House Sitting Chester

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Over 2
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: Darylin L.
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Darylin L.
from
$45
per night
5.0 out of 5 stars
4 reviews
1 repeat client
15 years of experience
East Haddam, CT, 06423

Darylin was fantastic with Spanky, my 2 year old Basset Hound! It was the first time I’ve ever left him with anyone other than my son. She was great, sent me pictures, updates on his eating and treats. I would highly recommend her. Spanky was well cared for and very happy!!

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Dorothy M.
Sitter Profile Image: Serenity M.
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Serenity M.
Star Sitter
from
$60
per night
4.9 out of 5 stars
15 reviews
5 repeat clients
4 years of experience
Essex, CT, 06426

About: I’ve worked on farms and worked with multiple animal types from dogs to goats. I’m accustomed to schedule planning and checking everything off each day and night. I am open in the afternoons and I work in the early mornings. I am quite flexible as long as I have prior notice. My husband does come along with me to meet and greets and appointments when he is off work. I have a very relaxed home as I have my own puppy and she has full ranged of the entire apartment. She is fixed and potty trained.

Sitter Profile Image: Renana M.
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Renana M.
from
$100
per night
5.0 out of 5 stars
126 reviews
54 repeat clients
40 years of experience
Old Saybrook, CT, 06475

About: I've rescued and taken care of Animals for as long as I can remember and will care for your pets as if they’re my own. Please schedule drop offs and pick ups between 6 am and 6 pm. If you cannot pick up by 8 pm please book a sleepover. There’s a dog door that leads to the fenced back yard. I go outside with them to make sure they are safe. My home is only 600 sf so it’s easy to see everyone at all times! There are plenty of cozy spots for your dog to relax.

Sitter Profile Image: Jamie F.
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Jamie F.
from
$75
per night
5.0 out of 5 stars
8 reviews
1 repeat client
10 years of experience
Madison, CT, 06443

About: I have always grown up with dogs in my life, and wanted to be a Veterinarian since I was little. I have worked at multiple humane societies caring for the dogs, and have an array of experience through schooling, and an externship at a Pet Clinic. I care deeply for animals of all types, and I would like to spend the rest of my life ensuring their wellbeing, and protection. I am confident that I can provide quality care for your furry babies, and make sure they are comfortable and happy! I have a keen eye for observing their behaviors/tendencies, so this will be important if they seem to be in pain or discomfort. I only want the best for your pet since I understand the importance of their companionship. I am currently traveling, so looking for some gig work while I’m on the East Coast, but usually I’m living in Hawaii and am self-employed, so I have a lot of flexibility in my schedule. I make sure to be patient with each animal and let them come to me. I won’t force them to be social, and will be aware of their behaviors to ensure safety and trust is built between us. Also being mindful of their interactions with other dogs or humans if they have any issues with them.

Sitter Profile Image: Shannon E V.
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Shannon E V.
Star Sitter
from
$60
per night
5.0 out of 5 stars
37 reviews
11 repeat clients
7 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!

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Lauren G.
Sitter Profile Image: Kimberly G.
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Kimberly G.
Star Sitter
from
$100
per night
5.0 out of 5 stars
15 reviews
2 repeat clients
25 years of experience
Durham, CT, 06422

I would highly recommend Kim to care for your pet. We recently left our precious pooch for 2 weeks under Kim’s care. Kim stayed in our home and lovingly cared for our dog. Kim works remotely and was home with her which was important to us. She communicated daily and sent amazing pics which we loved. Our dog was relaxed and playful when we arrived home indicating the loving care she received. Our dog has frequently gone to the guest bedroom looking for Kim! Her care was above and beyond. It is such a good feeling to be able to travel and know your pet is in good hands.

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Anne H.
Sitter Profile Image: Patricia G.
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Patricia G.
from
$32
per night
4.6 out of 5 stars
9 reviews
4 repeat clients
45 years of experience
Waterford, CT, 06385

Trish was great with our three (kind of high maintenance) cats. They loved her immediately! She took good care of them and our house while we were out of town. We are so grateful that our cats loved her so much!

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Vanessa V.
Sitter Profile Image: Emily W.
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Emily W.
from
$95
per night
4.8 out of 5 stars
19 reviews
5 repeat clients
5 years of experience
Portland, CT, 06480

Emily house-sit our dog Amber for 4 days. I cannot recommend her enough and cannot wait to work with her again. First of all, she was able to stop by earlier in the day than I initially set the sitting for, and let Amber out midday and come back later to start the actual sitting. I hugely appreciated this since I made a mistake in the reservation start time. She was great with photo and text updates. From all the photos I could tell how happy Amber was. Her food and medication schedule was kept the same and she had lots of fun with Emily. And I have to say that the house was left immaculate. She went the extra mile to unload the dishwasher that I accidentally left in full, and took out all the trash. None of which were her responsibility but she truly went above and beyond and we appreciated all of it. We cannot wait to have her take care of Amber agan.

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sara m.
Sitter Profile Image: Kristen M.
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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.

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Lara G.
Sitter Profile Image: Elizabeth S.
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Elizabeth S.
from
$60
per night
5.0 out of 5 stars
8 reviews
15 years of experience
Colchester, CT, 06415

If I could give 10 stars I would! Elizabeth is absolutely amazing with pets and I highly recommend having her care for your pets. She was so engaging with all of my animals and sent pictures and updates, she’s incredibly kind and genuinely cares for your animals. She even came another time for me when I asked last minute and she was more than helpful to us. I am very grateful I found her and her services and will be using her again. Thank you so much Elizabeth!!!! ~Alyssa, Ben, Lili, Max and Lana <3

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Alyssa C.
Sitter Profile Image: Nikki B.
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Nikki B.
Star Sitter
from
$60
per night
5.0 out of 5 stars
25 reviews
9 repeat clients
6 years of experience
Middletown, CT, 06457

Nikkii was absolutely great. She sent pictures and kept me posted on how they were doing daily. My 2 crazy fur babies loved her and can't wait to see her again! Thank you for taking such great care of them

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Meagan E.
Sitter Profile Image: Kim B.
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Kim B.
from
$75
per night
5.0 out of 5 stars
48 reviews
23 repeat clients
30 years of experience
Haddam, CT, 06438

Kim did a great job taking care of my dog, cat, and house while I was away. She was responsible, attentive, and clearly cared for my pets as if they were her own. I came home to happy, well-cared-for animals. I highly recommend Kim to anyone looking for a reliable and caring pet and house sitter!

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James W.
Sitter Profile Image: Rebekah P.
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Rebekah P.
from
$50
per night
4.3 out of 5 stars
12 reviews
10 years of experience
Montville, CT, 06370

We were in a bind with a last minute cancellation and Becky was able to accommodate our request. She is quick to respond and is very attentive. She was patient with my pups as they warmed up to her and I'm pretty sure they have a new best friend. I highly recommend.

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Corrie W.
Sitter Profile Image: Esdras X.
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Esdras X.
from
$50
per night
4.5 out of 5 stars
7 reviews
1 repeat client
8 years of experience
Clinton, CT, 06413

Amazing! Very professional and personable. Would highly recommend him. Our pets were happy and he took great care of the house. I will definitely rehire him for our next getaway.

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Sarah G.
Sitter Profile Image: Faith L.
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Faith L.
Star Sitter
from
$60
per night
4.9 out of 5 stars
59 reviews
9 repeat clients
14 years of experience
Groton, CT, 06340

We really appreciate the good care from Faith for our pup Theo. She was prompt in responding, always conscientious, and everything went very smoothly while we were out of town.

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Scott M.
Sitter Profile Image: Grace V.
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Grace V.
from
$35
per night
5.0 out of 5 stars
2 reviews
6 years of experience
Madison, CT, 06443

This was our first time using Grace. She went above and beyond what was asked of her. I would highly recommend her to watch your house and pets. I plan to use her again.

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Amy S.
Sitter Profile Image: Roger B.
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Roger B.
from
$100
per night
5.0 out of 5 stars
94 reviews
14 repeat clients
28 years of experience
Westbrook, CT, 06498

Roger was wonderful. He stayed in communication with me the entire time we were away, sent pictures and left our home nice and neat. He went above and beyond in bringing in our trash and recycle barrels, mail and working to make sure our doodle was comfortable with him. We will definitely use again.

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Alaina K.
Sitter Profile Image: Palma T.
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Palma T.
from
$55
per night
5.0 out of 5 stars
33 reviews
6 repeat clients
25 years of experience
Norwich, CT, 06360

Palma was a wonderful sitter for our Scottie, Pepper! Pepper immediately befriended Palma when she came to meet us, and we could tell Palma was enjoying playing with Pepper. We felt very comfortable leaving Pepper in her hands. While we were away, Palma was very communicative and sent photos of Pepper for us (which I love because I always miss her). She left our house in pristine condition! I highly recommend Palma.

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Amanda W.
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

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: Christine V.
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Christine V.
from
$70
per night
4.9 out of 5 stars
224 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!

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Michele H.
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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

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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 $44.4 per night (as of September 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 September 2026, there are 1,426 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.

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