are messy) and cleaned off the kitchen counters. We would definitely request her again, in fact we already did.

Profile image
phmurph@sbcglobal.net
Sitter Profile Image: Sierra J.
Verified Enhanced Background Check
Sierra J.
from
$40
per night
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Old Saybrook, CT, 06475

About: I've taken care of aniamls since I was 3, I take of my friends and neighbors animals, to give feed them and walk them and bathe them. I don't work because I live on a small farm and take care of them and all my dogs and birds and cats and I can work with anyone's pets after school. I have a dog fence with a doggy door for in and out and it's all fenced in and I have very friendly dogs that will Play and keep company.

Sitter Profile Image: Eden H.
Verified Enhanced Background Check
Eden H.
from
$55
per night
5.0 out of 5 stars
4 reviews
2 repeat clients
6 years of experience
Groton, CT, 06340

Eden was wonderful. Maya really took a liking to her. Will definitely be calling her again.

Profile image
Jody M.
Sitter Profile Image: Patricia G.
Verified Enhanced Background Check
Patricia G.
from
$32
per night
4.3 out of 5 stars
6 reviews
3 repeat clients
45 years of experience
Waterford, CT, 06385

About: Im very caring, respectful , I treat animals as my family. , always & forever, happiness is the key to healthiest animals, exercises and fun I work part-time but have evening time & weekends. Lots of love to give all animals, of all different sizes and personalities, I have lots of love and experience, i.also have Fridays available all day. I have 3 indoor cats that are my world. They have fresh water throughout the day, plenty of love & exercise, fun & lots of LOVE,

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

Sabrina and Daniel were great! They took such good care of my pups, communicated well, and left me feeling confident that my dogs and my home were in good hands while I was away. They also took some of the cutest photos of them that I've seen. :) Who knew I'd have souvenir photos of my dogs in addition to my vacation photos? I would recommend them highly. They are experienced dog-people who love what they do.

Profile image
Bridget N.
Sitter Profile Image: Faith L.
Verified Enhanced Background Check
Faith L.
Star Sitter
from
$60
per night
5.0 out of 5 stars
53 reviews
7 repeat clients
14 years of experience
Groton, CT, 06340

Once again, Faith gives above and beyond -/ sends photos of the babies, takes meticulous care of medications, leaves house spotless -- she is the best and we'd be lost without her.

Profile image
Courtney M.
Sitter Profile Image: Amy Z.
Verified Enhanced Background Check
Amy Z.
from
$75
per night
5.0 out of 5 stars
2 reviews
20 years of experience
Middletown, CT, 06457

Amy is great! Jasper had a lovely time with her and we got a good update in the morning before she left. I would book with her again and recommend her to anyone, not just those with a senior dog :)

Profile image
Molly D.
Sitter Profile Image: Nikki B.
Verified Enhanced Background Check
Nikki B.
from
$60
per night
5.0 out of 5 stars
24 reviews
9 repeat clients
6 years of experience
Middletown, CT, 06457

Nikki was terrific with my kitties as I was out of town for 8 days. She delivers and additionally left my home in tip-top shape. My cats were very well taken care of and calm upon my return. I could not ask for more.

Profile image
Lori S.
Sitter Profile Image: Jordan R.
Verified Enhanced Background Check
Jordan R.
from
$125
per night
5.0 out of 5 stars
55 reviews
25 repeat clients
8 years of experience
East Haven, CT, 06512

Jordan was fantastic. During the Meet & Greet, she asked all the right questions and it was very clear from the start that she is a professional who takes dog- and house-sitting seriously. We had her watched three large dogs for a full day and everything went smoothly. The dogs loved her and she kept us informed of how things were going. My daughter (two the three dogs were hers) also had high praise for Jordan. We will definitely seek out her services when we next need someone to watch Gracie.

Profile image
Rick M.
Sitter Profile Image: Anna F.
Verified Enhanced Background Check
Anna F.
from
$60
per night
5.0 out of 5 stars
41 reviews
10 repeat clients
6 years of experience
Waterford, CT, 06385

I am thrilled to have found Anna! She watched my puppy for an overnight stay and it was a great experience. Anna ensured she understood and followed all of my directions and checklists! Even though I am an over protective dog mom, Anna never made me feel over the top or like an inconvenience. She sent me photos and always asked questions if she had them! I am so excited I have found Anna and hope she can be my puppy’s primary dog sitter long term!

Profile image
Rebecca A.
Sitter Profile Image: Sitara A.
Verified Enhanced Background Check
Sitara A.
from
$60
per night
5.0 out of 5 stars
4 reviews
2 repeat clients
8 years of experience
Madison, CT, 06443

sitara is kind, patient, flexible...highly recommend

Profile image
Robert R.
Sitter Profile Image: Sarah E.
Verified Enhanced Background Check
Sarah E.
from
$63
per night
5.0 out of 5 stars
39 reviews
18 repeat clients
16 years of experience
Windsor, CT, 06095

We are so happy to have found Sarah! Throughout our getaway we got cute photo updates. Sarah left our house spotless! Our Barney can't wait to see you again!

Profile image
Pam H.
Sitter Profile Image: Kristen M.
Verified Enhanced Background Check
Kristen M.
from
$75
per night
5.0 out of 5 stars
3 reviews
1 repeat client
45 years of experience
Killingworth, CT, 06419

We are so happy with Kristen as a sitter for our 2 pups! She is experienced, attentive, and professional. Our dogs and house were in perfect form when we got home, and our dogs were not stressed at all. We look forward to using her regularly and having peace of mind when we go away.

Profile image
Lara G.
1 / 1
View more

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

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 - Chester

Select a filter and find qualifying sitters offering house sitting.

Sitters in Chester average 3
repeat house sitting clients

FAQs for House Sitting - Chester

Frequently asked questions about Rover

The average cost for House Sitting in Chester on Rover is $88.8 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 1,412 sitters on Rover offering House Sitting across Chester. 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 Chester 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 Chester 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 Chester 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 Chester. On Rover:

  • 92% 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.

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge